α-C-H bond dissociation energies of some tertiary amines

被引：70
|
作者：
Dombrowski, GW
Dinnocenzo, JP
Farid, S
Goodman, JL
Gould, IR
机构：
[1] Univ Rochester, Ctr Photoinduced Charge Transfer, Rochester, NY 14627 USA
[2] Univ Rochester, Dept Chem, Rochester, NY 14627 USA
[3] Eastman Kodak Co, Res Labs, Rochester, NY 14650 USA
来源：
JOURNAL OF ORGANIC CHEMISTRY | 1999年 / 64卷 / 02期
关键词：
D O I：
10.1021/jo9813843
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The alpha-C-H bond dissociation energies of 14 tertiary, trialkyl- and arylalkylamines have been measured by photoacoustic calorimetry (PAC). In general, the data lead to an upward revision of the bond dissociation energies (BDE's). The effects of alpha-phenyl and alpha-vinyl substitution have been quantified for the first time. alpha-Phenyl substitution was found to have a significantly smaller effect on lowering alpha-C-H BDE's than alpha-vinyl substitution. These data provide a thermochemical confirmation of the stereoelectronic hypothesis proposed by Lewis et al. in 1982.
引用
收藏
页码：427 / 431
页数：5
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