Substituent effects in the addition of carboxylic acids to arylcarbodiimides

WL Mock, KJ Ochwat

Index: Mock, William L.; Ochwat, Krzysztof J. Journal of the Chemical Society. Perkin Transactions 2, 2002 , # 4 p. 843 - 847

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Abstract

Rates of addition in aqueous solution of RCOOH (R= CH3–, CH3OCH2–, ClCH2–, Cl2CH–) to ArNCNCH2CH2CH2N+ (CH3) 3 [Ar= C6H5–, 3-ClC6H4–, 4-CH3OC6H4–, 3, 4-Cl2C6H3– , 2, 4-(CH3O) 2C6H3–] yielding a transient O-acylisourea, have been measured as a function of pH. Relative activities indicate a reaction mechanism in which a carboxylate anion adds to a mono-or di-protonated arylcarbodiimide, available in minor amounts. Only ...