Molecular modeling study of structures, Hirschfield surface, NBO, AIM, RDG, IGM and 1HNMR of thymoquinone/hydroxypropyl-β-cyclodextrin inclusion complex from QM calculations

被引：30

作者：

Rayene, Kadri ^{[1
]}

Imane, Djellala ^{[2
]}

Abdelaziz, Bouhadiba ^{[3
]}

Leila, Nouar ^{[2
]}

Fatiha, Madi ^{[2
]}

Abdelkrim, Guendouzi ^{[4
,5
]}

Bouzid, Gassoumi ^{[6
]}

Ismahan, Lafifi ^{[2
]}

Brahim, Houari ^{[4
]}

Rabah, Oumeddour ^{[7
]}

机构：

[1] Univ 8 Mai 1945, Dept Mat Sci, Lab Appl Chem, Fac Math Informat & Mat Sci, Guelma, Algeria

[2] Univ 8 Mai 1945, Dept Mat Sci, Lab Comp Chem & Nanostruct, Fac Math Informat & Mat Sci, Guelma, Algeria

[3] Univ 20 Aout 1955, Skikda, Algeria

[4] Univ Saida, Dept Chem, Fac Sci, Lab Chem Synth Properties & Applicat, Saida, Algeria

[5] Univ Abu Bekr Belkaid Tlemcen, Lab Appl Thermodynam & Modeling Mol, Tilimsen, Algeria

[6] Univ Monastir, Lab Adv Mat & Interfaces LIMA, Fac Sci Monastir, Ave Environm, Monastir 5000, Tunisia

[7] Univ 8 Mai 1945, Lab Ind Anal & Mat Engn, Dept Mat Sci, Fac Math Informat & Mat Sci, Guelma, Algeria

来源：

JOURNAL OF MOLECULAR STRUCTURE | 2022年 / 1249卷

关键词：

inclusion complex; QTAIM; IGM; Dispersion correction; Hirshfeld surface; RDG; DENSITY-FUNCTIONAL THEORY; INTERMOLECULAR INTERACTIONS; THYMOQUINONE; DFT; SOLUBILITY; STABILITY; LIPOSOMES; BINDING; CANCER; STATE;

D O I：

10.1016/j.molstruc.2021.131565

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

In this work, the thymoquinone (TQ)/hydroxypropyl-beta-cyclodextrin (HP beta-CD) inclusion complex has been investigated employing quantum mechanical calculations in gas phase and in water. Complexation energies, geometries parameters and thermodynamic parameters Delta H degrees, Delta S degrees and Delta G degrees have been investigated and analyzed. The results obtained clearly indicate that the complexation process with Orientation B (TQ enters into the cavity of HP beta-CD from its wide side by C2H6 group) is energetically favored than that of Orientation A (TQ penetrates the HP beta-CD cavity from its wide side by methyl group). Time-dependent (TD)-DFT analysis performed in water using polarizable continuum model (PCM) calculations reveal that the main absorption bands of thymoquinone arise from the pi ->pi* transition, after encapsulated by hydroxypropyl-beta-cyclodextrin to form inclusion complexes. (HOMO-LUMO) energy and global reactivity descriptor values were evaluated. The results of electrophilicity based charge transfer (ECT) indicate that, the charge transfer occurs from the host to the guest. The Hirschfield surface is also investigated. From QTAIM analysis, del(2) rho(r) > 0 and H(r) > 0 at critical points for all intermolecular interactions correspond to weak H-bonds and affirm dominance of electrostatic interactions. Also, the ratio -G(r)/V(r) > 1 confirms the presence of weak hydrogen bonding and van der Waals interactions stabilizing the complex. In addition, the reduced density gradient (RDG) and the independent gradient model (IGM) methods were used to reveal and distinguish between attractive interactions such hydrogen bonds, repulsive interactions and van der Waals interactions. At last, H-1 NMR chemical shifts were computed with gage-including atomic orbital (GIAO) and compared with experimental results. (C) 2021 Elsevier B.V. All rights reserved.

引用

页数：13