Appraisal of through-bond and through-space substituent effects via molecular electrostatic potential topography.
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.
Computational Modeling and Simulation Section, National Institute for Interdisciplinary Science and Technology (CSIR), Trivandrum 695019, India.
Fareed Bhasha
FB
Sayyed
Cherumuttathu H
CH
Suresh
Shridhar R
SR
Gadre
D006841:Hydrocarbons, Aromatic / Q000737:chemistry* / Q000378:metabolism*; D008956:Models, Chemical; D015394:Molecular Structure; D055672:Static Electricity
D006841:Hydrocarbons, Aromatic