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Stabilization of Supramolecular Assembly of N‐Substituted Benzylidene Acetohydrazide Analogs by Non‐Covalent Interactions: A Concise Experimental and Theoretical Approach
Author(s) -
Khalid Muhammad,
Ali Akbar,
Tariq Jahrukh,
Tahir Muhammad Nawaz,
Aliabad Hossein Asghar Rahnamaye,
Hussain Ishtiaq,
Ashfaq Muhammad,
Khan Muhammad Usman
Publication year - 2020
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.202002653
Subject(s) - natural bond orbital , intermolecular force , chemistry , hydrogen bond , van der waals force , atoms in molecules , supramolecular chemistry , molecule , homo/lumo , hyperconjugation , crystallography , non covalent interactions , crystal structure , computational chemistry , density functional theory , organic chemistry
Herein, the crystalline N ‐substituted benzylidene acetohydrazide derivatives: N ′‐(4‐bromo‐2‐fluorobenzylidene)‐2‐((6‐chloropyridin‐2‐yl)oxy) acetohydrazide ( BFBAH ) and 2‐((6‐chloropyridin‐2‐yl)oxy)‐ N ′‐(4‐methoxybenzylidene) acetohydrazide ( MOBAH ) were produced and the structures were characterized and confirmed by the NMR spectroscopy and single crystal analysis. SC‐XRD study disclosed that the molecules are connected with each other in the form of dimers through hydrogen bonding in the crystalline network of BFBAH and MOBAH . Additionally, the theoretical calculations were performed using the DFT/B3LYP/6‐311G(d,p) functional. The hyperconjugation and intermolecular hydrogen bonding were explored by using NBO analysis. Hirshfeld surface analysis analyzing intra and intermolecular interactions, uncovered that supramolecular assemblies have been stabilized by N−H⋅⋅⋅O and C−H⋅⋅⋅O intermolecular hydrogen bonds, as well as van der Waals interactions. The quantum theory of atoms in molecules (QT‐AIM) study corroborates that both significant N−H⋅⋅⋅O and C−H⋅⋅⋅O H‐bonds are strong in nature. Besides, global reactivity indices were computed via the energies of HOMO and LUMO orbitals.