The C−NO2 bond dissociation energies of some nitroaromatic compounds: DFT study |
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Authors: | Juxiang Shao Xinlu Cheng Xiangdong Yang |
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Affiliation: | (1) Department of Physics and Electronic Information, Yibin University, YiBin, 644007, People’s Republic of China;(2) Institute of Atomic and Molecular Physics, Sichuan University, Chengdu, 610065, People’s Republic of China |
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Abstract: | The C−NO2 bond dissociation energies in nitrobenzene; 3-amino-nitrobenze; 4-amino-nitrobenze; 1,3-dinitrobenzene; 1,4-dinitrobenzene; 2-methyl-nitrobenzene; 4-methyl-nitrobenzene; and 1,3,5-trinitrobenzene nitroaromatic molecules, are computed using B3LYP, B3PW91, B3P86 three-parameter hybrid Density Functional Theory (DFT) methods in conjunction with 6-31G** basis set. By comparing the computed energies and experimental ones, it is found that B3P86/6-31G** is not capable of predicting the satisfactory bond dissociation energy (BDE). The BDEs computed with both B3LYP/6-31G** and B3PW91/6-31G** for the nitroaromatic molecules are closer to the experimental ones than those obtained with B3P86/6-31G**. But, when compared with the experimental one, the BDE from the B3LYP/6-31G** has the maximum deviation, which is completely outside our desired target accuracy for chemical predictions (less than 2.00 kcal mol−1). Therefore, we suggest B3PW91/6-31G** method as a reliable method of computing the BDE for removal of the nitrogen dioxide group in the nitroaromatic compounds. In addition, the C−NO2 BDEs for 2,4,6-trinitrotoluene (TNT), triaminotrinitrobenzene (TATB), diaminotrinitrobenzene (DATB), and picramide are studied with B3PW91/6-31G** method. |
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Keywords: | Density functional theory Bond dissociation energies Nitroaromatic compounds |
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