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

页码：427 / 431

页数：5

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