Carbocations

Chapter 5 Carbocations V. M. Moreira, V. M. Moreira Laboratory of Pharmaceutical Chemistry, Faculty of Pharmacy, University of Coimbra, Portugal Centre for Neuroscience and Cell Biology, University of Coimbra, Portugal Centre for Innovative Biomedicine and Biotechnology, University of Coimbra, PortugalSearch for more papers by this author V. M. Moreira, V. M. Moreira Laboratory of Pharmaceutical Chemistry, Faculty of Pharmacy, University of Coimbra, Portugal Centre for Neuroscience and Cell Biology, University of Coimbra, Portugal Centre for Innovative Biomedicine and Biotechnology, University of Coimbra, PortugalSearch for more papers by this author Book Editor(s):Mark Moloney, Mark Moloney University of Oxford, Mansfield Road, Oxford, UK, OX1 3TA United KingdomSearch for more papers by this author First published: 15 March 2024 https://doi.org/10.1002/9781119716846.ch5Book Series:Organic Reaction Mechanisms Series AboutPDFPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShareShare a linkShare onEmailFacebookTwitterLinkedInRedditWechat Summary A density-functional theory study of the reaction of butadiene with the allyl cation, in the gas phase and dimethyl sulfoxide, has brought to focus the fact that the widths of pathways to competing products in a reaction may be more relevant for determining the selectivity than barrier heights. The intermediacy of carbocations in studies including zeolites continued to be a topic of interest. The reactivity of the benzyl carbocation with benzene as a weak base was studied by quantitative infrared spectroscopy. The interconversion of cyclopropylcarbinyl and cyclobutyl cations is revisited using the concept of conformational landscape. The observation of the model hydrogen migration in carbocations using molecular dynamics calculations suggested that hydrogen migration velocity decreases with stronger electrostatic interactions between the hydrogen and neighbouring groups (drag concept) and that this property may be exploited for rationalizing previous experimental results and designing novel reactions. References Frontier , A. J. and Hernandez , J. J. , Acc. Chem. Res. , 53 , 1822 ( 2020 ). 10.1021/acs.accounts.0c00284 CASPubMedWeb of Science®Google Scholar Tsuji , H. and Kawatsura , M. , Asian J. Org. 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