Citation: Li Qianggen, Mao Shuang, Liu Liuxie, Cai Wanfei, Zheng Yan. Theoretical Study of the Alcoholysis Reaction Mechanism of Temazepam[J]. Chemistry, ;2016, 79(10): 968-974. shu

Theoretical Study of the Alcoholysis Reaction Mechanism of Temazepam

1.
College of Chemistry and Material Science, Sichuan Normal University, Chengdu 610068

Corresponding author: Li Qianggen,
Received Date: 16 February 2016
Available Online: 20 April 2016
Fund Project:

Abuse of the large number sedative hypnotics has brought serious negative impacts to food safety, and also threatens people's health and life safety. In the present work, using temazepam (TMZ) as an example, we explore theoretically the alcoholysis of benzodiazepines in neutral and acidic methanol solvent by employing the B3LYP/6-311+G^** and MP2/6-311+G^** methods. The results indicated that the degradation reactions of TMZ by N1-C2 bond broken in neutral and acidic methanol solution (Path 2 and Path 3) are difficult to process based on the analysis of kinetics and thermodynamics, while the degradation reaction of TMZ by C3-N4 bond broken (Path 1) is feasible in neutral methanol solution according to the dynamic analysis. The reaction involves one (85.7kJ/mol (ΔG^≠)) or two explicit solvent molecules (81.6 kJ/mol (ΔG^≠)), which act(s) as proton acceptor and donor to accelerate the reaction. Thus, Path 1 should be the dominated alcoholysis reaction path of TMZ in methanol solution, and the results are consistent with the experimental results.
- Temazepam,
- Benzodiazepines,
- Alcoholysis,
- B3LYP,
- Solvent effect
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沈阳化工大学材料科学与工程学院沈阳 110142