2D and 3D quantitative structure-biodegradability relationship study of phenol derivatives

Abstract

Based on the experimental data of production of carbon dioxide (PCD) of phenol derivatives, a 2D-QSBR model was established between PCD and quantum chemistry parameters on phenol derivatives which were calculated at B3LYP/6-311G** level. The 2D-QSBR model contains two variables: molecular average polarizability ( α ) and standard entropy ( S Θ). α has greater effect on PCD than SΘ. The correlation coefficients ( R 2) and cross-validation correlation coefficients ( q 2) of the 2D-QSBR model at B3LYP/6-311G** level are 0.933 and 0.894, respectively, showing the priority of this model over models based on midix and 6-31G* level. Correspondingly, a 3D-QSBR model was also established using comparative molecular similarity index analysis (CoMSIA). The R 2 and q 2 of CoMSIA model are 0.964 and 0.716, respectively. The 3D contour maps suggested that the H-bonding donor and H-bonding acceptor factors have greater impact on PCD, and hydrophobic factors also have significant effect on PCD. The result indicates that the 2D-QSBR and 3D-QSBR models have strong stability and good predictability.