The comparative study of linear solvatation energy relationship for the reactivity of pyridine carboxylic acids with diazodiphenylmethane in protic and aprotic solvents

Abstract

Protic and aprotic solvent effects on the reactivity of picolinic, nicotinic and isonicotinic acid, as well as of some substituted nicotinic acids with diazodiphenylmethane (DDM) were investigated. In order to explain the kinetic results through solvent effects, the second-order rate constants for the reaction of the examined acids with DDM were correlated using the Kamlet-Taft solvatochromic equation. The correlations of the kinetic data were carried out by means of the multiple linear regression analysis and the solvent effects on the reaction rates were analyzed in terms of the contributions of the initial and the transition state. The signs of the equation coefficients support the already known reaction mechanism. The solvatation models for all the investigated acids are suggested and related to their specific structure.

Keywords

• pyridine carboxylic acids
• linear solvatation energy relationship
• diazodiphenylmethane
• protic and aprotic solvents