The influence of micellization ofn-decylamine on its basicity and reactivity toward carboxylic acid esters |
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Authors: | A. B. Mirgorodskaya L. A. Kudryavtseva B. E. Ivanov |
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Affiliation: | (1) A. E. Arbuzov Institute of Organic and Physical Chemistry, Kazan' Scientific Center of the Russian Academy of Sciences, 8 ul. Akad. ArbuZova, 420083 Kazan', Russian Federation |
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Abstract: | Micellization ofn-decylamine in aqueous solution leads to substantial decrease in its pKa, and increase in its reactivity in the nucleophilic substitution ofp-nitrophenylic esters of carboxylic acids (up to 70 times compared to ethylamine which forms no micelles). The influence of cetylpyridinium bromide on the acid-base properties ofn-decylamine and its reactivity was investigated. It was found that the reaction withn-decylamine can be accelerated or retarded depending on the hydrophobicity of the esters. The quantitative characteristics of the mieellar catalytic processes were estimated.Translated fromIzvestiya Akademii Nauk Seriya Khimicheskaya, No. 2, pp. 366–370, February, 1996. |
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Keywords: | n-decylamine esters of carboxylic acids cetylpyridinium bromide micelhzation basicity nucleophilic substitution |
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