{"title":"Improving the stability of 2-phenyl-1,3-dimethyl imidazolium cations under alkaline conditions through various substitution strategies","authors":"Tiancheng Xiang, Hongyan Si","doi":"10.1007/s00214-024-03126-9","DOIUrl":null,"url":null,"abstract":"<p>The effects of various substituents at different substitution positions on the stability of imidazolium cations were investigated by studying the degradation reactions of several substituted 2-phenyl-1,3-dimethyl imidazolium cations (PDMIm<sup>+</sup>). The results of density functional theory calculations revealed that the stability of the imidazolium cation could be significantly enhanced by substitutions near the C2 position. These substitution positions included the ortho positions of the phenyl group and the N1/N3 and C4/C5 positions on the imidazole ring of PDMIm<sup>+</sup>. Moreover, the ethyl group was the most effective substituent among the ones discussed. The calculations also revealed that double alkyl substituents at ortho positions could more effectively improve the stability of imidazolium cations in the degradation reactions.</p>","PeriodicalId":1,"journal":{"name":"Accounts of Chemical Research","volume":null,"pages":null},"PeriodicalIF":16.4000,"publicationDate":"2024-06-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Accounts of Chemical Research","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1007/s00214-024-03126-9","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
引用次数: 0
Abstract
The effects of various substituents at different substitution positions on the stability of imidazolium cations were investigated by studying the degradation reactions of several substituted 2-phenyl-1,3-dimethyl imidazolium cations (PDMIm+). The results of density functional theory calculations revealed that the stability of the imidazolium cation could be significantly enhanced by substitutions near the C2 position. These substitution positions included the ortho positions of the phenyl group and the N1/N3 and C4/C5 positions on the imidazole ring of PDMIm+. Moreover, the ethyl group was the most effective substituent among the ones discussed. The calculations also revealed that double alkyl substituents at ortho positions could more effectively improve the stability of imidazolium cations in the degradation reactions.
期刊介绍：
Accounts of Chemical Research presents short, concise and critical articles offering easy-to-read overviews of basic research and applications in all areas of chemistry and biochemistry. These short reviews focus on research from the author’s own laboratory and are designed to teach the reader about a research project. In addition, Accounts of Chemical Research publishes commentaries that give an informed opinion on a current research problem. Special Issues online are devoted to a single topic of unusual activity and significance.
Accounts of Chemical Research replaces the traditional article abstract with an article "Conspectus." These entries synopsize the research affording the reader a closer look at the content and significance of an article. Through this provision of a more detailed description of the article contents, the Conspectus enhances the article's discoverability by search engines and the exposure for the research.
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