Molecular modeling analysis: “Why is 2-hydroxypyridine soluble in water but not 3-hydroxypyridine?”

被引：0

作者：

Fazlul Huq

Jun Qing Yu

机构：

[1] School of Biomedical Sciences,

[2] Faculty of Health Sciences,undefined

[3] C42,undefined

[4] The University of Sydney,undefined

[5] PO Box 170,undefined

[6] Lidcombe,undefined

[7] N.S.W. 1825,undefined

[8] Australia E-mail: f.huq@fhs.usyd.edu.au Phone: +61-2-9351-9522 Fax: +61-2-9351-9520,undefined

来源：

Molecular modeling annual | 2002年 / 8卷

关键词：

Keywords Hydroxypyridine; Energy of hydration; Solubility in water; Transplatinum; Planar; Amine;

D O I：

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中图分类号：

学科分类号：

摘要：

Molecular mechanics and semiempirical calculations using HyperChem 5 were carried out to investigate whether the results obtained can explain why 2-hydroxypyridine is far more soluble in water than 3-hydroxypyridine. The results of molecular mechanics calculations show that in solution in water the total energy of 2-hydroxypyridine in the oxo form is less than that of 3-hydroxypyridine in the zwitterionic form by 2.14 kcal mol–1. The difference is much greater for the AM1 optimized H-bonded molecules. The greater amount of energy released in dissolution and H-bond formation by 2-hydroxypyridine than by 3-hydroxypyridine together with a higher crystal lattice energy for the latter provide an explanation as to why 3-hydroxypyridine is much less soluble in water than 2-hydroxypyridine. When the predicted electronic spectral lines of the compounds were compared with the observed λmax values, it is found that generally the results obtained using AM1 agree more closely with the experimentally observed values.

引用

页码：81 / 86

页数：5