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4567698 
Journal Article 
Are amines basic or nucleophilic catalysts for oxirane ring opening by proton-donating nucleophiles? 
Bakhtin, SG; Shved, EN; Bespal'ko, YuN 
2016 
1 
Kinetics and Catalysis
ISSN: 0023-1584
EISSN: 1608-3210 
57 
1 
47-51 
WOS:000373228300007 
The behavior of amines as catalysts for oxirane acidolysis and phenolysis has been studied using kinetic methods. The apparent catalytic and noncatalytic reaction rate constants have been estimated. It has been demonstrated that the noncatalytic pathway has almost no effect on the apparent reaction rate constant. In order to determine the character of the behavior of amines (bases/nucleophiles) in this reaction, their reactivity has been analyzed within the conceptions of basic and nucleophilic mechanisms of catalysis. Based on the quantitative amine structure-catalytic activity correlation, it has been shown by comparing the values of correlation coefficients (r) of equations describing mechanisms for various reaction systems that, in the reactions of oxiranes with proton donors (carboxylic acids and phenols), the catalytic activity of tertiary amines/pyridines is determined by their nucleophilicity rather than basicity. 
amines; basic catalysts; nucleophilic catalysts; oxirane ring opening; proton-donating nucleophiles