Enhanced α-CH Acidity and Reactivity of Lewis Acid-Base Complexes in the Gas Phase
Document Type
Article
Publication Title
Angewandte Chemie International Edition
Department
Chemistry
ISSN
1433-7851
Volume
36
Issue
20
DOI
10.1002/anie.199722301
First Page
2230
Last Page
2232
Publication Date
11-3-1997
Abstract
Borane complexation at the heteroatom increases the gas‐phase C-H acidities of dimethyl sulfide, trimethylamine, and trimethylphosphane by up to 20 kcal mol−1. Deprotonation of the volatile Lewis acid–base complexes in the gas phase produces dipole‐stabilized carbanions that do not rearrange to the more stable borate isomers. The complexation also enhances the reactivity of pendant methyl and ethyl groups toward substitution and elimination reactions.
Recommended Citation
Ren, J.,
Workman, D. B.,
&
Squires, R. R.
(1997).
Enhanced α-CH Acidity and Reactivity of Lewis Acid-Base Complexes in the Gas Phase.
Angewandte Chemie International Edition, 36(20), 2230–2232.
DOI: 10.1002/anie.199722301
https://scholarlycommons.pacific.edu/cop-facarticles/660