Premium
Efficient algorithm for quantitative assessment of similarities among atoms in molecules
Author(s) -
Cioslowski Jerzy,
Stefanov Boris B.,
Constans Pere
Publication year - 1996
Publication title -
journal of computational chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.907
H-Index - 188
eISSN - 1096-987X
pISSN - 0192-8651
DOI - 10.1002/(sici)1096-987x(199608)17:11<1352::aid-jcc8>3.0.co;2-l
Subject(s) - similarity (geometry) , molecule , steric effects , algorithm , orientation (vector space) , chemistry , computer science , mathematics , artificial intelligence , geometry , stereochemistry , image (mathematics) , organic chemistry
A new algorithm for quantitative assessment of similarity between two atoms in molecules is presented. Both the atomic similarity index and its derivatives with respect to the three Euler angles that describe the mutual orientation of the atoms under comparison are computed efficiently by taking advantage of the recently developed analytical representations for atomic zero‐flux surfaces. The use of such representations makes it possible to substantially enhance the accuracy of the computed similarity indices without increasing the cost of their evaluation. Numerical tests involving oxygen atoms in several carbonyl compounds demonstrate the ability of the new algorithm to discern small changes in atomic similarity that are brought about by second‐neighbor effects. Comparisons among hydrogen atoms in the acrolein molecule reveal the usefulness of the similarity index in detection and quantification of the effects of steric interactions on atomic shapes. © 1996 by John Wiley & Sons, Inc.