{"title":"2-肼基-1-甲基-1H-苯并[d]咪唑的原位有氧氧化：从量子化学角度洞察反应背景","authors":"Andrei V. Erkin, Viktor I. Krutikov","doi":"10.1016/j.cdc.2024.101161","DOIUrl":null,"url":null,"abstract":"<div><p>Herein, attempts at hydrazinolysis of 1-methyl-<em>1H</em>-benzo<em>[d]</em>imidazole-2-sulfonic acid <strong>6</strong> and its potassium salt <strong>9</strong> have been reported. None of them resulted in the isolation of 2-hydrazinyl-1-methyl-<em>1H</em>-benzo<em>[d]</em>imidazole <strong>3</strong>. Instead, 1-methyl-<em>1H</em>-benzo<em>[d]</em>imidazol-2(<em>3H</em>)-one <strong>10</strong> was obtained in some cases. The hydrazinolysis failure may be due to the aerobic oxidation of hydrazine <strong>3</strong> <em>in situ</em>. To get into the background for the reaction, the highest occupied molecular orbitals (HOMOs) of compound <strong>3</strong> and relatively oxidation-resistible 2-hydrazinyl-<em>1H</em>-benzo<em>[d]</em>imidazole <strong>11</strong> were comparatively considered. Based on the analysis of the regions of highest density of HOMOs in both hydrazines, the aminoguanidine moiety in compound <strong>3</strong> appeared to be more susceptible to oxidation as compared to the moiety in compound <strong>11</strong>.</p></div>","PeriodicalId":269,"journal":{"name":"Chemical Data Collections","volume":"53 ","pages":"Article 101161"},"PeriodicalIF":2.2180,"publicationDate":"2024-08-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Aerobic oxidation of 2-hydrazinyl-1-methyl-1H-benzo[d]imidazole in situ: A quantum chemical insight into the reaction background\",\"authors\":\"Andrei V. Erkin, Viktor I. Krutikov\",\"doi\":\"10.1016/j.cdc.2024.101161\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>Herein, attempts at hydrazinolysis of 1-methyl-<em>1H</em>-benzo<em>[d]</em>imidazole-2-sulfonic acid <strong>6</strong> and its potassium salt <strong>9</strong> have been reported. None of them resulted in the isolation of 2-hydrazinyl-1-methyl-<em>1H</em>-benzo<em>[d]</em>imidazole <strong>3</strong>. Instead, 1-methyl-<em>1H</em>-benzo<em>[d]</em>imidazol-2(<em>3H</em>)-one <strong>10</strong> was obtained in some cases. The hydrazinolysis failure may be due to the aerobic oxidation of hydrazine <strong>3</strong> <em>in situ</em>. To get into the background for the reaction, the highest occupied molecular orbitals (HOMOs) of compound <strong>3</strong> and relatively oxidation-resistible 2-hydrazinyl-<em>1H</em>-benzo<em>[d]</em>imidazole <strong>11</strong> were comparatively considered. Based on the analysis of the regions of highest density of HOMOs in both hydrazines, the aminoguanidine moiety in compound <strong>3</strong> appeared to be more susceptible to oxidation as compared to the moiety in compound <strong>11</strong>.</p></div>\",\"PeriodicalId\":269,\"journal\":{\"name\":\"Chemical Data Collections\",\"volume\":\"53 \",\"pages\":\"Article 101161\"},\"PeriodicalIF\":2.2180,\"publicationDate\":\"2024-08-26\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Chemical Data Collections\",\"FirstCategoryId\":\"1085\",\"ListUrlMain\":\"https://www.sciencedirect.com/science/article/pii/S2405830024000491\",\"RegionNum\":0,\"RegionCategory\":null,\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"Chemistry\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Chemical Data Collections","FirstCategoryId":"1085","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S2405830024000491","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"Chemistry","Score":null,"Total":0}
Aerobic oxidation of 2-hydrazinyl-1-methyl-1H-benzo[d]imidazole in situ: A quantum chemical insight into the reaction background
Herein, attempts at hydrazinolysis of 1-methyl-1H-benzo[d]imidazole-2-sulfonic acid 6 and its potassium salt 9 have been reported. None of them resulted in the isolation of 2-hydrazinyl-1-methyl-1H-benzo[d]imidazole 3. Instead, 1-methyl-1H-benzo[d]imidazol-2(3H)-one 10 was obtained in some cases. The hydrazinolysis failure may be due to the aerobic oxidation of hydrazine 3in situ. To get into the background for the reaction, the highest occupied molecular orbitals (HOMOs) of compound 3 and relatively oxidation-resistible 2-hydrazinyl-1H-benzo[d]imidazole 11 were comparatively considered. Based on the analysis of the regions of highest density of HOMOs in both hydrazines, the aminoguanidine moiety in compound 3 appeared to be more susceptible to oxidation as compared to the moiety in compound 11.
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Chemical Data Collections (CDC) provides a publication outlet for the increasing need to make research material and data easy to share and re-use. Publication of research data with CDC will allow scientists to: -Make their data easy to find and access -Benefit from the fast publication process -Contribute to proper data citation and attribution -Publish their intermediate and null/negative results -Receive recognition for the work that does not fit traditional article format. The research data will be published as ''data articles'' that support fast and easy submission and quick peer-review processes. Data articles introduced by CDC are short self-contained publications about research materials and data. They must provide the scientific context of the described work and contain the following elements: a title, list of authors (plus affiliations), abstract, keywords, graphical abstract, metadata table, main text and at least three references. The journal welcomes submissions focusing on (but not limited to) the following categories of research output: spectral data, syntheses, crystallographic data, computational simulations, molecular dynamics and models, physicochemical data, etc.
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