Kinetics and mechanism of decomposition of N-chloroamino acids. II: conformationally restricted models.

Abstract:

:The kinetics of decomposition of the following conformationally restricted N-chloro-alpha-amino acids were studied: 1-amino-1-cyclopentanecarboxylic acid (2), 1-amino-1-cyclohexanecarboxylic acid (4), 2-amino-2-norbornanecarboxylic acid (6), and 2-amino-2-benzonorbornanecarboxylic acid (8). The first-order rate constants obtained were 0.520, 5.197, 0.198, and 0.078, respectively, which correlated with the ring strain in the structurally related cyclic ketones cyclopentanone, cyclohexanone, norborane-2-one, and benzonorbornane-2-one. The data are supportive of a concerted mechanism for the decomposition reaction involving an imine-like transition state.

journal_name

J Pharm Sci

authors

Awad R,Hussain A,Crooks PA

doi

10.1002/jps.2600791216

subject

Has Abstract

pub_date

1990-12-01 00:00:00

pages

1121-2

issue

12

eissn

0022-3549

issn

1520-6017

pii

S0022-3549(15)48432-1

journal_volume

79

pub_type

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