脂肪胺类化合物脂水分配系数的QSPR研究(英文)

QSPR study on octanol-water partition coefficient(lgK_(OW)) of aliphatic amine

用16种脂肪胺类化合物HF/6-31G^(**),HF/6-311G^(**),DFT-B3LYP/6-31G^(**)和DFT-B3LYP/6-311G^(**)全优化计算结构参数:分子最高占用和最低空轨道能(E_(HOMO)和E_(LUMO)),分子次最高占用和次最低空轨道能(E_(NHOMO)和E_(NLUMO)),分子总能量(E_T),氢原子所带的最高正电荷(q_H^+),最负原子的静电荷(q^-),分子偶极矩(μ)和分子体积(V),对它们的脂水分配系数(lgK_(OW))分别进行定量构效关系(QSPR)研究。结果表明:脂肪胺的lgK_(OW)与分子最低空轨道能(E_(LUMO)),分子的总能量(E_T)和分子偶极距(μ)的相关性较好,成功地建立了lgK_(OW)的QSPR方程。特别是基于B3LYP/6-311G^(**)基组建立的方程具有更好的预测能力,并通过VIF值和t值对其稳健性进行了检验,结果良好。

The Hartree-Fock（HF） and DFT-B3LYP methods, with the basis sets 6-31G^＊＊ and 6-311G^＊＊, were employed to calculate the molecular geometries and electronic structures of 16 aliphatic amine compounds. EHOMO, ELUMO, ENHOMO, ENLUMO, ET, QH, Q, μ and V were selected as structural descriptors. The experimental data of octanol-water partition coefficient （IgKow） along with the above nine structural parameters, was used to establish the quantitative structure-activity relationships （QSAR）. The results indicate that there is a good multiple linear relationship between experimental value of lgKow and energy of the lowest unoccupied molecular orbital （ELUMO）, the total energy of the molecular （ET） and dipole moments （u）. Especially, lgKow dependent equation calculated at the B3LYP/6-311G^＊＊ level is more advantageous than others in view of their correlation and predictive abilities. This dependent equation was validated by variance inflation factors （V/F） and t-test methods.