QSPR Modeling using Catalan Solvent and Solute Parameters

Journal of the Brazilian Chemical Society

Tabriz University of Medical Sciences, Tabriz, Iran¹  Ghafourian, Taravat¹  Shayanfar, Ali¹  Tabriz University of Medical Sciences, Iran¹  Universities of Kent and Greenwich, United Kingdom¹  Kimia Research Institute, Tabriz, Iran¹  Jouyban, Abolghasem¹  Fakhree, Mohammad A. A.¹ 

关键词: Catalan;    solvatochromic;    solubility;    modeling;    QSPR;   

DOI  :  10.1590/S0103-50532011000400011

学科分类：化学（综合）

来源: SciELO

【 摘 要 】

The field of quantitative structure-property relationship (QSPR) can greatly benefit from molecular descriptors that particularly represent the intermolecular interactions. Catalan has developed a set of solvatochromic scales for solvents, which could be exploited for this purpose. In this work, Catalan solvent scales were explored as molecular descriptors for the development of QSPR models, and for the calculation of new solute descriptors for further use in QSPR. Catalan solvent scales and the newly derived solute descriptors were compared with the commonly used set of Abraham descriptors in terms of the quality of the developed QSPRs. Catalan solvent parameters, which showed modest correlation with the corresponding Abraham descriptors, proved to be successful in modeling melting point, boiling point, flash point, refractive index, surface tension, density, and solubility parameter of the solvents with geometric mean relative deviations (GMRD) of 7.1, 6.6, 4.9, 3.8, 9.1, 6.0, and 4.2%, respectively. The solute descriptors were obtained from regression equations between a solute's solubility in different solvents with an overall GMRD of 30.0%. The solute descriptors obtained in this way outperformed Abraham general solvation model in the calculation of aqueous solubility for 27 solutes of broad chemical ranges. It was concluded that Catalan descriptors can be regarded as a valuable resource for QSPR modeling.

【 授权许可】

Unknown