Article

Appraisal of through-bond and through-space substituent effects via molecular electrostatic potential topography.

Computational Modeling and Simulation Section, National Institute for Interdisciplinary Science and Technology (CSIR), Trivandrum 695019, India.
The Journal of Physical Chemistry A (impact factor: 2.95). 11/2010; 114(46):12330-3. DOI:10.1021/jp107689z
Source: PubMed

ABSTRACT Through-bond (TB) and through-space (TS) substituent effects in substituted alkyl, alkenyl, and alkynyl arenes are quantified separately using molecular electrostatic potential (MESP) topographical analysis. The deepest MESP point over the aromatic ring (V(min)) is considered as a probe for monitoring these effects for a variety of substituents. In the case of substituted alkyl chains, the TS effect (79.6%) clearly dominates the TB effect, whereas in the unsaturated analogues the TB effect (∼55%) overrides the TS effect.

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Keywords

alkyl
 
alkyl chains
 
alkynyl arenes
 
aromatic ring
 
deepest MESP point
 
molecular electrostatic potential
 
Through-bond
 
through-space
 
unsaturated analogues