Atomic charge and density calculated by DFT method at twelve sites of biphenyl skeleton of polychlorinated biphenyls has been used to predict their bioconcentration factors. For prediction of bioconcentration factor, the 3D modeling and geometry optimization of all the compounds have been performed on workspace program of CAChe pro software of Fujitsu using the B88-PW91 GGA energy function with the DZVP basis set. Bioconcentration factor model, derived from partial atomic charges (r 2 = 0.917, r Asian Journal of Chemistry; Vol. 29, No. 11 (2017), 2515-2521 the DZVP basis set [41]. The values of descriptors, partial atom charges and HOMO densities at 12 sites of polychlorinated biphenyls, have directly been obtained from DFT calculation results. The Project Leader program associated with CAChe has been used for multiple linear regression (MLR) analysis [42] and various regression equations have been developed for prediction of bioconcentration factor (log BCFpre).
RESULTS AND DISCUSSIONThe general chemical structure of polychlorinated biphenyls [5] is based upon the biphenyl's skeleton, containing one to ten atoms of chlorine and has 12 sites viz. 1, 2, 3, 4, 5, 6, 1', 2', 3', 4', 5' and 6' (Fig. 1). Biphenyl is well known aromatic compound and like other aromatic compounds its characteristic reaction is also electrophilic substitution reactions. Biphenyl, on chlorination (Fe/Cl2) forms 4-chlorobiphenyl (∆HReaction = -28.865 kcal/mol, ∆GReaction = -27.61 kcal/mol and ∆SReaction = -6.839 cal/mol K) as major product with some 2-chlorobiphenyl (∆HReaction = -21.335 kcal/mol, ∆GReaction = -20.08 kcal/mol and ∆SReaction = -5.529 cal/mol K) as minor product. These on further chlorination give 4,4′-dichlorobiphenyl (∆HReaction = -28.238 kcal/mol, ∆GReaction = -25.728 kcal/mol and ∆SReaction = -9.741 cal/mol K) as major product and some 2,4′-dichlorobiphenyl (∆HReaction = -21.335 kcal/mol, ∆GReaction =