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

G. W. Dombrowski, J. P. Dinnocenzo, S. Farid, J. L. Goodman, Ian Gould

Research output: Contribution to journalArticle

69 Citations (Scopus)

Abstract

The α-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 α-phenyl and α-vinyl substitution have been quantified for the first time. α-Phenyl substitution was found to have a significantly smaller effect on lowering α-C-H BDE's than α-vinyl substitution. These data provide a thermochemical confirmation of the stereoelectronic hypothesis proposed by Lewis et al. in 1982.

Original languageEnglish (US)
Pages (from-to)427-431
Number of pages5
JournalJournal of Organic Chemistry
Volume64
Issue number2
DOIs
StatePublished - Jan 22 1999
Externally publishedYes

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Amines
Substitution reactions
Photoacoustic effect
Calorimetry

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Dombrowski, G. W., Dinnocenzo, J. P., Farid, S., Goodman, J. L., & Gould, I. (1999). α-C-H bond dissociation energies of some tertiary amines. Journal of Organic Chemistry, 64(2), 427-431. https://doi.org/10.1021/jo9813843

α-C-H bond dissociation energies of some tertiary amines. / Dombrowski, G. W.; Dinnocenzo, J. P.; Farid, S.; Goodman, J. L.; Gould, Ian.

In: Journal of Organic Chemistry, Vol. 64, No. 2, 22.01.1999, p. 427-431.

Research output: Contribution to journalArticle

Dombrowski, GW, Dinnocenzo, JP, Farid, S, Goodman, JL & Gould, I 1999, 'α-C-H bond dissociation energies of some tertiary amines', Journal of Organic Chemistry, vol. 64, no. 2, pp. 427-431. https://doi.org/10.1021/jo9813843
Dombrowski, G. W. ; Dinnocenzo, J. P. ; Farid, S. ; Goodman, J. L. ; Gould, Ian. / α-C-H bond dissociation energies of some tertiary amines. In: Journal of Organic Chemistry. 1999 ; Vol. 64, No. 2. pp. 427-431.
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