Kinetics and mechanism of decomposition of N-chloroamino acids. II: conformationally restricted models.
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.
Awad
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R
College of Pharmacy, University of Kentucky, Lexington 40536-0082.
Hussain
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A
Crooks
P A
PA
D000596:Amino Acids / Q000737:chemistry* / Q000493:pharmacokinetics*; D000598:Amino Acids, Cyclic; D003509:Cyclohexanecarboxylic Acids / Q000737:chemistry*; D003515:Cycloleucine / Q000737:chemistry*; D007700:Kinetics; D008956:Models, Chemical; D008968:Molecular Conformation; D013053:Spectrophotometry
D000596:Amino Acids; D000598:Amino Acids, Cyclic; D003509:Cyclohexanecarboxylic Acids; D003515:Cycloleucine; C006504:2-aminobicyclo(2,2,1)heptane-2-carboxylic acid