Quantitative structure-property relationship study of normal boiling points for halogen/oxygen/sulfur-containing organic compounds using the CODESSA program

QSPR (Quantitative Structure-Property Relationship) models for the estimation of boiling points of organic compounds containing halogens, oxygen, or sulfur without hydrogen bonding were established with the CODESSA (Comprehensive Descriptors for Structural and Statistical Analysis) program developed by Katritzky and coworkers. The boiling points of 185 compounds containing oxygen or sulfur can be accurately computed with a MLR (Multi-Linear Regression) equation containing six theoretical descriptors and having the following statistical indices: r = 0.992 and s = 6.3 degrees C. For a set of 534 halogenated alkanes C-1 - C-4 the best MLR equation with five descriptors has r = 0.990 and s = 9.0 degrees C. For subsets of molecules corresponding to monoethers, monosulfides, F- and Cl-containing compounds or F-containing compounds, even better MLR models were obtained showing that a greater accuracy can be obtained for the estimation of boiling points with QSPR models developed for restricted classes of compounds. The QSPR models developed with CODESSA allow accurate computation of the boiling points of organic compounds using simple constitutional, topological, electrostatic and quantum indices that can be computed with standard quantum chemistry packages. (C) 1998 Elsevier Science Ltd. All rights reserved.