SOLUBILITY PREDICTIONS FOR SOLID NITRILES AND TERTIARY AMIDES BASED ON THE MOBILE ORDER THEORY

被引:23
作者
RUELLE, P
KESSELRING, UW
机构
[1] Institut d’Analyse Pharmaceutique, Ecole de Pharmacie, Université de Lausanne, Lausanne, CH-1015, BEP
关键词
SOLUBILITY; MOBILE ORDER THEORY; HYDROGEN BOND; STABILITY CONSTANT; THERMODYNAMICS; PROTON ACCEPTORS;
D O I
10.1023/A:1018990904867
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The solubilities of hexadecanenitrile, octadecanenitrile, N,N-diphenyl capramide, and N,N-diphenyl lauramide are predicted in common organic nonelectrolyte solvents using the solubility equation derived from the mobile order theory. In the framework of this theory, the formation of hydrogen bonds is treated on the basis of stability constants. Two values characterizing the nitrile-alcohol and the tertiary amide-alcohol hydrogen bonds, 175 and 600 cm(3) mol(-1), respectively, are determined. Although the formation of solute-solvent specific molecular interactions brings about a net increase in the solubility, the solubilities of the nitriles and amides in alcohols remain lower than those measured in nonassociated solvents because of the large negative hydrophobic effect of the alcohol molecules.
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页码:201 / 205
页数:5
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