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Nature of bonding in the sulfuryl group
Author(s) -
Chesnut D. B.,
Quin L. D.
Publication year - 2004
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/jcc.20003
Subject(s) - chemistry , covalent bond , bond order , delocalized electron , lone pair , bond dissociation energy , three center two electron bond , sextuple bond , molecule , sulfur , dissociation (chemistry) , computational chemistry , single bond , bent bond , bond length , group (periodic table) , organic chemistry
The SO sulfuryl bond in a number of representative sulfoxides and sulfones has been studied at the B3LYP/6‐311+G( d,p ) level in the atoms‐in‐molecules (AIM) approach involving the AIM delocalization index and the Cioslowski–Mixon localized orbitals and associated covalent bond order. The sulfuroxygen covalent bond is strongly polarized toward oxygen and the oxygen lone pairs provide significant backbonding to create short and strong SO bonds, similar in nature to those found in the analogous phosphoryl (PO) bond. Although the sulfoxides in general have larger delocalization indices than the sulfones, there is no correlation between these quantities and the bond dissociation energies. © 2004 Wiley Periodicals, Inc. J Comput Chem 25: 734–738, 2004