Stereochemical, single crystal X-ray structural, Hirshfeld surface and cyclic voltammetric studies of N-cyclohexylcarbamoyl-3-isopropyl-2,6-bis(phenyl)piperidin-4-one and N-cyclohexylcarbamoyl-3,3-dimethyl-2,6-bis(4-fluorophenyl)-piperidin-4-one

Abstract

• Twist boat conformation of N -cyclohexylcarbamoylpiperidin-4-one was proved by NMR and XRD. • Single crystal X-ray structural and Hirshfeld surface analysis of 1 and 2 were performed. • Computational and cyclic voltammetric studies were also performed. N- Cyclohexylcarbamoyl-3-isopropyl-2,6-bis(phenyl)piperidin-4-one (1) and N- Cyclohexylcarbamoyl-3,3-dimethyl-2,6-bis(4-fluorophenyl)piperidin-4-one (2) were synthesized and characterized by IR, 1 H NMR, 13 C NMR, HOMOCOSY, NOESY, HSQC and HMBC. Single crystal X-ray diffraction study was performed for 1 and 2 . Both the compounds (1 and 2) crystallized in triclinic crystal system with P -1 space group. From the XRD analysis results it is observed that the conformation of the heterocyclic ring in 1 and 2 is twist boat. The computational study was performed and the structures were optimized using DFT – B3LYP with the 6 - 31G basis set. Hirshfeld surface analysis was also carried out and the contributing intermolecular interactions which stabilizes the crystal structures are quantified. It exemplifies the predominant contribution of van der Waals interaction in the packing of both the crystal structures. Cyclic voltammetric studies were also performed and discussed. From the CV analysis it is observed that 2 exhibit the high specific capacitance value even at higher scan rate.