Transfer of a positively charged acyl group between substituted phenolate ion nucleophiles: The Bronsted beta for the calibrating equilibrium for N-methylisonicotinyl (4-carbonyl-N-methylpyridinium) transfer

• Published in: J. Chem. Soc., Perkin Trans. 2 no. 11; pp. 2285 - 2291
• Main Authors: Colthurst, MJ, Nanni, M, Williams, A
• Format: Journal Article
• Language: English
• Published: CAMBRIDGE Royal Soc Chemistry 1996
• Subjects: Chemistry; Chemistry, Organic; Chemistry, Physical; Physical Sciences; Science & Technology; CATALYSIS; TRANSITION-STATE STRUCTURE; ACID; ESTERS; STRUCTURE-REACTIVITY CORRELATIONS; HYDROLYSIS; ACETYL GROUP TRANSFER; PARA-NITROPHENYL PICOLINATE

Rate constants have been measured for the reaction of substituted phenolate ions with aryl acetate esters and with aryl N-methylisonicotinate esters dagger. in aqueous solution. A new method is demonstrated for determining beta(eq) for group transfer from 4-nitrophenyl esters; it employs the rate co...