Physical Sciences and Mathematics Commons^™

Kinetics And Mechanism Of Acylation Of Amines With 2-Naphthoyl Azide, Abraham L. Faburada

Dissertations

The reaction of 2-naphthoyl azide with primary and secondary amines in protic and aprotic solvents follows second-order kinetics. The effect of increasing solvent polarity is shown to increase the rate of reaction. For amines of similar basicity, the rate of reaction decreases with increasing steric hindrance on the amine. The changes in free energy and entropy of activation for n-butylamine and cyclohexylamine are in accord with steric requirements of amines. For amines of similar steric hindrance, the rate of reaction increases with increasing amine basicity. The mechanism of addition-elimination involving the formation of a tetrahedral intermediate is consistent with the …