Variable trends in R-X bond dissociation energies (R = Me, Et, i-Pr, t-Bu)

被引：72
|
作者：
Coote, ML [1 ]
Pross, A
Radom, L
机构：
[1] Australian Natl Univ, Res Sch Chem, Canberra, ACT 0200, Australia
[2] Ben Gurion Univ Negev, Dept Chem, IL-84105 Beer Sheva, Israel
[3] Univ Sydney, Sch Chem, Sydney, NSW 2006, Australia
来源：
ORGANIC LETTERS | 2003年 / 5卷 / 24期
关键词：
D O I：
10.1021/ol035860+
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
High level ab initio molecular orbital calculations confirm experimental indications that the effect of alkyl substituents (R = Me, Et, j-Pr, t-Bu) on R-X bond dissociation energies varies considerably according to the nature of X. A simple qualitative explanation in terms of valence-bond theory is presented, highlighting the increasing importance of the stabilization of R-X by the ionic R+X- configuration for electronegative X substituents (such as F, OH, and OCH3).
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页码：4689 / 4692
页数：4
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