3D weighting of molecular descriptors for QSPR/QSAR by the method of ideal symmetry (MIS). 1. Application to boiling points of alkanes

Andrey Toropov, Alla Toropova, Temur Ismailov, Danail Bonchev

Research output: Contribution to journalArticle

Abstract

The method of ideal symmetry (MIS), developed recently, presents molecules as systems of mutually repulsing atoms connected by covalent bonds of constant length. In this paper we have used MIS optimized geometry to define a vertex 3D weight as a metric analogue of the vertex distance sum in molecular graphs. These 3D weights were used as a substitute for the vertex degrees in several well known topological (2D) indices, thus producing a series of 3D-weighted molecular descriptors. The novel indices were tested in calculating the boiling points of a series of 73 C3-C9 alkanes and showed generally a better performance than the original 2D indices. The best 1-, 2-, and 3-variable linear regression models incorporated 3D zero-order molecular connectivity with correlation coefficients of 0.9892, 0.9961, and 0.9986, and standard deviations of 5.97, 3.64, and 2.17°C, respectively. The approach was further validated by correlations with four other properties of alkanes (heats of formation, heats of vaporization, heats of atomization, and molar volume). The potential of the proposed 3D weighting of topological indices for QSPR/QSAR studies was thus demonstrated.

Original languageEnglish
Pages (from-to)237-247
Number of pages11
JournalJournal of Molecular Structure: THEOCHEM
Volume424
Issue number3
Publication statusPublished - Feb 18 1998

Keywords

  • 3D atomic weights
  • 3D molecular descriptors
  • Alkane properties
  • Method of ideal symmetry
  • QSPR

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Computational Theory and Mathematics
  • Atomic and Molecular Physics, and Optics

Fingerprint Dive into the research topics of '3D weighting of molecular descriptors for QSPR/QSAR by the method of ideal symmetry (MIS). 1. Application to boiling points of alkanes'. Together they form a unique fingerprint.

  • Cite this