Datasets:

UniParser
/

RxnBench

question stringlengths 24 302	choices listlengths 4 4	answer int32 0 3	meta_info dict	question_type stringclasses 6 values
In Scheme 1C, what chemical processes do XAT and HAT refer to respectively? At which step of the reaction mechanism does each occur?	[ "XAT (halogen atom transfer) is halogen atom transfer, referring to the 4′-position iodinated sugar substrate undergoing halogen transfer with an amine radical or catalytic intermediate to generate a carbon radical, occurring in the later stage after radical addition; HAT (hydrogen atom transfer) is hydrogen atom t...	1	{ "title": "Photoredox-Catalyzed Site-Selective Intermolecular C(sp3)-H Alkylation of Tetrahydrofurfuryl Alcohol Derivatives", "journal": "ORGANIC LETTERS", "doi": "10.1021/acs.orglett.4c04439", "url": "https://pubs.acs.org/doi/10.1021/acs.orglett.4c04439" }	2
Please briefly describe the overall transformation process shown in Scheme 1C and the main reagents and conditions used.	[ "Scheme 1C shows a photocatalytically induced 1,5-HAT + intermolecular radical addition strategy: first, under blue LED irradiation, the photocatalyst (PC) is excited and undergoes single-electron transfer (SET) with an amine reductant, generating an amine radical; this radical, after deprotonation, further undergo...	0	{ "title": "Photoredox-Catalyzed Site-Selective Intermolecular C(sp3)-H Alkylation of Tetrahydrofurfuryl Alcohol Derivatives", "journal": "ORGANIC LETTERS", "doi": "10.1021/acs.orglett.4c04439", "url": "https://pubs.acs.org/doi/10.1021/acs.orglett.4c04439" }	2
Regarding the role of photocatalyst PC in the cyclical system of Scheme 1C and the energy and electron transfer processes, which of the following statements is correct?	[ "The photoexcited PC* oxidizes the amine to an amine radical cation via the first SET and generates PC˙+, after which PC˙+ undergoes electron transfer with the iodinated substrate to regenerate PC, but no proton transfer is involved.", "PC absorbs blue light to form the excited-state PC*, and via SET reduces the ...	1	{ "title": "Photoredox-Catalyzed Site-Selective Intermolecular C(sp3)-H Alkylation of Tetrahydrofurfuryl Alcohol Derivatives", "journal": "ORGANIC LETTERS", "doi": "10.1021/acs.orglett.4c04439", "url": "https://pubs.acs.org/doi/10.1021/acs.orglett.4c04439" }	2
What advantages does Scheme 1C have compared to the traditional ionic synthetic route (Scheme 1A)?	[ "Scheme 1C, via an ionic alkylation pathway, can rapidly accomplish carbon substitution at the 4′-position at high temperature, eliminating the use of photocatalysis and silyl‑iodide reagents, and enabling the in situ introduction of various substituents.", "This radical route, combining 1,5‑HAT and intramolecula...	2	{ "title": "Photoredox-Catalyzed Site-Selective Intermolecular C(sp3)-H Alkylation of Tetrahydrofurfuryl Alcohol Derivatives", "journal": "ORGANIC LETTERS", "doi": "10.1021/acs.orglett.4c04439", "url": "https://pubs.acs.org/doi/10.1021/acs.orglett.4c04439" }	3
Why choose alkenes bearing electron-withdrawing groups as acceptors for radical addition? How do different EWGs affect yield and stereoselectivity?	[ "EWGs (such as esters, nitriles, sulfonyl groups) can lower the HOMO energy level of the alkene, making radical addition faster and more regioselective, thereby increasing yield; the stronger the electron-withdrawing ability, the faster the addition and the better the yield; but when the group is too bulky or steri...	2	{ "title": "Photoredox-Catalyzed Site-Selective Intermolecular C(sp3)-H Alkylation of Tetrahydrofurfuryl Alcohol Derivatives", "journal": "ORGANIC LETTERS", "doi": "10.1021/acs.orglett.4c04439", "url": "https://pubs.acs.org/doi/10.1021/acs.orglett.4c04439" }	3
How is the active species LCuH regenerated in the cycle?	[ "LCuH is regenerated by protonation of LCuOtBu with t-BuOH: LCuOtBu + t-BuOH → LCuH + t-BuO⁻. This protonation step generates a copper alkoxide intermediate and replenishes LCuH, completing the catalytic cycle.", "LCuH is regenerated by β-hydride elimination from a carbon–copper intermediate (such as intermediate...	3	{ "title": "Access to Chiral Diamine Derivatives through Stereoselective Cu-Catalyzed Reductive Coupling of Imines and Allenamides", "journal": "JOURNAL OF ORGANIC CHEMISTRY", "doi": "10.1021/acs.joc.0c02971", "url": "https://pubs.acs.org/doi/10.1021/acs.joc.0c02971" }	2
Please briefly describe the overall sequence of the steps in this catalytic cycle	[ "The cycle begins with insertion of substrate 9a into LCuH (20) to give intermediate 21; intermediate 21 undergoes carbonate migration to form 23; 23 exchanges with the hydrosilane to regenerate LCuH and produce intermediate 24; then 24 is protonated by t-BuOH to give LCuOtBu (18a); finally NH4F removes the silyl p...	2	{ "title": "Access to Chiral Diamine Derivatives through Stereoselective Cu-Catalyzed Reductive Coupling of Imines and Allenamides", "journal": "JOURNAL OF ORGANIC CHEMISTRY", "doi": "10.1021/acs.joc.0c02971", "url": "https://pubs.acs.org/doi/10.1021/acs.joc.0c02971" }	2
Please describe the structural features of intermediate 21 and its role in the overall catalytic cycle.	[ "Intermediate 21 is an alkylcopper intermediate obtained by LCuH performing a face-selective 1,2-insertion (hydrocupration) into the alkene substrate 15a; it serves as a nucleophile and adds to carbonate 9a to give intermediate 22.", "Intermediate 21 is an alkylcopper intermediate obtained by LCuH performing a fa...	0	{ "title": "Access to Chiral Diamine Derivatives through Stereoselective Cu-Catalyzed Reductive Coupling of Imines and Allenamides", "journal": "JOURNAL OF ORGANIC CHEMISTRY", "doi": "10.1021/acs.joc.0c02971", "url": "https://pubs.acs.org/doi/10.1021/acs.joc.0c02971" }	2
What is the title of the catalytic cycle of this scheme?	[ "Proposed Catalytic Reaction Pathway", "Proposed Reaction Catalytic Cycle", "Proposed Reaction Catalytic Mechanism", "Scheme 3 Catalytic Reaction Cycle" ]	1	{ "title": "Access to Chiral Diamine Derivatives through Stereoselective Cu-Catalyzed Reductive Coupling of Imines and Allenamides", "journal": "JOURNAL OF ORGANIC CHEMISTRY", "doi": "10.1021/acs.joc.0c02971", "url": "https://pubs.acs.org/doi/10.1021/acs.joc.0c02971" }	0
Which reagent in the reaction system provides the Cu–H active species?	[ "The hydrosilane ([Si]–H) and LCuOR generate LCuH during the proton transfer process", "t-Butanol (t-BuOH) and LCuOtBu generate LCuH during the proton transfer process", "Ammonium fluoride (NH4F) and LCuOR generate LCuH during the proton transfer process", "LCuOtBu itself directly generates LCuH through decom...	0	{ "title": "Access to Chiral Diamine Derivatives through Stereoselective Cu-Catalyzed Reductive Coupling of Imines and Allenamides", "journal": "JOURNAL OF ORGANIC CHEMISTRY", "doi": "10.1021/acs.joc.0c02971", "url": "https://pubs.acs.org/doi/10.1021/acs.joc.0c02971" }	1
From a comparison of yields, the yield of the monohydroxylated product 9 is higher than that of product 8, while the dihydroxylated product 10 is the lowest. What could be the regioselectivity reasons behind this?	[ "The C11 site has higher electron density and lower steric hindrance, so it is more easily activated by O₂ to form a hydroxyl group; whereas the C3 site is surrounded by bulkier groups causing greater steric hindrance; dihydroxylation leads to competition between the product and the substrate for coordination, givi...	2	{ "title": "Structural Diversity of Perylenequinones Is Driven by Their Redox Behavior", "journal": "JOURNAL OF ORGANIC CHEMISTRY", "doi": "10.1021/acs.joc.1c02639", "url": "https://pubs.acs.org/doi/10.1021/acs.joc.1c02639" }	3
In the preliminary steps, which reducing agent is used to reduce the Q form of 1 to the HQ form?	[ "Sodium sulfite", "Sodium metabisulfite", "Sodium bisulfite", "Sodium sulfide" ]	1	{ "title": "Structural Diversity of Perylenequinones Is Driven by Their Redox Behavior", "journal": "JOURNAL OF ORGANIC CHEMISTRY", "doi": "10.1021/acs.joc.1c02639", "url": "https://pubs.acs.org/doi/10.1021/acs.joc.1c02639" }	1
What are the positions of the newly introduced hydroxyl groups and the respective yields for the reaction products 8, 9, and 10?	[ "Product 8 has a hydroxyl introduced at C11, yield 5%; product 9 has a hydroxyl introduced at C3, yield 4%; product 10 has hydroxyls introduced at both C3 and C11, yield 2%.", "Product 8 has a hydroxyl introduced at C11, yield 5%; product 9 has a hydroxyl introduced at C3, yield 6%; product 10 has hydroxyls intro...	1	{ "title": "Structural Diversity of Perylenequinones Is Driven by Their Redox Behavior", "journal": "JOURNAL OF ORGANIC CHEMISTRY", "doi": "10.1021/acs.joc.1c02639", "url": "https://pubs.acs.org/doi/10.1021/acs.joc.1c02639" }	0
What is the recovery rate of the quinone structure?	[ "5%", "2%", "60%", "6%" ]	2	{ "title": "Structural Diversity of Perylenequinones Is Driven by Their Redox Behavior", "journal": "JOURNAL OF ORGANIC CHEMISTRY", "doi": "10.1021/acs.joc.1c02639", "url": "https://pubs.acs.org/doi/10.1021/acs.joc.1c02639" }	0
What is the title of this chemical reaction diagram?	[ "Under aerobic conditions, generation of products 8–10 via oxidation of ent-Shiraiachrome A (1)（Generation of 8–10 via Oxidation of ent-Shiraiachrome A (1) under Aerobic Conditions）", "Under anaerobic conditions, generation of products 8–10 via reduction of ent-Shiraiachrome A (1)（Generation of 8–10 via Reduction...	2	{ "title": "Structural Diversity of Perylenequinones Is Driven by Their Redox Behavior", "journal": "JOURNAL OF ORGANIC CHEMISTRY", "doi": "10.1021/acs.joc.1c02639", "url": "https://pubs.acs.org/doi/10.1021/acs.joc.1c02639" }	0
According to Table 1, when the reaction conditions deviate from the original conditions and the reaction time is shortened to 15 minutes, what is the yield?	[ "When the reaction time was shortened to 15 minutes (Entry 4), the yield of product 3a dropped to 43%.", "When the reaction time was shortened to 15 minutes (Entry 4), the yield of product 3a dropped to 71%.", "When the reaction time was shortened to 15 minutes (Entry 4), the yield of product 3a dropped to 57%....	1	{ "title": "Modular Synthesis of Benzoylpyridines Exploiting a Reductive Arylation Strategy", "journal": "ORGANIC LETTERS", "doi": "10.1021/acs.orglett.3c03833", "url": "https://pubs.acs.org/doi/10.1021/acs.orglett.3c03833" }	0
Comparing the effects of different LED powers and wavelengths on yield	[ "Higher power (70 W) or bluer light (365 nm) caused the yield to decrease to 43% and 34%, respectively; whereas 44 W, 385 nm is the substrate's strongest absorption wavelength and suitable energy, giving the highest yield (95%).", "Lower power (20 W) or bluer light (385 nm) caused the yield to decrease to 43% and...	2	{ "title": "Modular Synthesis of Benzoylpyridines Exploiting a Reductive Arylation Strategy", "journal": "ORGANIC LETTERS", "doi": "10.1021/acs.orglett.3c03833", "url": "https://pubs.acs.org/doi/10.1021/acs.orglett.3c03833" }	3
Please describe the overall conversion process of this chemical reaction and the structural features of the product.	[ "Under irradiation by a 365 nm LED, this reaction performs a photochemical coupling of benzaldehyde with 4-cyanopyridine in the presence of base (DIPEA), producing a 1,1-diarylmethanol derivative whose central carbon is connected to a phenyl group on one side and to a pyridine ring on the other, and bears a hydroxy...	0	{ "title": "Modular Synthesis of Benzoylpyridines Exploiting a Reductive Arylation Strategy", "journal": "ORGANIC LETTERS", "doi": "10.1021/acs.orglett.3c03833", "url": "https://pubs.acs.org/doi/10.1021/acs.orglett.3c03833" }	2
Under what type of reactor and light source conditions was the reaction carried out? Please provide key information such as flow rate, temperature, and reaction time.	[ "The reaction was carried out in a Vapourtec continuous-flow reactor using a 44 W, 365 nm wavelength LED light source, with a solution concentration of 0.1 M in MeCN, flowed through the reactor (10 mL) at a flow rate of 0.33 mL/min, 25 °C, 3 minutes reaction time.", "The reaction was carried out in a Vapourtec co...	2	{ "title": "Modular Synthesis of Benzoylpyridines Exploiting a Reductive Arylation Strategy", "journal": "ORGANIC LETTERS", "doi": "10.1021/acs.orglett.3c03833", "url": "https://pubs.acs.org/doi/10.1021/acs.orglett.3c03833" }	0
What is the effect on the reaction in the dark or when the base is removed?	[ "The target product cannot be obtained either in the dark or when the base is removed.", "About 57% of the product can still be obtained when the base is removed, whereas in the dark the product disappears completely.", "A small amount of product can be obtained both in the dark and when the base is removed, bu...	0	{ "title": "Modular Synthesis of Benzoylpyridines Exploiting a Reductive Arylation Strategy", "journal": "ORGANIC LETTERS", "doi": "10.1021/acs.orglett.3c03833", "url": "https://pubs.acs.org/doi/10.1021/acs.orglett.3c03833" }	3
By what substrates are the different R groups introduced?	[ "Introduced via different carboxylic acid compounds (RCOOH) during the conversion of 1 to 3b", "Introduced via different hydrazine compounds (RNHNH2) during the conversion of 1 to 3b", "Introduced via different thiol compounds (RSH) during the conversion of 1 to 3b", "Introduced via different nitrile compound...	3	{ "title": "Solid-Phase Synthesis of s-Tetrazines", "journal": "ORGANIC LETTERS", "doi": "10.1021/acs.orglett.3c00955", "url": "https://pubs.acs.org/doi/10.1021/acs.orglett.3c00955" }	1
How are the R groups marked in blue in steps 3b to 5–10 in the figure manifested in the final products? Please briefly describe the types of these R groups.	[ "The blue R groups ultimately appear as substituted aryl groups on the tetrazole ring. In Scheme 2 the following R groups were examined in total: unsubstituted phenyl, 4-methoxyphenyl, 4-carboxyphenyl, 4-nitrophenyl and 4-fluorophenyl—five types of substituted aryl groups; additionally H, methyl and carboxymethyl w...	0	{ "title": "Solid-Phase Synthesis of s-Tetrazines", "journal": "ORGANIC LETTERS", "doi": "10.1021/acs.orglett.3c00955", "url": "https://pubs.acs.org/doi/10.1021/acs.orglett.3c00955" }	0
What is the E-SMILES of 4?	[ "COc1ccc(-c2nncnn2)cc1<sep>", "NC(=O)c1ccc(-c2nncnn2)cc1<sep>", "N#Cc1ccc(-c2nncnn2)cc1<sep>", "O=C(O)c1ccc(-c2nncnn2)cc1<sep>" ]	1	{ "title": "Solid-Phase Synthesis of s-Tetrazines", "journal": "ORGANIC LETTERS", "doi": "10.1021/acs.orglett.3c00955", "url": "https://pubs.acs.org/doi/10.1021/acs.orglett.3c00955" }	5
What role does sodium nitrite/2 M HCl play in this reaction?	[ "Sodium nitrite, under acidic conditions, reduces the dihydrotetrazine substrate to a more stable hydrogenated product, thereby producing tetrazine", "Sodium nitrite neutralizes with hydrochloric acid, adjusting the pH of the reaction system, thereby promoting product formation", "Sodium nitrite, under acidic c...	3	{ "title": "Solid-Phase Synthesis of s-Tetrazines", "journal": "ORGANIC LETTERS", "doi": "10.1021/acs.orglett.3c00955", "url": "https://pubs.acs.org/doi/10.1021/acs.orglett.3c00955" }	1
What solid-phase support resin and linker are used in Scheme 2? What advantages do they offer in the reaction design?	[ "This reaction uses ChemMatrix (CM) resin functionalized with a Wang amide linker. This linker can release the product under photolytic conditions, has good swelling and reaction efficiency, but its aqueous compatibility is poor, limiting multistep synthesis.", "This reaction uses polystyrene-based Wang resin fun...	2	{ "title": "Solid-Phase Synthesis of s-Tetrazines", "journal": "ORGANIC LETTERS", "doi": "10.1021/acs.orglett.3c00955", "url": "https://pubs.acs.org/doi/10.1021/acs.orglett.3c00955" }	1
Compared with route B which directly uses tyramine as the amination reagent, what advantages does route A’s use of the ammonium ion as the amination reagent have?	[ "Route A does not require a TBAF desilylation step and can obtain the product in one step, whereas route B must undergo two deprotection operations with TBAF and TFA.", "The NH4Cl ammonium ion in route A has higher nucleophilicity, allowing the reaction temperature to be lowered to 0°C, whereas route B requires t...	3	{ "title": "Pyrroloiminoquinone Alkaloids: Total Synthesis of Makaluvamines A and K", "journal": "ORGANIC LETTERS", "doi": "10.1021/acs.orglett.3c00350", "url": "https://pubs.acs.org/doi/10.1021/acs.orglett.3c00350" }	3
In the reaction in part A, what reagents, solvent and temperature conditions were used to convert 6b to intermediate 22?	[ "Excess ammonium chloride (NH4Cl), reacted in methanol (MeOH) at 0 °C to give intermediate 22, yield 56%", "Excess tetrabutylammonium fluoride (TBAF), reacted in methanol (MeOH) at 23 °C to give intermediate 22, yield 56%", "Excess ammonium chloride (NH4Cl), reacted in methanol (MeOH) at 23 °C to give intermedi...	2	{ "title": "Pyrroloiminoquinone Alkaloids: Total Synthesis of Makaluvamines A and K", "journal": "ORGANIC LETTERS", "doi": "10.1021/acs.orglett.3c00350", "url": "https://pubs.acs.org/doi/10.1021/acs.orglett.3c00350" }	0
What are the specific steps and product of step 2 in Part A? Please state the reagent, solvent, temperature, and the product name and yield.	[ "First remove the TES protecting group with TBAF in THF at 23 °C, then add trifluoromethanesulfonic acid/MeOH to protonate the indole nitrogen, finally obtaining Makaluvamine A (1), overall yield 69%.", "First remove the TES protecting group with tetramethylammonium fluoride in THF at 23 °C, then add TFA/MeOH to ...	3	{ "title": "Pyrroloiminoquinone Alkaloids: Total Synthesis of Makaluvamines A and K", "journal": "ORGANIC LETTERS", "doi": "10.1021/acs.orglett.3c00350", "url": "https://pubs.acs.org/doi/10.1021/acs.orglett.3c00350" }	0
What is the reaction title shown in part A of Scheme 7?	[ "Part A of Scheme 7 is the semisynthesis of Makaluvamine A (1)", "Part A of Scheme 7 is the total synthesis of Makaluvamine K (4)", "Part A of Scheme 7 is the total synthesis of Makaluvamine A (1)", "Part A of Scheme 7 is the deprotection step of Makaluvamine A (1)" ]	2	{ "title": "Pyrroloiminoquinone Alkaloids: Total Synthesis of Makaluvamines A and K", "journal": "ORGANIC LETTERS", "doi": "10.1021/acs.orglett.3c00350", "url": "https://pubs.acs.org/doi/10.1021/acs.orglett.3c00350" }	0
Why is it necessary in the synthesis of Makaluvamine A (1) to first remove the TES protecting group with TBAF and then protonate with TFA/MeOH?	[ "TBAF can efficiently remove the TES protecting group on the indole, exposing the reactive nitrogen; subsequently TFA/MeOH protonates the indole nitrogen and forms the trifluoroacetate salt, which is beneficial for product separation and stability.", "TBAF first protonates the indole nitrogen and activates the cy...	0	{ "title": "Pyrroloiminoquinone Alkaloids: Total Synthesis of Makaluvamines A and K", "journal": "ORGANIC LETTERS", "doi": "10.1021/acs.orglett.3c00350", "url": "https://pubs.acs.org/doi/10.1021/acs.orglett.3c00350" }	1
If the "capping" step is omitted after the coupling step, what effects will it have on the product purity and structure? Please explain why.	[ "If capping is omitted, the unreacted free 5'-OH will react with sulfurizing reagents during the sulfurization step to form thioether bonds, leading to thio-linked impurities in the chain and affecting product purity.", "If capping is omitted, the DMT protecting group on the unreacted residue cannot be completely...	2	{ "title": "Sustainability Challenges and Opportunities in Oligonucleotide Manufacturing", "journal": "JOURNAL OF ORGANIC CHEMISTRY", "doi": "10.1021/acs.joc.0c02291", "url": "https://pubs.acs.org/doi/10.1021/acs.joc.0c02291" }	1
In this cycle, what values can the group labeled Y take? What differences do they make in the final product?	[ "Y can be oxygen (O) or phosphorus (P). When Y = O a natural phosphodiester bond is formed; when Y = P a pentavalent phosphate ester bond is formed, and the pentavalent bond can enhance the oligonucleotide's binding ability and increase RNA recognition.", "Y can be oxygen (O) or nitrogen (N). When Y = O a natural...	3	{ "title": "Sustainability Challenges and Opportunities in Oligonucleotide Manufacturing", "journal": "JOURNAL OF ORGANIC CHEMISTRY", "doi": "10.1021/acs.joc.0c02291", "url": "https://pubs.acs.org/doi/10.1021/acs.joc.0c02291" }	3
What are the four basic steps of the oligonucleotide solid-phase synthesis cycle? Please briefly describe the main chemical change in each step.	[ "1. Detritylation (Detritylation): Use an organic acid (such as acetic acid) to remove the 4,4'-dimethoxytrityl (DMT) protecting group at the 5'-position of the solid-phase nucleoside, generating a free 5'-hydroxyl. 2. Coupling (Coupling): Use an activator (such as imidazole derivatives) to activate the phosphorami...	1	{ "title": "Sustainability Challenges and Opportunities in Oligonucleotide Manufacturing", "journal": "JOURNAL OF ORGANIC CHEMISTRY", "doi": "10.1021/acs.joc.0c02291", "url": "https://pubs.acs.org/doi/10.1021/acs.joc.0c02291" }	2
What is the chemical significance of oxidizing the intermediate from P(III) to P(V) after coupling? Why choose an oxidation or sulfurization step?	[ "P(III) intermediates are easily hydrolyzed and difficult to coexist with protecting groups; conversion to P(V) can facilitate DMTr removal and prevent ribose cyclization; oxidation (using sodium hypochlorite) produces the natural phosphate diester, sulfurization (using ammonium sulfate) produces sulfate esters, in...	2	{ "title": "Sustainability Challenges and Opportunities in Oligonucleotide Manufacturing", "journal": "JOURNAL OF ORGANIC CHEMISTRY", "doi": "10.1021/acs.joc.0c02291", "url": "https://pubs.acs.org/doi/10.1021/acs.joc.0c02291" }	1
Why is 4,4'-dimethoxytrityl (DMT) used as the protecting group for the 5'-hydroxyl? How is deprotection monitored online?	[ "When the DMT group is deprotected it releases a yellow trityl cation that exhibits strong absorption at approximately 560 nm. By online measurement of the yellow absorbance of the effluent, the efficiency of deprotection and reaction progress can be monitored in real time.", "When the DMT group is deprotected it...	1	{ "title": "Sustainability Challenges and Opportunities in Oligonucleotide Manufacturing", "journal": "JOURNAL OF ORGANIC CHEMISTRY", "doi": "10.1021/acs.joc.0c02291", "url": "https://pubs.acs.org/doi/10.1021/acs.joc.0c02291" }	1
Please give the Extended-SMILES (E-SMILES) expression of the small molecule (five-membered cyclic urea/lactam) labeled as the leaving product in Figure a.	[ "C1OC(=O)NC1<sep><a>0:R3</a>", "C1NC(=O)OC1<sep><a>0:R3</a>", "C1NC(=O)OC1<sep><a>1:R3</a>", "C1NC(=O)OC1<sep><a>0:R2</a>" ]	1	{ "title": "A Workflow Enabling the Automated Synthesis, Chain-End Degradation, and Rapid Mass Spectrometry Analysis for Molecular Information Storage in Sequence-Defined Oligourethanes", "journal": "JACS AU", "doi": "10.1021/jacsau.4c01070", "url": "https://pubs.acs.org/doi/10.1021/jacsau.4c01070" }	5
What base is used in the coupling step?	[ "DIPEA", "Fmoc-XXX-PNOC", "NMP", "HOBt" ]	0	{ "title": "A Workflow Enabling the Automated Synthesis, Chain-End Degradation, and Rapid Mass Spectrometry Analysis for Molecular Information Storage in Sequence-Defined Oligourethanes", "journal": "JACS AU", "doi": "10.1021/jacsau.4c01070", "url": "https://pubs.acs.org/doi/10.1021/jacsau.4c01070" }	0
What protecting group is used in Figure b? How is it deprotected?	[ "The protecting group used in Figure b is Fmoc (9-fluorenylmethoxycarbonyl), used to protect the amino group; in the final step deprotection was carried out with a mild 20% piperidine/DMA solution, a method widely used in solid-phase peptide synthesis.", "The protecting group used in Figure b is Fmoc (9-fluorenyl...	3	{ "title": "A Workflow Enabling the Automated Synthesis, Chain-End Degradation, and Rapid Mass Spectrometry Analysis for Molecular Information Storage in Sequence-Defined Oligourethanes", "journal": "JACS AU", "doi": "10.1021/jacsau.4c01070", "url": "https://pubs.acs.org/doi/10.1021/jacsau.4c01070" }	1
Which of the following statements about Figure c is correct?	[ "Figure c shows a sequence-controllable polymer encoding system constructed from amino acid monomers, similar to DNA and proteins, storing information through monomer sequences. The N-terminus is capped with an ethyl group to protect it and optimize mass spectrometry signal; Tyr(OMe) is a methoxy tyrosine residue, ...	3	{ "title": "A Workflow Enabling the Automated Synthesis, Chain-End Degradation, and Rapid Mass Spectrometry Analysis for Molecular Information Storage in Sequence-Defined Oligourethanes", "journal": "JACS AU", "doi": "10.1021/jacsau.4c01070", "url": "https://pubs.acs.org/doi/10.1021/jacsau.4c01070" }	0
Will the 5-exo-trig cyclization reaction in Figure a cycle infinitely along the polymer chain?	[ "It will not cycle infinitely; the reaction will occur simultaneously at every repeating unit of the polymer chain, causing the polymer to continuously contract and eventually degrade.", "This is the 5-exo-trig cyclization mechanism; as long as the basic environment is strong enough, the entire chain will continu...	3	{ "title": "A Workflow Enabling the Automated Synthesis, Chain-End Degradation, and Rapid Mass Spectrometry Analysis for Molecular Information Storage in Sequence-Defined Oligourethanes", "journal": "JACS AU", "doi": "10.1021/jacsau.4c01070", "url": "https://pubs.acs.org/doi/10.1021/jacsau.4c01070" }	2
How many aromatic carboxylic acids in the figure can produce the corresponding product?	[ "9", "12", "10", "14" ]	0	{ "title": "Reduction of Carboxylic Acids to Alcohols via Manganese(I) Catalyzed Hydrosilylation", "journal": "JACS AU", "doi": "10.1021/jacsau.1c00140", "url": "https://pubs.acs.org/doi/10.1021/jacsau.1c00140" }	3
Please describe the reaction conditions in detail, including the catalyst, reducing agent, solvent, temperature, and time.	[ "Catalyst: MnBr(CO)5 (5 mol %); Reducing agent: PhSiH3 (2.0–3.0 mmol); Solvent: tetrahydrofuran (THF, 0.5 mL); Reaction temperature: 80 °C; Reaction time: 2–16 h.", "Catalyst: MnBr(CO)5 (2 mol %); Reducing agent: PhSiH3 (2.0–3.0 mmol); Solvent: 2-methyltetrahydrofuran (2-MTHF, 0.5 mL); Reaction temperature: 80 °C...	1	{ "title": "Reduction of Carboxylic Acids to Alcohols via Manganese(I) Catalyzed Hydrosilylation", "journal": "JACS AU", "doi": "10.1021/jacsau.1c00140", "url": "https://pubs.acs.org/doi/10.1021/jacsau.1c00140" }	0
Please give examples of three aromatic carboxylic acid substrates and the yields of their corresponding alcohol products.	[ "1) 4-chlorobenzoic acid → 4-chlorobenzyl alcohol, yield 98 %; 2) 4-fluorobenzoic acid → 4-fluorobenzyl alcohol, yield 79 %; 3) 3-nitrobenzoic acid → 3-nitrobenzyl alcohol, yield 65 %.", "1) 4-methylbenzoic acid → 4-methylbenzyl alcohol, yield 68 %;\n2) 3,4-dimethoxybenzoic acid → 3,4-dimethoxybenzyl alcohol, yie...	1	{ "title": "Reduction of Carboxylic Acids to Alcohols via Manganese(I) Catalyzed Hydrosilylation", "journal": "JACS AU", "doi": "10.1021/jacsau.1c00140", "url": "https://pubs.acs.org/doi/10.1021/jacsau.1c00140" }	0
What is the overall transformation of this reaction? What are the main reactants and products, respectively?	[ "This is a hydrosilylation–hydrolysis reaction in which a carboxylic acid is reduced by a Mn catalyst and a hydrosilane to ultimately give the corresponding primary alcohol. The main reactants are aliphatic or aromatic carboxylic acids, using PhSiH₃ as the reductant, which under MnBr(CO)₅ catalysis first forms a si...	0	{ "title": "Reduction of Carboxylic Acids to Alcohols via Manganese(I) Catalyzed Hydrosilylation", "journal": "JACS AU", "doi": "10.1021/jacsau.1c00140", "url": "https://pubs.acs.org/doi/10.1021/jacsau.1c00140" }	2
Which carboxylic acid is difficult to form the corresponding product?	[ "o-Nitrobenzoic acid", "m-Nitrobenzoic acid", "p-Trifluoromethylbenzoic acid", "p-Nitrobenzoic acid" ]	1	{ "title": "Reduction of Carboxylic Acids to Alcohols via Manganese(I) Catalyzed Hydrosilylation", "journal": "JACS AU", "doi": "10.1021/jacsau.1c00140", "url": "https://pubs.acs.org/doi/10.1021/jacsau.1c00140" }	3
Please briefly describe the mechanism of the Vicarious Nucleophilic Substitution reaction, and specifically explain the role of thioesters or sulfonate esters in the mechanism.	[ "First, KHMDS forms a sodium salt with the thioester/sulfonate ester; this salt directly performs an SNAr substitution on the nitroarene, displacing the nitro group; subsequently the thioester departs to generate the alkylated product. The sulfone/sulfonate ester provides the nucleophilic carbon.", "First, KHMDS ...	1	{ "title": "Alkylation of Nitropyridines via Vicarious Nucleophilic Substitution", "journal": "ORGANIC LETTERS", "doi": "10.1021/acs.orglett.1c03920", "url": "https://pubs.acs.org/doi/10.1021/acs.orglett.1c03920" }	2
Please briefly describe the overall type of this reaction and what its core transformation process is?	[ "This reaction belongs to nucleophilic aromatic substitution (SNAr); the core is that a thiol containing an α-H is deprotonated by a strong base to generate a carbanion, which attacks the nitroarene aromatic ring, introducing an alkyl group and displacing thiophenol, yielding an alkylated nitroarene.", "This reac...	3	{ "title": "Alkylation of Nitropyridines via Vicarious Nucleophilic Substitution", "journal": "ORGANIC LETTERS", "doi": "10.1021/acs.orglett.1c03920", "url": "https://pubs.acs.org/doi/10.1021/acs.orglett.1c03920" }	2
What base, solvent, and temperature conditions are used in the reaction?	[ "Using 5.0 equivalents of KHMDS as a strong base, the solvent is THF, and the reaction is carried out at −40 °C for 30 min.", "Using 4.0 equivalents of KHMDS as a strong base, the solvent is DMF, and the reaction is carried out at −40 °C for 30 min.", "Using 5.0 equivalents of KHMDS as a strong base, the solven...	3	{ "title": "Alkylation of Nitropyridines via Vicarious Nucleophilic Substitution", "journal": "ORGANIC LETTERS", "doi": "10.1021/acs.orglett.1c03920", "url": "https://pubs.acs.org/doi/10.1021/acs.orglett.1c03920" }	0
What types of alkyl substituents were observed in the product examples?	[ "The examples include straight-chain alkyls (such as ethyl, propyl, pentyl), branched alkyls (such as isobutyl, tert-butyl), cyclohexylmethyl, oxygen-containing heterocyclic alkyls (such as tetrahydrofuran-2-yl), and nitrogen-containing heterocyclic alkyls such as piperidine.", "The examples include straight-chai...	2	{ "title": "Alkylation of Nitropyridines via Vicarious Nucleophilic Substitution", "journal": "ORGANIC LETTERS", "doi": "10.1021/acs.orglett.1c03920", "url": "https://pubs.acs.org/doi/10.1021/acs.orglett.1c03920" }	0
Which substituent is not present in the product with the highest yield?	[ "tert-Butyl", "Nitro", "Cl", "Phenylthio" ]	2	{ "title": "Alkylation of Nitropyridines via Vicarious Nucleophilic Substitution", "journal": "ORGANIC LETTERS", "doi": "10.1021/acs.orglett.1c03920", "url": "https://pubs.acs.org/doi/10.1021/acs.orglett.1c03920" }	0
How does the first-step reaction differ in outcome from the traditional Mukaiyama-type hydration reaction?	[ "Under the first-step reaction conditions shown in the figure, a racemate is obtained, whereas the Mukaiyama-type hydration under typical conditions has a dr of only about 1.2:1", "Under the first-step reaction conditions shown in the figure, a single stereoisomeric product is obtained, whereas the Mukaiyama-type...	2	{ "title": "Exploring the Chemical Space Accessed by Chiral Pool Terpenes. The (-)-Caryophyllene Oxide Paradigm", "journal": "ORGANIC LETTERS", "doi": "10.1021/acs.orglett.4c00132", "url": "https://pubs.acs.org/doi/10.1021/acs.orglett.4c00132" }	3
What is the role of adding TMSCl in the second step?	[ "Promote hydrolysis of the epoxide in 10 to form a hydroxyl, and eliminate the β-H to form a double bond", "Promote ring-opening of the epoxide in 10 to form a TMS-protected hydroxyl, and eliminate the β-H to form a double bond", "Promote ring-opening of the epoxide in 10 to form a hydroxyl, and eliminate the β...	3	{ "title": "Exploring the Chemical Space Accessed by Chiral Pool Terpenes. The (-)-Caryophyllene Oxide Paradigm", "journal": "ORGANIC LETTERS", "doi": "10.1021/acs.orglett.4c00132", "url": "https://pubs.acs.org/doi/10.1021/acs.orglett.4c00132" }	1
What is the title of the reaction route shown in this figure?	[ "Synthesis of Rumphellolide K and Rumphellaone A from camphene oxide", "Synthesis of Rumphellolide K and Rumphellaone A from (-)-camphene", "Synthesis of Rumphellolide K and Rumphellaone A from (-)-camphene oxide", "Synthesis of Rumphellolide K and Rumphellaone A from (+)-camphene oxide" ]	2	{ "title": "Exploring the Chemical Space Accessed by Chiral Pool Terpenes. The (-)-Caryophyllene Oxide Paradigm", "journal": "ORGANIC LETTERS", "doi": "10.1021/acs.orglett.4c00132", "url": "https://pubs.acs.org/doi/10.1021/acs.orglett.4c00132" }	0
What reagents and conditions were used in the first step of this route? What is the reaction type and purpose?	[ "Using p-nitrobenzoic acid, Fe(acac)3, PhSiH3, NaHCO3, MeOH, at -25°C. This is a hydration of a double bond, producing a tertiary alcohol.", "Using p-nitrobenzoic acid, Fe(acac)3, PhSiH3, NaHCO3, MeOH, at 0–25°C. This is a hydration of a double bond, producing a tertiary alcohol.", "Using p-nitrobenzoic acid, F...	1	{ "title": "Exploring the Chemical Space Accessed by Chiral Pool Terpenes. The (-)-Caryophyllene Oxide Paradigm", "journal": "ORGANIC LETTERS", "doi": "10.1021/acs.orglett.4c00132", "url": "https://pubs.acs.org/doi/10.1021/acs.orglett.4c00132" }	1
When epoxidizing an alkene with mCPBA, why can a single epoxide product be obtained with high stereoselectivity?	[ "Because the mCPBA molecule itself has considerable steric hindrance, it can only approach the double bond from one side and complete the epoxidation, ensuring the stereoselectivity of the product.", "A hydroxyl group in the cyclic framework forms a hydrogen bond with the chlorine atom of mCPBA, directionally gui...	3	{ "title": "Exploring the Chemical Space Accessed by Chiral Pool Terpenes. The (-)-Caryophyllene Oxide Paradigm", "journal": "ORGANIC LETTERS", "doi": "10.1021/acs.orglett.4c00132", "url": "https://pubs.acs.org/doi/10.1021/acs.orglett.4c00132" }	1
In the product examples, list one product that contains a bromine substituent and give the corresponding yield.	[ "Using product 2f (Ar–CH(OAc)CH2CH2CH2CH3, Ar bearing a bromine substituent) as an example, its yield is 49%.", "Using product 2e (Ar–CH(OAc)CH3, Ar bearing a bromine substituent) as an example, its yield is 44%.", "Using product 2b (Ar–CH(OAc)CH2CH2CH2CH3, Ar bearing a bromine substituent) as an example, its y...	1	{ "title": "Electrochemical Benzylic C(sp3)-H Acyloxylation", "journal": "ORGANIC LETTERS", "doi": "10.1021/acs.orglett.2c01930", "url": "https://pubs.acs.org/doi/10.1021/acs.orglett.2c01930" }	0
Please describe the overall transformation type and the key reaction processes of the electrochemical reaction shown in the figure.	[ "This reaction is an electrochemical oxidation of an aromatic ring C–H bond followed by acetate esterification; the substrate is a compound containing benzylic H, and the product is an aromatic acetate ester.", "This reaction is the electrochemical oxidation of a benzyl alcohol to benzaldehyde, which then undergo...	2	{ "title": "Electrochemical Benzylic C(sp3)-H Acyloxylation", "journal": "ORGANIC LETTERS", "doi": "10.1021/acs.orglett.2c01930", "url": "https://pubs.acs.org/doi/10.1021/acs.orglett.2c01930" }	2
What is the E-SMILES of the product containing a tert-butyl group	[ "O(C(C)=O)C(C)c1ccc(C(C)(C)C)cc1<sep>", "O(C(C)=O)C(CC)Cc1cccc(C(C)(C)C)c1<sep>", "O(C(C)=O)C(C)c1cccc(C(C)(C)O)c1<sep>", "O(C(C)=O)C(C)c1cccc(C(C)(C)C)c1<sep>" ]	3	{ "title": "Electrochemical Benzylic C(sp3)-H Acyloxylation", "journal": "ORGANIC LETTERS", "doi": "10.1021/acs.orglett.2c01930", "url": "https://pubs.acs.org/doi/10.1021/acs.orglett.2c01930" }	5
What reaction conditions and additives were used in this electrochemical acetoxylation reaction?	[ "The reaction was carried out in a DCM:AcOH = 3:1 (0.05 M) system, using constant current electrolysis at 10 mA, passing 2.5-7.5 F of charge during electrolysis, with 2,6-dimethylpyridine (0.1 M) as a proton buffer and supporting electrolyte, ultimately obtaining the desired product.", "The reaction was carried o...	1	{ "title": "Electrochemical Benzylic C(sp3)-H Acyloxylation", "journal": "ORGANIC LETTERS", "doi": "10.1021/acs.orglett.2c01930", "url": "https://pubs.acs.org/doi/10.1021/acs.orglett.2c01930" }	0
Which product can be prepared from ibuprofen, and what is the yield?	[ "2h, yield is 48%", "2e, yield is 44%", "2b, yield is 49%", "2k, yield is 49%" ]	3	{ "title": "Electrochemical Benzylic C(sp3)-H Acyloxylation", "journal": "ORGANIC LETTERS", "doi": "10.1021/acs.orglett.2c01930", "url": "https://pubs.acs.org/doi/10.1021/acs.orglett.2c01930" }	0
If R3 is a nitro group, what effect does it have on the reaction?	[ "The product is unstable and easily degrades", "Yield is increased compared to H", "Cannot be determined", "Yield decreases significantly" ]	3	{ "title": "Heterohelicenes through 1,3-Dipolar Cycloaddition of Sydnones with Arynes: Synthesis, Origins of Selectivity, and Application to pH-Triggered Chiroptical Switch with CPL Sign Reversal", "journal": "JACS AU", "doi": "10.1021/jacsau.1c00084", "url": "https://pubs.acs.org/doi/10.1021/jacsau.1c00084" }	3
Please describe in detail the general formula of this reaction, including the reactants, catalyst, base, solvent, temperature, and product.	[ "The general formula is a sydnone bearing a variable R1 substituent reacting with 2-bromophenone derivatives under Pd(OAc)2/PPh3 catalysis, KHCO3 as the base and DMF as the solvent, at 80 or 120 °C, to give fused aryl-annulated substituted sydnone products.", "The general formula is a sydnone bearing a variable R...	3	{ "title": "Heterohelicenes through 1,3-Dipolar Cycloaddition of Sydnones with Arynes: Synthesis, Origins of Selectivity, and Application to pH-Triggered Chiroptical Switch with CPL Sign Reversal", "journal": "JACS AU", "doi": "10.1021/jacsau.1c00084", "url": "https://pubs.acs.org/doi/10.1021/jacsau.1c00084" }	0
Please write the E-SMILES representation of sydnone substrates (type I substrate).	[ "C(C1C(Br)=CC=CC=1)=O<sep><a>0:R[2]</a><r>0:R[3]</r>", "C[n+]1[n-]oc(=O)c1<sep><a>0:R[1]</a>", "*C[n+]1[n-]oc(=O)c1<sep><r>0:R[1]</r>", "C[n+]1[n-]oc(=O)c1<sep><r>0:R[1]</r>" ]	1	{ "title": "Heterohelicenes through 1,3-Dipolar Cycloaddition of Sydnones with Arynes: Synthesis, Origins of Selectivity, and Application to pH-Triggered Chiroptical Switch with CPL Sign Reversal", "journal": "JACS AU", "doi": "10.1021/jacsau.1c00084", "url": "https://pubs.acs.org/doi/10.1021/jacsau.1c00084" }	5
What is the R3 substituent in the aryl ketone substrate corresponding to the product with the highest yield?	[ "F", "H", "methyl", "Cl" ]	1	{ "title": "Heterohelicenes through 1,3-Dipolar Cycloaddition of Sydnones with Arynes: Synthesis, Origins of Selectivity, and Application to pH-Triggered Chiroptical Switch with CPL Sign Reversal", "journal": "JACS AU", "doi": "10.1021/jacsau.1c00084", "url": "https://pubs.acs.org/doi/10.1021/jacsau.1c00084" }	0
What is the title of this chemical reaction scheme? Briefly state the research objective.	[ "The title is \"Sydnone Preparation\", and the research objective is to couple substituted sydnones with 2-bromobenzoyl derivatives via a palladium-catalyzed arylation reaction to construct polyaryl-substituted sydnone derivatives.", "The title is \"Arylation of Sydnone\", and the research objective is to couple ...	0	{ "title": "Heterohelicenes through 1,3-Dipolar Cycloaddition of Sydnones with Arynes: Synthesis, Origins of Selectivity, and Application to pH-Triggered Chiroptical Switch with CPL Sign Reversal", "journal": "JACS AU", "doi": "10.1021/jacsau.1c00084", "url": "https://pubs.acs.org/doi/10.1021/jacsau.1c00084" }	0
If the aldehyde substrate R–CHO is replaced by a ketone R₂C=O, how would the formation of the Breslow intermediate be affected? Please explain why.	[ "Ketones, compared to aldehydes, have higher electrophilicity and smaller steric hindrance, so the NHC more readily undergoes nucleophilic addition to them, thereby accelerating the formation rate of the Breslow intermediate and increasing catalytic efficiency and yield.", "Ketones and aldehydes do not differ muc...	2	{ "title": "Redox Active N-Heterocyclic Carbenes in Oxidative NHC Catalysis", "journal": "ORGANIC LETTERS", "doi": "10.1021/acs.orglett.4c00731", "url": "https://pubs.acs.org/doi/10.1021/acs.orglett.4c00731" }	3
In the catalytic cycle of Scheme 4, what steps does Breslow intermediate I undergo to be converted into acylazolium intermediate III?	[ "Breslow intermediate I directly undergoes electron transfer with the iron porphyrin catalyst to generate acylazolium intermediate III, without passing through intermediate II", "Breslow intermediate I is first oxidized to form intermediate II, and then undergoes a second proton transfer with a base to generate I...	2	{ "title": "Redox Active N-Heterocyclic Carbenes in Oxidative NHC Catalysis", "journal": "ORGANIC LETTERS", "doi": "10.1021/acs.orglett.4c00731", "url": "https://pubs.acs.org/doi/10.1021/acs.orglett.4c00731" }	2
List the three key intermediates in the NHC catalytic cycle in Scheme 4, and briefly describe their structural features.	[ "1. Free carbene: a divalent carbon formed on the imidazole ring, bearing a lone pair of electrons, can act as a strong nucleophile to attack the aldehyde.\n2. Breslow intermediate: the α-hydroxy enaminol ion pair formed after the free carbene reacts with the aldehyde; the intermediate exhibits an enamine double bo...	0	{ "title": "Redox Active N-Heterocyclic Carbenes in Oxidative NHC Catalysis", "journal": "ORGANIC LETTERS", "doi": "10.1021/acs.orglett.4c00731", "url": "https://pubs.acs.org/doi/10.1021/acs.orglett.4c00731" }	2
Please briefly describe the overall reaction equation of the catalytic cycle proposed in Scheme 4, including the main reactants, catalysts, oxygen and the main products.	[ "The overall reaction equation of this catalytic cycle is: R–CHO (aldehyde) + Nu (nucleophile) + 1/2 O₂ + NHC precatalyst (4a) + FePc (iron phthalocyanine) + base → R–CO–Nu (acylation product) + H₂O. The NHC catalytic system is responsible for activation of the aldehyde and acyl transfer, and the FePc/O₂ system is ...	0	{ "title": "Redox Active N-Heterocyclic Carbenes in Oxidative NHC Catalysis", "journal": "ORGANIC LETTERS", "doi": "10.1021/acs.orglett.4c00731", "url": "https://pubs.acs.org/doi/10.1021/acs.orglett.4c00731" }	2
Why is it necessary for FePc to be used together with O₂ in this catalytic cycle, rather than using O₂ directly to oxidize the Breslow intermediate?	[ "Using O₂ alone to directly oxidize the Breslow intermediate is extremely inefficient, has large kinetic barriers, and easily produces by-products. FePc, as a transition metal catalyst, can lower the barrier for electron transfer and activate O₂ into a highly reactive intermediate, thus efficiently and mildly achie...	0	{ "title": "Redox Active N-Heterocyclic Carbenes in Oxidative NHC Catalysis", "journal": "ORGANIC LETTERS", "doi": "10.1021/acs.orglett.4c00731", "url": "https://pubs.acs.org/doi/10.1021/acs.orglett.4c00731" }	1
In Takemoto (2022)'s example, what are the yields of products 3b and 3c from substrate 3a, respectively?	[ "Under toluene reflux conditions, after the Claisen rearrangement of 3a the major product 3b has a yield of 78% and the minor product 3c has a yield of 12%.", "Under toluene reflux conditions, after the Claisen rearrangement of 3a the major product 3b has a yield of 74% and the minor product 3c has a yield of 20%...	1	{ "title": "Directing the Stereoselectivity of the Claisen Rearrangement to Form Cyclic Ketones with Full Substitution at the α-Positions", "journal": "ORGANIC LETTERS", "doi": "10.1021/acs.orglett.3c02752", "url": "https://pubs.acs.org/doi/10.1021/acs.orglett.3c02752" }	0
In the Xu (2022) example, what reaction conditions were used in the two steps from substrate 1a to product 1c?	[ "In the first step, Pd(PPh₃)₄-catalyzed allyl acetate reacted with 1a in an appropriate solvent (such as DCE) to give the allyl ether intermediate 1b; in the second step 1b was dissolved in benzene and the Claisen rearrangement was carried out under microwave conditions at 175 °C to give product 1c (overall yield f...	3	{ "title": "Directing the Stereoselectivity of the Claisen Rearrangement to Form Cyclic Ketones with Full Substitution at the α-Positions", "journal": "ORGANIC LETTERS", "doi": "10.1021/acs.orglett.3c02752", "url": "https://pubs.acs.org/doi/10.1021/acs.orglett.3c02752" }	0
In the reaction mechanism of this work, which step determines the formation of the enantiomer (enantio)? Which step determines the formation of the diastereomer (diastereo)?	[ "In the first step, the addition of the nucleophile–metal–chiral-ligand complex to the substrate simultaneously determines both the enantiomer (enantio-determining) and the diastereomer (diastereo-determining), while the Claisen rearrangement step only provides a thermodynamic drive and does not change the stereoch...	3	{ "title": "Directing the Stereoselectivity of the Claisen Rearrangement to Form Cyclic Ketones with Full Substitution at the α-Positions", "journal": "ORGANIC LETTERS", "doi": "10.1021/acs.orglett.3c02752", "url": "https://pubs.acs.org/doi/10.1021/acs.orglett.3c02752" }	2
What is the title of this chart?	[ "Governing Diastereoselectivity in the Formation of Quaternary Centers via the Cope Rearrangement", "Governing Enantioselectivity in the Formation of Quaternary Centers via the Claisen Rearrangement", "Regulating Diastereoselectivity in the Formation of Quaternary Centers via the Claisen Rearrangement", "Gove...	3	{ "title": "Directing the Stereoselectivity of the Claisen Rearrangement to Form Cyclic Ketones with Full Substitution at the α-Positions", "journal": "ORGANIC LETTERS", "doi": "10.1021/acs.orglett.3c02752", "url": "https://pubs.acs.org/doi/10.1021/acs.orglett.3c02752" }	0
Why, in Soós (2016)'s example, are products 4b and 4c formed in a 1:1 ratio in the absence of a catalyst, while this method can achieve high selectivity?	[ "In Soós' study inorganic Lewis acid catalysis was used, causing the coordination between substrate and catalyst to be unable to distinguish different transition states, leading to 4b and 4c being formed in a 1:1 ratio; whereas this method achieves high enantioselectivity through a chiral Brønsted acid.", "In the...	2	{ "title": "Directing the Stereoselectivity of the Claisen Rearrangement to Form Cyclic Ketones with Full Substitution at the α-Positions", "journal": "ORGANIC LETTERS", "doi": "10.1021/acs.orglett.3c02752", "url": "https://pubs.acs.org/doi/10.1021/acs.orglett.3c02752" }	3
By a 13CO2 labeling experiment, how can one demonstrate that each carboxyl group is derived from CO2?	[ "Introduce pure 13CO2 (1 atm) into the reaction; both carboxyl groups in product 2a show absorption peaks at 1705 cm⁻¹ in the FT-IR, proving that each carboxyl group comes from CO2.", "Introduce pure 13CO2 (1 atm) into the reaction; in the resulting product 2a the 13C NMR signals of both carboxyl groups indicate ...	1	{ "title": "Nickel Catalyzed Carbonylation/Carboxylation Sequence via Double CO2 Incorporation", "journal": "ORGANIC LETTERS", "doi": "10.1021/acs.orglett.3c02394", "url": "https://pubs.acs.org/doi/10.1021/acs.orglett.3c02394" }	2
What are the structural features of product 2a and the results of the 13C labeling experiment?	[ "Product 2a is a carboxylic acid containing a bridged aromatic group; both of its carbonyls originate from AlCl₃-activated CO₂, and the labeling experiment shows one carbonyl's ¹³C abundance is >95%, while the other is about 50%.", "Product 2a is a carboxylic acid containing a bridged aromatic group; both carbony...	1	{ "title": "Nickel Catalyzed Carbonylation/Carboxylation Sequence via Double CO2 Incorporation", "journal": "ORGANIC LETTERS", "doi": "10.1021/acs.orglett.3c02394", "url": "https://pubs.acs.org/doi/10.1021/acs.orglett.3c02394" }	0
What is the overall reaction type and title of this reaction?	[ "This reaction is a Ni/Al bimetallic cooperative-catalyzed dicarbonylation of acyclic alkenes, and the title can be stated as \"Mechanistic study of Ni/Al dual catalysis for double CO₂ insertion into acyclic alkenes to produce dicarbonylated compounds\".", "This reaction is a Ni/Al bimetallic cooperative-catalyze...	3	{ "title": "Nickel Catalyzed Carbonylation/Carboxylation Sequence via Double CO2 Incorporation", "journal": "ORGANIC LETTERS", "doi": "10.1021/acs.orglett.3c02394", "url": "https://pubs.acs.org/doi/10.1021/acs.orglett.3c02394" }	2
What is the oxidation state of Ni at the start of the reaction?	[ "The initiating species is LNiBr, Ni is in the +1 oxidation state", "The initiating species is LNiCl, Ni is in the +1 oxidation state", "The initiating species is Ni(0)L, Ni is in the 0 oxidation state", "The initiating species is LNiCl2, Ni is in the +2 oxidation state" ]	1	{ "title": "Nickel Catalyzed Carbonylation/Carboxylation Sequence via Double CO2 Incorporation", "journal": "ORGANIC LETTERS", "doi": "10.1021/acs.orglett.3c02394", "url": "https://pubs.acs.org/doi/10.1021/acs.orglett.3c02394" }	0
Which of the following options is correct regarding the roles of the main catalysts and reagents in this reaction system and the reaction conditions?	[ "The reaction uses [Ni(L1)₂]Cl₂ (10 mol%) as the nickel catalyst, AlCl₃ is used to coordinate and immobilize the Ni center, ZnClBr/ZnCl₂(DMF)₄ are used to activate CO₂, and Zn is used to stabilize the Ni(0) intermediate. The reaction is carried out in DMF solvent at 45 °C under 1 atm CO₂, and the product yield is 5...	1	{ "title": "Nickel Catalyzed Carbonylation/Carboxylation Sequence via Double CO2 Incorporation", "journal": "ORGANIC LETTERS", "doi": "10.1021/acs.orglett.3c02394", "url": "https://pubs.acs.org/doi/10.1021/acs.orglett.3c02394" }	1
In the 'aromatic and heteroaromatic' substrate set, choose any three examples and give the yields of their TMS-derivatized products.	[ "For example: 4-methoxyphenylacetylene → 2c, yield 92%; 3,5-difluorophenylacetylene → 2i, yield 85%; 2-ethynylpyridine → 2k, yield 75%.", "For example: 4-methoxyphenylacetylene → 2c, yield 85%; 3,5-difluorophenylacetylene → 2i, yield 92%; 2-ethynylpyridine → 2k, yield 69%.", "For example: 4-methoxyphenylacetyle...	1	{ "title": "Carboxylate-Catalyzed C-Silylation of Terminal Alkynes", "journal": "ORGANIC LETTERS", "doi": "10.1021/acs.orglett.3c04213", "url": "https://pubs.acs.org/doi/10.1021/acs.orglett.3c04213" }	0
Please briefly describe the overall transformation of this reaction and the catalyst and reaction conditions used.	[ "The reaction is a nucleophilic silylation of terminal alkynes with N,O-bis(trimethylsilyl)acetamide (BSA) or the corresponding silane reagent in acetonitrile, catalyzed by a carboxylate (TMAP, 10 mol%), carried out from −10 °C to room temperature, to give the corresponding TMS-protected alkyne products.", "The r...	0	{ "title": "Carboxylate-Catalyzed C-Silylation of Terminal Alkynes", "journal": "ORGANIC LETTERS", "doi": "10.1021/acs.orglett.3c04213", "url": "https://pubs.acs.org/doi/10.1021/acs.orglett.3c04213" }	0
Please write the numbers and yields of the substrates containing a ferrocene structure	[ "2l contains a ferrocene structure, yield 98%", "2j contains a ferrocene structure, yield 92%", "2h contains a ferrocene structure, yield 91%", "2i contains a ferrocene structure, yield 92%" ]	1	{ "title": "Carboxylate-Catalyzed C-Silylation of Terminal Alkynes", "journal": "ORGANIC LETTERS", "doi": "10.1021/acs.orglett.3c04213", "url": "https://pubs.acs.org/doi/10.1021/acs.orglett.3c04213" }	0
What are the structural features of silane reagent 3? What role does it play in the reaction?	[ "Reagent 3 is an N,O-bis(trimethylsilyl) derivative (structure can be written as Me2N–Si(OSiMe3)Me), possessing one Si–N and one Si–O bond. Under TMAP activation it provides a TMS group, causing the terminal alkyne to be TMS-ified to give a silyl ether-protected alkyne.", "Reagent 3 is an N,O-bis(trimethylsilyl) ...	0	{ "title": "Carboxylate-Catalyzed C-Silylation of Terminal Alkynes", "journal": "ORGANIC LETTERS", "doi": "10.1021/acs.orglett.3c04213", "url": "https://pubs.acs.org/doi/10.1021/acs.orglett.3c04213" }	1
Which compounds shown in the figure have crystalline structures?	[ "The compounds that are clearly crystalline are 2v and 2x", "The compounds that are clearly crystalline are 2u and 2w", "The compounds that are clearly crystalline are 2w and 2x", "The compounds that are clearly crystalline are 2u and 2v" ]	0	{ "title": "Carboxylate-Catalyzed C-Silylation of Terminal Alkynes", "journal": "ORGANIC LETTERS", "doi": "10.1021/acs.orglett.3c04213", "url": "https://pubs.acs.org/doi/10.1021/acs.orglett.3c04213" }	0
Among the screening conditions, under which catalyst and reaction temperature is the selectivity for Δ⁹-THC(2) highest?	[ "When BF3·OEt2 is used at –10 °C for 3.5 h, the selectivity for Δ⁹-THC(2) is 85%.", "When AlCl3 is used at –10 °C for 15 min, the selectivity for Δ⁹-THC(2) is highest, reaching 87%.", "When TMSCl is used at room temperature for 48 h, the selectivity for Δ⁹-THC(2) is 83%.", "When BF3·OEt2 is used at 0 °C for 1...	1	{ "title": "Continuous-Flow Synthesis of Δ9-Tetrahydrocannabinol and Δ8-Tetrahydrocannabinol from Cannabidiol", "journal": "JOURNAL OF ORGANIC CHEMISTRY", "doi": "10.1021/acs.joc.3c00300", "url": "https://pubs.acs.org/doi/10.1021/acs.joc.3c00300" }	0
How many protic acids were screened in the figure?	[ "4", "8", "11", "14" ]	0	{ "title": "Continuous-Flow Synthesis of Δ9-Tetrahydrocannabinol and Δ8-Tetrahydrocannabinol from Cannabidiol", "journal": "JOURNAL OF ORGANIC CHEMISTRY", "doi": "10.1021/acs.joc.3c00300", "url": "https://pubs.acs.org/doi/10.1021/acs.joc.3c00300" }	0
Through which intermediates and reaction steps do Path A and Path B respectively give the products?	[ "Path A: Under acid catalysis, CBD is first protonated to generate an oxonium ion intermediate, then a cross-chain migration forms Δ⁸-THC(3), and finally cyclization yields Δ⁹-THC(2); Path B: Under acid treatment, CBD first cyclizes to form Δ⁸-iso-THC(4), which then isomerizes via a carbocation intermediate into Δ⁴...	1	{ "title": "Continuous-Flow Synthesis of Δ9-Tetrahydrocannabinol and Δ8-Tetrahydrocannabinol from Cannabidiol", "journal": "JOURNAL OF ORGANIC CHEMISTRY", "doi": "10.1021/acs.joc.3c00300", "url": "https://pubs.acs.org/doi/10.1021/acs.joc.3c00300" }	2
What is the reaction title shown in the table of this study?	[ "Batch screening of acid catalysts for the acid-catalyzed cyclization of CBD (1)", "Batch screening of acid catalysts for the base-catalyzed cyclization of CBD (1)", "Batch screening of acid catalysts for the acid-catalyzed cyclization of THC (2)", "Batch screening of acid catalysts for the acid-catalyzed oxi...	0	{ "title": "Continuous-Flow Synthesis of Δ9-Tetrahydrocannabinol and Δ8-Tetrahydrocannabinol from Cannabidiol", "journal": "JOURNAL OF ORGANIC CHEMISTRY", "doi": "10.1021/acs.joc.3c00300", "url": "https://pubs.acs.org/doi/10.1021/acs.joc.3c00300" }	0
Which acid, when added, gives the highest yield of 3?	[ "Chlorosulfonic acid", "TMSOTf", "Boron trifluoride etherate", "TFA" ]	1	{ "title": "Continuous-Flow Synthesis of Δ9-Tetrahydrocannabinol and Δ8-Tetrahydrocannabinol from Cannabidiol", "journal": "JOURNAL OF ORGANIC CHEMISTRY", "doi": "10.1021/acs.joc.3c00300", "url": "https://pubs.acs.org/doi/10.1021/acs.joc.3c00300" }	1
If the reaction system shifts from neutral to basic, what changes will occur in the photolysis mechanism of NDMA and the product distribution?	[ "Under basic conditions, the protonation degree of NDMA intermediates decreases, Paths A, Path B, Path C and Path D are suppressed, N–N cleavage more often enters the pathway (E) that reacts with O₂, increasing the generation of superoxide anion and peroxynitrate, promoting nitrate production. The yields of methyla...	0	{ "title": "An Organic Chemist's Guide to N-Nitrosamines: Their Structure, Reactivity, and Role as Contaminants", "journal": "JOURNAL OF ORGANIC CHEMISTRY", "doi": "10.1021/acs.joc.0c02774", "url": "https://pubs.acs.org/doi/10.1021/acs.joc.0c02774" }	3
Regarding the basic reaction process of Path A shown in the figure and its role in NDMA photolysis, which of the following statements is correct?	[ "In Path A, NDMA is excited by ultraviolet light to form an excited-state NDMA*, whose N–N bond cleaves to generate a nitrogen radical (N·) and a nitrosyl radical (NO·). The generated N· reacts with NDMA to form dimethylamine and an NDMA radical, the latter of which further fragments and hydrolyzes to produce NO2, ...	2	{ "title": "An Organic Chemist's Guide to N-Nitrosamines: Their Structure, Reactivity, and Role as Contaminants", "journal": "JOURNAL OF ORGANIC CHEMISTRY", "doi": "10.1021/acs.joc.0c02774", "url": "https://pubs.acs.org/doi/10.1021/acs.joc.0c02774" }	2
Under oxygen-rich conditions, which photolytic pathway is most favorable for the net degradation of NDMA? Please explain the reason.	[ "Under oxygen-rich conditions, Path A is most favorable for the net degradation of NDMA. Because O2 molecules in the excited state can rapidly capture NDMA* and oxidize it to generate NO·, subsequently producing superoxide anion (O2·–), which combines with NO· to form the unstable intermediate 33*, and finally hydr...	2	{ "title": "An Organic Chemist's Guide to N-Nitrosamines: Their Structure, Reactivity, and Role as Contaminants", "journal": "JOURNAL OF ORGANIC CHEMISTRY", "doi": "10.1021/acs.joc.0c02774", "url": "https://pubs.acs.org/doi/10.1021/acs.joc.0c02774" }	3
Which major radicals are involved in Path E shown in the figure, how do they interact with each other, and what oxygen-nitrogen compounds are ultimately formed?	[ "In Path E, the nitrosyl radical (NO·) reacts with oxygen to form the superoxide anion (O2·–), and the two combine to form peroxynitrite (ONOO–). ONOO– can reversibly convert to peroxynitrous acid (ONOOH) under protonation, and cleave to produce nitrate (NO3–), nitrogen dioxide (NO2) and nitric acid (HNO3). Meanwhi...	0	{ "title": "An Organic Chemist's Guide to N-Nitrosamines: Their Structure, Reactivity, and Role as Contaminants", "journal": "JOURNAL OF ORGANIC CHEMISTRY", "doi": "10.1021/acs.joc.0c02774", "url": "https://pubs.acs.org/doi/10.1021/acs.joc.0c02774" }	2
Which mechanistic pathways generate methylamine (MA)?	[ "Methylamine (MA, CH3NH2) mainly comes from the hydrolysis pathways of Path A and Path E.", "Methylamine (MA, CH3NH2) mainly comes from the hydrolysis pathways of Path A, Path D, and Path E.", "Methylamine (MA, CH3NH2) mainly comes from the hydrolysis pathways of Path D and Path E.", "Methylamine (MA, CH3NH2)...	1	{ "title": "An Organic Chemist's Guide to N-Nitrosamines: Their Structure, Reactivity, and Role as Contaminants", "journal": "JOURNAL OF ORGANIC CHEMISTRY", "doi": "10.1021/acs.joc.0c02774", "url": "https://pubs.acs.org/doi/10.1021/acs.joc.0c02774" }	2
How many bisphosphine ligands were screened in the figure?	[ "11", "6", "5", "8" ]	2	{ "title": "Palladium-Catalyzed Domino Aminocarbonylation of Alkynols: Direct and Selective Synthesis of Itaconimides", "journal": "JACS AU", "doi": "10.1021/jacsau.1c00221", "url": "https://pubs.acs.org/doi/10.1021/jacsau.1c00221" }	0
In ligand screening, which ligand gave the highest yield of 3aa? What is the ligand's type and the yield?	[ "Monophosphine ligand L11b (substituent Ad) performed best at 4.0 mol% loading, giving a yield of 3aa >99%.", "Monophosphine ligand L9 (substituent Cy) performed best at 4.0 mol% loading, giving a yield of 3aa of 15%.", "Bisphosphine ligand L3 performed best at 2.0 mol% loading, giving a yield of 3aa of 60%.", ...	0	{ "title": "Palladium-Catalyzed Domino Aminocarbonylation of Alkynols: Direct and Selective Synthesis of Itaconimides", "journal": "JACS AU", "doi": "10.1021/jacsau.1c00221", "url": "https://pubs.acs.org/doi/10.1021/jacsau.1c00221" }	0
Regarding the overall conversion process of this Pd-catalyzed aminocarbonylation reaction and the structural characteristics of the major product 3aa, which of the following statements is correct?	[ "The reaction uses 1-vinyl-1-cyclohexanol and 4-fluoroaniline as substrates, under 20 bar CO, 100 °C, catalyzed by the Pd(MeCN)2Cl2/ligand system, undergoes aminocarbonylation followed by intramolecular cyclization to give the N-aryl diketone heterocyclic product 3aa; this product consists of a cyclohexane framewor...	3	{ "title": "Palladium-Catalyzed Domino Aminocarbonylation of Alkynols: Direct and Selective Synthesis of Itaconimides", "journal": "JACS AU", "doi": "10.1021/jacsau.1c00221", "url": "https://pubs.acs.org/doi/10.1021/jacsau.1c00221" }	2
What are the catalyst, ligand, solvent, and the temperature and pressure conditions used in the reaction respectively?	[ "Catalyst is Pd(MeCN)2Cl2 (1.0 mol%); ligand is a bidentate phosphine (2.0 mol%) or a bulky monophosphine L (4.0 mol%); solvent is CH2Cl2 (2.0 mL); temperature 120 °C; CO pressure 40 psi; reaction time 20 h.", "Catalyst is Pd(MeCN)2Cl2 (1.0 mol%); ligand is a bidentate phosphine (2.0 mol%) or a bulky monophosphin...	3	{ "title": "Palladium-Catalyzed Domino Aminocarbonylation of Alkynols: Direct and Selective Synthesis of Itaconimides", "journal": "JACS AU", "doi": "10.1021/jacsau.1c00221", "url": "https://pubs.acs.org/doi/10.1021/jacsau.1c00221" }	0
Why can bulkier monophosphine ligands (such as L11b) significantly increase the yield of 3aa?	[ "Bulky monophosphine ligands increase the electron density of Pd, strengthening the Pd–CO bond and increasing CO adsorption, thereby promoting carbonyl insertion and increasing the yield of 3aa.", "Bulky monophosphine ligands occupy only one coordination site at the Pd center, leaving vacant sites favorable for a...	1	{ "title": "Palladium-Catalyzed Domino Aminocarbonylation of Alkynols: Direct and Selective Synthesis of Itaconimides", "journal": "JACS AU", "doi": "10.1021/jacsau.1c00221", "url": "https://pubs.acs.org/doi/10.1021/jacsau.1c00221" }	1

End of preview. Expand in Data Studio

RxnBench: A Benchmark for Chemical Reaction Figure Understanding

📘 Benchmark Summary

RxnBench (SF-QA) is a visual question answering (VQA) benchmark comprising 1,525 multiple-choice questions (MCQs) at the PhD-level of organic chemistry reaction understanding.

The benchmark is built from 305 scientific figures drawn from high-impact OpenAssess journals. For each figure, domain experts carefully designed five multiple-choice VQA questions targeting the interpretation of organic reaction diagrams. These questions were further refined through multiple rounds of rigorous review and revision to ensure both clarity and scientific accuracy. The questions cover a variety of types, including the description of chemical reaction images, extraction of reaction content, recognition of molecules or Markush structures, and determination of mechanisms. This benchmark challenges visual-language models on their foundational knowledge of organic chemistry, multimodal contextual reasoning, and chemical reasoning skills.

The benchmark is released in both English and Chinese versions.

📑 Task Types

We categorize chemical reaction visual question answering tasks into six types:

Type 0 — Fact Extraction: Direct retrieval of textual or numerical information from reaction schemes.
Type 1 — Reagent Roles and Functions Identification: Identification of reagents and their functional roles, requiring chemical knowledge and reaction-type awareness.
Type 2 — Reaction Mechanism and Process Understanding: Interpretation of reaction progression, including intermediates, catalytic cycles, and mechanistic steps.
Type 3 — Comparative Analysis and Reasoning: Comparative evaluation, causal explanation, or outcome prediction under varying conditions.
Type 4 — Multi-step Synthesis and Global Understanding: Comprehension of multi-step pathways, step-to-step coherence, and overall synthetic design.
Type 5 — Chemical Structure Recognition: Extraction and reasoning-based parsing of chemical structures in SMILES or E-SMILES (as defined in the MolParser paper).

🎯 Benchmark Evaluation

This benchmark evaluates model performance on multiple-choice question answering (MCQ) tasks.

We provide two versions of the prompt template, depending on the language setting.

English Prompt

Question: {question}
Choices:
A. {choice_A}
B. {choice_B}
C. {choice_C}
D. {choice_D}
Based on the image and the question, choose the most appropriate answer.
**Only output a single letter (A, B, C, or D)**. Do NOT output any other text or explanation.

Chinese Prompt

问题: {question}
选项:
A. {choice_A}
B. {choice_B}
C. {choice_C}
D. {choice_D}

请根据图像和问题，从以上四个选项中选择最合适的答案。
只输出单个字母 (A, B, C 或 D)，不要输出选项内容，也不要输出任何解释。

Evaluation Protocol

If the model’s output is not one of A, B, C, or D, we use GPT-4o to map the output to A–D based on the option content. The final evaluation reports the absolute accuracy of the benchmark in both English and Chinese versions.

Code Example: https://github.com/uni-parser/RxnBench

📊 Benchmark Leaderboard

We evaluated several of the latest popular MLLMs, including both closed-source and open-source models.

(continuously updated)

Moldel	Think	Weight	API-Version	RxnBench-En	RxnBench-Zh	Mean Score
Qwen3.5-397B-A17B	√	Open	-	0.9613	0.9639	0.9626
Gemini-3-Flash-preview	√	Proprietary	20251217	0.9593	0.9652	0.9623
Gemini-3.1-Pro-preview	√	Proprietary	20260219	0.9548	0.9666	0.9607
Qwen3.5-122B-A10B	√	Open	-	0.9528	0.9580	0.9554
Qwen3.5-27B	√	Open	-	0.9495	0.9593	0.9544
Seed2.0 Pro	√	Proprietary	20260215	0.9502	0.9561	0.9531
Qwen3.5-35B-A3B	√	Open	-	0.9456	0.9489	0.9472
Kimi K2.5	√	Open	-	0.9464	0.9462	0.9463
GPT-5.2(high)	√	Proprietary	20251211	0.9430	0.9462	0.9446
Seed1.8-Think	√	Proprietary	20251218	0.9325	0.9403	0.9364
Gemini-3-Pro-preview	√	Proprietary	20251119	0.9318	0.9403	0.9361
Qwen3.5-9B	√	Open	-	0.9298	0.9246	0.9272
GPT-5(high)	√	Proprietary	20250807	0.9279	0.9246	0.9263
Gemini-2.5-Pro	√	Proprietary	20250617	0.9095	0.9423	0.9259
GPT-5.1(high)	√	Proprietary	20251113	0.9213	0.9220	0.9216
GPT-5(medium)	√	Proprietary	20250807	0.9207	0.9226	0.9216
Qwen3-VL-235BA22B-Think	√	Open	-	0.9220	0.9134	0.9177
Qwen3-VL-32B-Think	√	Open	-	0.9128	0.9161	0.9144
GPT-5.1(medium)	√	Proprietary	20251113	0.9108	0.9141	0.9125
GPT-5-mini	√	Proprietary	20250807	0.9108	0.9128	0.9118
Qwen3.5-4B	√	Open	-	0.9056	0.9180	0.9118
Seed1.5-VL-Think	√	Proprietary	20250428	0.9056	0.9161	0.9109
GPT o3	√	Proprietary	20250416	0.9056	0.9115	0.9086
GPT o4 mini	√	Proprietary	20250416	0.9062	0.9075	0.9069
InternVL3.5-241B-A28B	√	Open	-	0.9003	0.9062	0.9033
Intern-S1	√	Open	-	0.8938	0.8944	0.8941
Qwen3-VL-30BA3B-Think	√	Open	-	0.8689	0.8590	0.8689
Step3-VL-10B	√	Open	-	0.8630	0.8597	0.8613
Qwen3-VL-Plus	×	Proprietary	20250923	0.8551	0.8656	0.8604
Qwen3-VL-8B-Think	√	Open	-	0.8636	0.8564	0.8600
Seed1.5-VL	×	Proprietary	20250328	0.8518	0.8669	0.8594
Qwen3-VL-235BA22B-Instruct	×	Open	-	0.8492	0.8675	0.8584
InternVL3-78b	×	Open	-	0.8531	0.8308	0.8420
Qwen3-VL-4B-Think	√	Open	-	0.8577	0.8256	0.8416
Intern-S1-mini	√	Open	-	0.8521	0.8282	0.8402
GLM-4.1V-9B-Thinking	√	Open	-	0.8392	0.8341	0.8367
Qwen3-VL-32B-Instruct	×	Open	-	0.8315	0.8407	0.8361
Qwen2.5-VL-72B	×	Open	-	0.8341	0.8308	0.8325
Qwen2.5-VL-Max	×	Proprietary	20250813	0.8192	0.8262	0.8227
GPT-5-nano	√	Proprietary	20250807	0.7980	0.7941	0.7961
Qwen2.5-VL-32B	×	Open	-	0.7980	0.7908	0.7944
Gemini-2.5-Flash	√	Proprietary	20250617	0.6925	0.8557	0.7741
Qwen3-VL-8B-Instruct	×	Open	-	0.7548	0.7495	0.7521
Qwen3-VL-30BA3B-Instruct	×	Open	-	0.7456	0.7436	0.7456
GPT-4o	×	Proprietary	20240806	0.7462	0.7436	0.7449
Qwen2.5-VL-7B	×	Open	-	0.7082	0.7233	0.7158
Qwen3-VL-4B-Instruct	×	Open	-	0.7023	0.7023	0.7023
Qwen3-VL-2B-Think	√	Open	-	0.6780	0.6708	0.6744
Qwen2.5-VL-3B	×	Open	-	0.6748	0.6643	0.6696
Qwen3.5-2B	√	Open	-	0.6597	0.6616	0.6607
GPT-4o mini	×	Proprietary	20240718	0.6636	0.6066	0.6351
Qwen3.5-0.8B	√	Open	-	0.6007	0.6066	0.6036
Qwen3-VL-2B-Instruct	×	Open	-	0.5711	0.5928	0.5820
Choice longest answer	-	-	-	0.4262	0.4525	0.4394
Deepseek-VL2	×	Open	-	0.4426	0.4216	0.4321
Random	-	-	-	0.2500	0.2500	0.2500

We also conducted separate evaluations for different task types (in RxnBench-en).

Moldel	Think	Weight	API-Version	Type0	Type1	Type2	Type3	Type4	Type5
Qwen3.5-397B-A17B	√	Open	-	0.9736	0.9722	0.9696	0.9769	0.9492	0.8507
Gemini-3-Flash-preview	√	Proprietary	20251217	0.9613	0.9643	0.9764	0.9630	0.9492	0.9030
Gemini-3.1-Pro-preview	√	Proprietary	20260219	0.9736	0.9524	0.9696	0.9583	0.9492	0.8433
Qwen3.5-122B-A10B	√	Open	-	0.9718	0.9563	0.9595	0.9583	0.9831	0.8284
Qwen3.5-27B	√	Open	-	0.9718	0.9722	0.9561	0.9630	0.9492	0.7761
Seed2.0 Pro	√	Proprietary	20260215	0.9560	0.9524	0.9628	0.9676	0.9322	0.8731
Qwen3.5-35B-A3B	√	Open	-	0.9683	0.9563	0.9595	0.9491	0.9661	0.7836
Kimi K2.5	√	Open	-	0.9542	0.9563	0.9561	0.9630	0.9661	0.8433
GPT-5.2(high)	√	Proprietary	20251211	0.9542	0.9643	0.9662	0.9491	0.9492	0.7910
Seed1.8-Think	√	Proprietary	20251218	0.9331	0.9484	0.9527	0.9444	0.9492	0.8284
Gemini-3-Pro-preview	√	Proprietary	20251119	0.9648	0.9246	0.9527	0.9398	0.9322	0.7463
Qwen3.5-9B	√	Open	-	0.9542	0.9444	0.9426	0.9398	0.9661	0.7388
GPT-5(high)	√	Proprietary	20250807	0.9313	0.9444	0.9527	0.9167	0.9661	0.8358
Gemini-2.5-Pro	√	Proprietary	20250617	0.9331	0.9246	0.9459	0.9491	0.9322	0.6343
GPT-5.1(high)	√	Proprietary	20251113	0.9243	0.9524	0.9426	0.9167	0.9661	0.7910
GPT-5(medium)	√	Proprietary	20250807	0.9349	0.9325	0.9493	0.9167	0.9492	0.7761
Qwen3-VL-235BA22B-Think	√	Open	-	0.9190	0.9405	0.9459	0.9213	0.9322	0.8433
Qwen3-VL-32B-Think	√	Open	-	0.9296	0.9405	0.9426	0.9259	0.9153	0.7015
GPT-5.1(medium)	√	Proprietary	20251113	0.9243	0.9365	0.9426	0.9167	0.9492	0.7090
GPT-5-mini	√	Proprietary	20250807	0.9225	0.9325	0.9257	0.9259	0.9831	0.7388
Qwen3.5-4B	√	Open	-	0.9366	0.9206	0.9257	0.9398	0.8983	0.6493
Seed1.5-VL-Think	√	Proprietary	20250428	0.8996	0.9365	0.9358	0.9074	0.9153	0.8060
GPT o3	√	Proprietary	20250416	0.9313	0.9325	0.9223	0.8981	0.9492	0.7090
GPT o4 mini	√	Proprietary	20250416	0.6391	0.7302	0.7500	0.6667	0.6271	0.4627
InternVL3.5-241B-A28B	√	Open	-	0.8944	0.9127	0.9291	0.9167	0.9153	0.8134
Intern-S1	√	Open	-	0.9014	0.9127	0.9223	0.9028	0.8814	0.7463
Qwen3-VL-30BA3B-Think	√	Open	-	0.8732	0.8810	0.9054	0.8843	0.9322	0.6940
Step3-VL-10B	√	Open	-	0.8926	0.8492	0.9054	0.8935	0.8983	0.6119
Qwen3-VL-Plus	×	Proprietary	20250923	0.8275	0.8968	0.8986	0.8565	0.9153	0.7687
Qwen3-VL-8B-Think	√	Open	-	0.8768	0.8730	0.8885	0.9028	0.8983	0.6567
Seed1.5-VL	×	Proprietary	20250328	0.9327	0.9127	0.9122	0.8472	0.8305	0.7015
Qwen3-VL-235BA22B-Instruct	×	Open	-	0.8204	0.8929	0.8986	0.8426	0.8814	0.7761
InternVL3-78b	×	Open	-	0.8556	0.8730	0.8885	0.8981	0.9153	0.6194
Qwen3-VL-4B-Think	√	Open	-	0.8838	0.8770	0.8615	0.9074	0.8983	0.6045
Intern-S1-mini	√	Open	-	0.8239	0.8690	0.8547	0.8611	0.8475	0.6791
GLM-4.1V-9B-Thinking	√	Open	-	0.8433	0.8690	0.8649	0.8657	0.8814	0.6493
Qwen3-VL-32B-Instruct	×	Open	-	0.8169	0.8571	0.8885	0.8519	0.8305	0.6866
Qwen2.5-VL-72B	×	Open	-	0.8063	0.8063	0.8770	0.9088	0.8102	0.9322
Qwen2.5-VL-Max	×	Proprietary	20250813	0.7958	0.8571	0.8885	0.8194	0.8983	0.6642
GPT-5-nano	√	Proprietary	20250807	0.8063	0.8452	0.8311	0.8241	0.7797	0.5672
Qwen2.5-VL-32B	×	Open	-	0.7729	0.8413	0.8750	0.8009	0.8305	0.6418
Gemini-2.5-Flash	√	Proprietary	20250617	0.7799	0.6111	0.6757	0.6620	0.7627	0.5373
Qwen3-VL-8B-Instruct	×	Open	-	0.7113	0.8175	0.8446	0.8241	0.7627	0.5075
Qwen3-VL-30BA3B-Instruct	×	Open	-	0.7042	0.7937	0.8311	0.7824	0.7119	0.5970
GPT-4o	×	Proprietary	20240806	0.7359	0.8175	0.7973	0.7500	0.7627	0.5224
Qwen2.5-VL-7B	×	Open	-	0.6678	0.7659	0.8041	0.7130	0.6441	0.5373
Qwen3-VL-4B-Instruct	×	Open	-	0.6708	0.7302	0.7804	0.7222	0.6610	0.5970
Qwen3-VL-2B-Think	√	Open	-	0.7342	0.6706	0.7128	0.7083	0.6102	0.3657
Qwen2.5-VL-3B	×	Open	-	0.6426	0.7381	0.7635	0.6898	0.6610	0.4776
Qwen3.5-2B	√	Open	-	0.6620	0.7103	0.7027	0.7083	0.6271	0.3955
GPT-4o mini	×	Proprietary	20240718	0.6391	0.7302	0.7500	0.6667	0.6271	0.4627
Qwen3.5-0.8B	√	Open	-	0.6215	0.6310	0.6486	0.6620	0.5254	0.2836
Qwen3-VL-2B-Instruct	×	Open	-	0.5405	0.6190	0.6318	0.6250	0.6102	0.3731
Deepseek-VL2	×	Open	-	0.4120	0.5040	0.4899	0.4907	0.3729	0.3060

We welcome pull requests with your model results.
Alternatively, if you would like to provide an API for evaluation, please contact fangxi@dp.tech

🆕 RxnBench-Doc

A single reaction image often lacks the information needed for full interpretation, requiring contextual text from the literature. Therefore, we also provide a benchmark for chemical reaction literature understanding.

https://huggingface.co/datasets/UniParser/RxnBench-Doc

📖 Citation

@article{li2025rxnbench,
  title={RxnBench: A Multimodal Benchmark for Evaluating Large Language Models on Chemical Reaction Understanding from Scientific Literature},
  author={Li, Hanzheng and Fang, Xi and Li, Yixuan and Huang, Chaozheng and Wang, Junjie and Wang, Xi and Bai, Hongzhe and Hao, Bojun and Lin, Shenyu and Liang, Huiqi and Zhang, Linfeng and Ke, Guolin},
  journal={arXiv preprint arXiv:2512.23565},
  year={2025}
}