Prediction of 1-octanol-water and air-water partition coefficients for nitro-aromatic compounds from molecular dynamics simulations
Prediction of 1-octanol-water and air-water partition coefficients for nitro-aromatic compounds from molecular dynamics simulations
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DOI：
10.1039/c3cp44284e
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发表时间：
2013-01-01
影响因子：
3.3
通讯作者：
Potoff, Jeffrey J.
中科院分区：
文献类型：
--
作者：
Bhatnagar, Navendu;Kamath, Ganesh;Potoff, Jeffrey J.
基于相平衡转移势（TraPPE），建立了12种硝基芳烃化合物的联合原子力场，包括2，4-二硝基甲苯（2，4-DNT），2，6-二硝基甲苯（2，6-DNT），3-硝基甲苯（3-NT），4-硝基甲苯（4-NT），1，3-二硝基苯（1，3-DNB），1，4-二硝基苯（1，4-DNB），2，4-二硝基苯甲醚（DNAN）、1，3，5-三硝基苯（TNB）、2，4，6-三硝基甲苯（TNT）、2-硝基苯甲醚（2-NAN）、4-硝基苯甲醚（4-NAN）和n-甲基-对硝基苯胺（MNA）。1-辛醇-水和空气-水分配系数的预测优化的TrapPE-UA力场与自适应偏置力分子动力学模拟，并与现有的实验数据进行比较。Log K-ow值的预测平均绝对偏差为0.2 log单位，而亨利定律常数的预测平均绝对偏差为0.5 log单位。另外两个模型，提出了五元环的含能材料，没有实验数据，在公开文献中：3，5-二硝基吡唑（DNP）和3-硝基-1，2，4-三唑-5-酮（NTO）。每个溶质周围的局部微观结构的调查表明，1-辛醇是能够形成氢键链周围的溶质，而很少有组织的微观结构观察周围的溶质在水中。
United-atom force fields, based on the Transferable Potentials for Phase Equilibria (TraPPE), are developed for twelve nitro-aromatic compounds, which include 2,4-dinitrotoluene (2,4-DNT), 2,6-dinitrotoluene (2,6-DNT), 3-nitrotoluene (3-NT), 4-nitrotoluene (4-NT), 1,3-dinitrobenzene (1,3-DNB), 1,4-dinitrobenzene (1,4-DNB), 2,4-dinitroanisole (DNAN), 1,3,5-trinitrobenzene (TNB), 2,4,6-trinitrotoluene (TNT), 2-nitroanisole (2-NAN), 4-nitroanisole (4-NAN) and n-methyl-p-nitroaniline (MNA). 1-Octanol-water and air-water partition coefficients are predicted for the optimized TraPPE-UA force field with adaptive biasing force molecular dynamics simulations, and compared to available experimental data. Log K-ow values are predicted with an average absolute deviation of 0.2 log units, while Henry's law constants are predicted to with an average absolute deviation of 0.5 log units. Two additional models are presented for energetic materials with five membered rings for which no experimental data are available in the open literature: 3,5-dinitropyrazole (DNP) and 3-nitro-1,2,4-triazole-5-one (NTO). Investigation of the local microstructure around each solute reveals that 1-octanol is able to form hydrogen bonded chains around the solute, while little organized microstructure was observed around the solutes in water.