Calculated Double-Bond Stabilization by Bromine and Chlorine. Relevance to the kBr/kCl Element Effect

Shmaryahu Hoz, Harold Basch, Joel L. Wolk, Zvi Rappoport, Moshe Goldberg

Research output: Contribution to journalArticlepeer-review

10 Scopus citations

Abstract

The relative stabilization of a carbon-carbon double bond by CI and Br was obtained by ab initio MO calculations. The results at the MP2//RHF/CEP-21G* level corrected for differences in zero-point energy show that stabilization by Cll exceeds that by Br by ca. 1.3 kcal mol−1. Consequences related to the use of kBr/kCl ratios as mechanistic probes in vinylic substitution are discussed.

Original languageEnglish
Pages (from-to)5424-5426
Number of pages3
JournalJournal of Organic Chemistry
Volume56
Issue number18
DOIs
StatePublished - 1 Aug 1991

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