Abstract
Rates and thermodynamic activation parameters have been determined for the water-catalyzed hydrolysis of 1-benzoyl-3-phenyl-1,2,4-triazole ( 1) in aqueous solutions containing 1:1 copolymers of maleic acid with ethyl vinyl ether (MAc-EVE), ethyl vinyl ether/ n-butyl vinyl ether (1:1) (MAc-EVE-nBVE), n-butyl vinyl ether (MAc- nBVE), 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- nBVE 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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