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

期刊介绍： The motivation for this new journal is the tremendous increasing of useful articles in the field of Physical Chemistry and the related subjects in recent years, and the need of communication between Physical Chemists, Physicists and Biophysicists. We attempt to establish this fruitful communication and quick publication. High quality original papers in English dealing with experimental, theoretical and applied research related to physics and chemistry are welcomed. This journal accepts your report for publication as a regular article, review, and Letter. Review articles discussing specific areas of physical chemistry of current chemical or physical importance are also published. Subjects of Interest: Thermodynamics, Statistical Mechanics, Statistical Thermodynamics, Molecular Spectroscopy, Quantum Chemistry, Computational Chemistry, Physical Chemistry of Life Sciences, Surface Chemistry, Catalysis, Physical Chemistry of Electrochemistry, Kinetics, Nanochemistry and Nanophysics, Liquid Crystals, Ionic Liquid, Photochemistry, Experimental article of Physical chemistry. Mathematical Chemistry.

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