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http://dx.doi.org/10.5012/bkcs.2009.30.4.787

Prediction of Hydroxyl Substitution Site(s) of Phenol, Monochlorophenols and 4-Chloronitrobenzene by Atomic Charge Distribution Calculations  

Lee, Byung-Dae (Division of Health, Uiduk University)
Lee, Min-Joo (Department of Chemistry, Changwon National University)
Publication Information
Bulletin of the Korean Chemical Society / v.30, no.4, 2009 , pp. 787-790 More about this Journal
Abstract
The predictions of the radical reaction sites for phenol, 2-, 3- and 4-chlorophenols (CPs) and 4-chloronitrobenzene (CNB) were studied by atomic charge distribution calculations. The atomic charge distributions on each atom of these molecules were obtained using the CHelpG and MK (Merz-Kollman/Singh) methods with the optimized structural parameters determined by DFT calculation at the level of BLYP/6-311++G(d,p). By comparing the experimentally obtained hydroxyl addition site(s) and the calculated atomic charges on carbon atoms of phenol and CPs, we found that hydroxyl substitution by oxidation reaction mainly occurred to the carbon(s) with high atomic charges. With these results, we were easily able to predict the position(s) of the ·OH reaction site(s) of phenol, CPs and CNB through atomic charge distribution calculations.
Keywords
Atomic charge distribution; CHelpG; MK; Hydroxyl radical reaction;
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