Theoretical Investigation of the Complexation Reaction of Procaine-hydrochloride by β-cyclodextrin

IF 1.4 Q3 CHEMISTRY, MULTIDISCIPLINARY

Physical Chemistry Research Pub Date : 2020-03-01 DOI:10.22036/PCR.2020.205547.1691

M. Azayez, T. Fergoug, N. Meddah-Araibi, C. Zelmat, Y. Bouhadda

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引用次数: 3

Abstract

Abstract. . Quantum-chemical calculations were performed to study the complexation of drug molecule procaine hydrochloride with beta cyclodextrin (β-CD) in the gas phase and in water. The inclusion process was optimized by the semi empirical method PM3 and the obtained complex structure was further refined by ONIOM method (DFT: PM3). It is found that (B3LYP/6-31G(d,p) : PM3) provides the best energy minimum for the complex, compared to M06-2X and WB97XD functional. Given the energy profile, the configuration of the complex formed indicates that the benzene ring is completely included in the hydrophobic cavity of the β-CD. The thermodynamic parameters analysis has shown that the procaine/β-CD complexation is enthalpically favorable, and the complex is well structured. Natural bond orbital (NBO) analysis indicates that no hydrogen bond interaction exists, and the procaine/β-CD complex is mainly stabilized by Van der Waals forces. 1D 1H NMR spectra analysis shows that the procaine molecule penetrates into the cavity of this CD with the aromatic ring.

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β-环糊精与盐酸普鲁卡因络合反应的理论研究

摘要采用量子化学方法研究了药物分子盐酸普鲁卡因与β-环糊精(β-CD)在气相和水中的络合作用。采用半经验方法PM3对包合工艺进行了优化，并用niom方法(DFT: PM3)对得到的复合结构进行了进一步细化。与M06-2X和WB97XD相比，(B3LYP/6-31G(d,p): PM3)为配合物提供了最佳的能量最小值。根据能量谱，所形成的络合物的构型表明苯环完全包含在β-CD的疏水腔中。热力学参数分析表明，普鲁卡因/β-CD配合物具有良好的热稳定性，配合物结构良好。自然键轨道(NBO)分析表明，产物不存在氢键相互作用，普鲁卡因/β-CD配合物主要靠范德华力稳定。1D 1H核磁共振谱分析表明，普鲁卡因分子通过芳香环进入CD的腔内。

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来源期刊

Physical Chemistry Research CHEMISTRY, MULTIDISCIPLINARY-

CiteScore

2.70

自引率

8.30%

发文量

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