Author:
Bouab Otmane,Lamaty Gérard,Moreau Claude,Pomares Odile,Deslongchamps Pierre,Ruest Luc
Abstract
The rates of hydrolysis of orthoesters, 2,4,10-trioxaadamantanes, substituted in position 3 (R = H, CH3, C2H5, C6H5) have been determined at 25 and 40 °C in dioxane/water (60:40 by volume). Substitution of hydrogen by the groups CH3, C2H5, and C6H5 shows clearly a decrease in rate: 0.018 (CH3), 0.014 (C2H5), and 0.003 (C6H5). This decrease, in accord with substituent effects, plus the strongly negative entropies of activation observed, suggests that the rate-determining step is the addition of water to the carboxonium ion intermediate.
Publisher
Canadian Science Publishing
Subject
Organic Chemistry,General Chemistry,Catalysis
Cited by
27 articles.
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