{"title":"Carbon-Fluorine Activation in the Gas Phase: The Reactions of Benzyl C-F Bonds and Silyl Cations.","authors":"Damon J Hinz, Allison E Krajewski, Jeehiun K Lee","doi":"10.1021/acs.joc.4c01775","DOIUrl":null,"url":null,"abstract":"<p><p>The activation of C-F bonds figures largely in both fundamental and applied chemical processes. Herein the activation of benzyl C-F bonds by silyl cations is examined both computationally and experimentally in the gas phase. The experimental rate constant values obtained herein have not heretofore been measured and provide insight into the intrinsic ability of silyl cations to activate C-F bonds. Trends in reactivity and correlations between theoretical and experimental data are discussed in the context of C-F bond cleavage.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":3.3000,"publicationDate":"2024-09-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"The Journal of Organic Chemistry","FirstCategoryId":"1","ListUrlMain":"https://doi.org/10.1021/acs.joc.4c01775","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2024/9/6 0:00:00","PubModel":"Epub","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
The activation of C-F bonds figures largely in both fundamental and applied chemical processes. Herein the activation of benzyl C-F bonds by silyl cations is examined both computationally and experimentally in the gas phase. The experimental rate constant values obtained herein have not heretofore been measured and provide insight into the intrinsic ability of silyl cations to activate C-F bonds. Trends in reactivity and correlations between theoretical and experimental data are discussed in the context of C-F bond cleavage.
期刊介绍:
The Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.