Inclusion Complex Formation of β-Cyclodextrin with the Nonsteroidal Anti-inflammatory Drug Flufenamic Acid: Computational Study

Youghourta Belhocine,^a,b@ Abdelaziz Bouhadiba,^a,c Mohamed Rahim,^a,c Leila Nouar,^c Imene Djilani,^c and Djamel Eddine Khatmi^c

^aFaculty of technology, Department of Petrochemical and Process Engineering, University of 20 Août 1955 Skikda, Algeria

^bLaboratory of Materials Chemistry, Campus Shaab Ersas, Faculty of Exact Sciences, University Constantine 1, Algeria

^cLaboratory of Computational Chemistry and Nanostructures, Department of Material Sciences, Faculty of Mathematical, Informatics and Material Sciences, University of 08 Mai 1945 Guelma, Algeria

^@Corresponding author E-mail: jugurtha1977@gmail.com

DOI: 10.6060/mhc170829b

Macroheterocycles2018 11(2) 203-209

Structural study and thermodynamics of complexation between β-cyclodextrin (β-CD) and flufenamic acid (FFA) are explored by means of several quantum chemical methods. The different orientation modes of FFA in the cavity of β-CD are studied. PM3MM, ONIOM2 and DFT methods show that the complex FFA/β-CD in A orientation is found to be the most favorable energetically. The statistical thermodynamic calculations at 1 atm and 298.15 K reveal that the complexation process is exothermic and enthalpically driven. Finally, the calculated chemical shifts of free FFA and its complex at B3LYP/6-31G(d) level by employing the Gauge-Including Atomic Orbital (GIAO) method are in good agreement with NMR experimental data.

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Inclusion Complex Formation of β-Cyclodextrin with the Nonsteroidal Anti-inflammatory Drug Flufenamic Acid: Computational Study

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