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Neutral hydrolysis of 1-benzoyl-3-phenyl-1,2,4-triazole in the presence of copolymers of maleic acid with alkyl vinyl ethers. The effect of hydrophobic microdomains

✍ Scribed by Albert Jan De Groot; Jan Jager; Jan B.F.N. Engberts


Publisher
Elsevier Science
Year
1988
Tongue
English
Weight
346 KB
Volume
24
Category
Article
ISSN
0014-3057

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✦ Synopsis


Rates and thermodynamic activation parameters have been determined for the watercatalyzed hydrolysis of l-benzoyl-3-phenyl-l,2,4-triazole (1) in aqueous solutions containing l:l copolymers of maleic acid with ethyl vinyl ether (MAc-EVE), ethyl vinyl ether/n-butyl vinyl ether (l:l) (MAc-EVE-nBVE), n-butyl vinyl ether (MAc-n BVE), and n-hexyl vinyl ether (MAc-nHVE). Substantial retardations are found in the presence of MAc-nBVE and MAc-nHVE and a modest inhibition in solutions containing MAc-EVE-n BVE but MAc-EVE hardly affects the hydrolysis of 1. The inhibitions are interpreted in terms of hydrophobic binding of 1 to the compact conformation of the unionized copolymer and subsequent hydrolysis at relatively "dry" binding sites in the hydrophobic microdomains. An increase of the degree of ionization of MAc-nBVE and MAc-nHVE ultimately leads to a conformational transition to an extended coil and a concomitant decrease of the retardation.


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