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

doi:10.1021/jo00018a042

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

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

Department of Chemistry

Research output: Contribution to journal › Article › peer-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 k_Br/k_Cl ratios as mechanistic probes in vinylic substitution are discussed.

Original language	English
Pages (from-to)	5424-5426
Number of pages	3
Journal	Journal of Organic Chemistry
Volume	56
Issue number	18
DOIs	https://doi.org/10.1021/jo00018a042
State	Published - 1 Aug 1991

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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.",

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AU - Hoz, Shmaryahu

AU - Basch, Harold

AU - Wolk, Joel L.

AU - Rappoport, Zvi

AU - Goldberg, Moshe

PY - 1991/8/1

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N2 - 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.

AB - 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.

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

Abstract

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