C-H Hyperconjugation in α-chlorocarbocations

Milan Mesić, Igor Novak, Dionis E. Sunko, Hrvoj Vančik

Research output: Contribution to journalArticlepeer-review

7 Citations (Scopus)


The lowering of Cβ-H stretching frequencies in carbocations 1a-d and 2a-c induced by hyperconjugation was tested as a possible probe for estimating the electron donating ability of α-substituents. Conclusions are based on the results of high level quantum chemical calculations confirmed with experimental FT-IR spectra. Because the decrease in the Cβ-H stretching frequency is comparable in 1b and in 1c, and in 2b and 2c respectively, it follows that α-substitution by a methyl group or by chlorine stabilizes a carbocation with almost the same effectiveness.

Original languageEnglish
Pages (from-to)2371-2374
Number of pages4
JournalJournal of the Chemical Society. Perkin Transactions 2
Issue number11
Publication statusPublished - Nov 1998


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