Citation: TANG Hai-Fei, TIAN Qing-Ping, LI Guo-Yuan, JIAN Xin-Tian, REN Li, ZHOU Ge-Rong. Theoretical Investigations into the Intermolecular Hydrogen-bonding Interactions between Azacyclopentane-2-one and N-Methylol Ethanone[J]. Chinese Journal of Structural Chemistry, ;2014, 33(1): 135-147. shu

Theoretical Investigations into the Intermolecular Hydrogen-bonding Interactions between Azacyclopentane-2-one and N-Methylol Ethanone

1.
a Department of Pharmacy, Shanxi Medical University, Taiyuan 030001, China;
2.
b Bureau of Science and Technology, Public Security Department of Shanxi Province, Taiyuan 030001, China

Corresponding author: TIAN Qing-Ping,
Received Date: 18 July 2013
Available Online: 11 December 2013

The structures of the complexes formed between N-methylol ethanone (model molecule of ceramide) and azacyclopentane-2-one (the model molecule of azone) have been fully optimized at the B3LYP/6-311++G^** level. The intermolecular hydrogen bonding interaction energies have been calculated by using the B3LYP/6-311++G^**, B3LYP/6-311++G(2df,2p), MP2(full)/6-311++G^** and MP2(full)/6-311++G(2df,2p) methods, respectively. The results show that strong O-H…O=C, N-H…O=C and C-H…O=C hydrogen bonds could exist between azacyclopentane-2-one and N-methylol ethanone. The formation of the complexes might change the conformation of ceramide molecule and thus cause better percutaneous permeation for the drugs. This is perhaps the origin of the permeation enhances the activity of azone for medicament, as is in accordance with the experimental results. The hydrogen-bonding interactions follow the order of (a) >(c) >(b) >(d) >(g)≈(e)≈(i) >(h) >(f). The analyses of frequency, NBO, AIM and electron density shift are used to further reveal the nature of the complex formation. In the range of 263.0~328.0 K, the complex is formed via an exothermic reaction, and the solvent with lower temperature and dielectric constant is favorable to this process.
- N-methylol ethanone,
- azacyclopentane-2-one,
- intermolecular hydrogen bond,
- temperature effect,
- MP2 (full)
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