Journal of Pharmaceutical Sciences p. 1121 - 1122 (1990)
Update date:2022-08-10
Topics:
Awad
Hussain
Crooks
The kinetics of decomposition of the following conformationally restricted N-chloro-α-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.
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