Steric Effects of Bridgehead Carbons Which Are α to Carbonyls

Authors

Howard D. Perlmutter, New Jersey Institute of Technology
David S. Kristol, New Jersey Institute of Technology
Reginald P.T. Tomkins, New Jersey Institute of Technology

Document Type

Article

Publication Date

1-1-1984

Abstract

The rates of alkaline hydrolysis of bi- and tricyclic bridgehead substituted esters varied inversely with the size of the bridge. Enthalpy and entropy of activation were found to be related to the flexibility of the systems. The kinetic results were compared with thermodynamic data and also with recent force-field calculations. It is suggested that base-catalyzed ester hydrolysis can be used to determine the effective size of alkyl substituents. © 1984, American Chemical Society. All rights reserved.

Identifier

0021230527 (Scopus)

Publication Title

Journal of the American Chemical Society

External Full Text Location

https://doi.org/10.1021/ja00314a015

e-ISSN

15205126

ISSN

00027863

First Page

340

Last Page

343

Issue

2

Volume

106

Recommended Citation

Perlmutter, Howard D.; Kristol, David S.; and Tomkins, Reginald P.T., "Steric Effects of Bridgehead Carbons Which Are α to Carbonyls" (1984). Faculty Publications. 21252.
https://digitalcommons.njit.edu/fac_pubs/21252