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Attenuation of the Atmospheric Migration Ability of Polychlorinated Naphthalenes (PCN-2) Based on Three-dimensional QSAR Models with Full Factor Experimental Design

Gu, Wenwen, Chen, Ying, Li, Yu
Bulletin of environmental contamination and toxicology 2017 v.99 no.2 pp. 276-280
chemical elements, chlorinated naphthalenes, computer software, energy, experimental design, models, quantitative structure-activity relationships
Based on the experimental subcooled liquid vapor pressures (P L) of 17 polychlorinated naphthalene (PCN) congeners, one type of three-dimensional quantitative structure–activity relationship (3D-QSAR) models, comparative molecular similarity indices analysis (CoMSIA), was constructed with Sybyl software. Full factor experimental design was used to obtain the final regulation scheme for PCN, and then carry out modification of PCN-2 to significantly lower its P L. The contour maps of CoMSIA model showed that the migration ability of PCN decreases when the Cl atoms at the 2-, 3-, 4-, 5-, 6-, 7- and 8-positions of PCNs are replaced by electropositive groups. After modification of PCN-2, 12 types of new modified PCN-2 compounds were obtained with lnP L values two orders of magnitude lower than that of PCN-2. In addition, there are significant differences between the calculated total energies and energy gaps of the new modified compounds and those of PCN-2.