Structural and energetic investigation on the host/guest inclusion process of benzyl isothiocyanate into β-cyclodextrin using dispersion-corrected DFT calculations

Abdelaziz Bouhadiba; Seyfeddine Rahali; Youghourta Belhocine; Hamza Allal; Leila Nouar; Mohamed Rahim

doi:10.1016/j.carres.2020.107980

Structural and energetic investigation on the host/guest inclusion process of benzyl isothiocyanate into β-cyclodextrin using dispersion-corrected DFT calculations

Carbohydr Res. 2020 May:491:107980. doi: 10.1016/j.carres.2020.107980. Epub 2020 Mar 18.

Authors

Abdelaziz Bouhadiba¹, Seyfeddine Rahali², Youghourta Belhocine³, Hamza Allal⁴, Leila Nouar⁵, Mohamed Rahim⁶

Affiliations

¹ Department of Petrochemical and Process Engineering, Faculty of Technology, 20 August 1955 University of Skikda, P.O. Box 26, El Hadaik Road, 21000, Skikda, Algeria; Laboratory of Computational Chemistry and Nanostructures, Department of Material Sciences, Faculty of Mathematical, Informatics and Material Sciences, University of 08 Mai 1945, Guelma, Algeria. Electronic address: a.bouhadiba@univ-skikda.dz.
² Department of Chemistry, College of Science & Arts at Al-Rass, Qassim University, P.O. 53, Saudi Arabia.
³ Department of Petrochemical and Process Engineering, Faculty of Technology, 20 August 1955 University of Skikda, P.O. Box 26, El Hadaik Road, 21000, Skikda, Algeria.
⁴ Department of Technology, Faculty of Technology, 20 August 1955 University of Skikda, P.O. Box 26, El Hadaik Road, 21000, Skikda, Algeria.
⁵ Laboratory of Computational Chemistry and Nanostructures, Department of Material Sciences, Faculty of Mathematical, Informatics and Material Sciences, University of 08 Mai 1945, Guelma, Algeria.
⁶ Department of Petrochemical and Process Engineering, Faculty of Technology, 20 August 1955 University of Skikda, P.O. Box 26, El Hadaik Road, 21000, Skikda, Algeria; Laboratory of Computational Chemistry and Nanostructures, Department of Material Sciences, Faculty of Mathematical, Informatics and Material Sciences, University of 08 Mai 1945, Guelma, Algeria.

PMID: 32199172
DOI: 10.1016/j.carres.2020.107980

Abstract

The formation of host-guest complex between benzyl isothiocyanate (BITC) and β-cyclodextrin (β-CD) was studied using dispersion-corrected density functional theory calculations. The complexation process was monitored using molecular docking simulations, natural bond orbital (NBO) technique, nuclear magnetic resonance (¹H NMR) chemical shift calculations and non-covalent interactions (NCI) analysis. All these approaches are consistent with experimental findings. The calculated complexation energy was negative indicating the formation of inclusion complex. The most stable complexation of BITC involves the inclusion of its aromatic moiety in β-CD cavity (model A) in accord with experimental NMR chemical shift data. The non-covalent interactions (NCI) based on the reduced density gradient (RDG) analysis reveal that mainly weak Van der Waals intermolecular interactions between BITC and β-CD provide and ensure stability for the complexation process.

Keywords: Benzyl isothiocyanate; DFT; Inclusion complex; NBO; NCI; β-Cyclodextrin.

MeSH terms

Density Functional Theory*
Isothiocyanates / chemistry*
Models, Molecular
Molecular Structure
beta-Cyclodextrins / chemistry*

Substances

Isothiocyanates
beta-Cyclodextrins
benzyl isothiocyanate
betadex