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

Access to Document

10.1021/jo00018a042

Cite this

@article{0f063b7525e4473b9190e7351ab4a1cb,

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

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.",

author = "Shmaryahu Hoz and Harold Basch and Wolk, {Joel L.} and Zvi Rappoport and Moshe Goldberg",

year = "1991",

month = aug,

day = "1",

doi = "10.1021/jo00018a042",

language = "אנגלית",

volume = "56",

pages = "5424--5426",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "18",

}

TY - JOUR

T1 - Calculated Double-Bond Stabilization by Bromine and Chlorine. Relevance to the kBr/kCl Element Effect

AU - Hoz, Shmaryahu

AU - Basch, Harold

AU - Wolk, Joel L.

AU - Rappoport, Zvi

AU - Goldberg, Moshe

PY - 1991/8/1

Y1 - 1991/8/1

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.

UR - http://www.scopus.com/inward/record.url?scp=0000697295&partnerID=8YFLogxK

U2 - 10.1021/jo00018a042

DO - 10.1021/jo00018a042

M3 - ???researchoutput.researchoutputtypes.contributiontojournal.article???

AN - SCOPUS:0000697295

SN - 0022-3263

VL - 56

SP - 5424

EP - 5426

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 18

ER -

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

Abstract

Access to Document

Other files and links

Fingerprint

Cite this