Non-covalent interactions abetted supramolecular arrangements of N-Substituted benzylidene acetohydrazide to direct its solid-state network

Author(s)

Khalid, Muhammad ^[1] ; Ali, Akbar ^{[2, 3]} ; Khan, Muhammad Usman ^{[4, 5]} ; Tahir, Muhammad Nawaz ^[6] ; Ahmad, Anees ^[7] ; Ashfaq, Muhammad ^[6] ; Hussain, Riaz ^[5] ; de Alcantara Morais, Sara Figueiredo ^[8] ; Carmo Braga, Ataualpa Albert ^[8]

Affiliation

^[1] Khwaja Fareed Univ Engn & Informat Technol, Dept Chem, Rahim Yar Khan 64200 - Pakistan

^[2] Univ Sargodha, Dept Chem, Sargodha 40100 - Pakistan

^[3] Univ Malakand, Dept Chem, Lower Dir 18800, Khyber Pakhtunk - Pakistan

^[4] Govt Coll Univ, Dept Appl Chem, Faisalabad 38000 - Pakistan

^[5] Univ Okara, Dept Chem, Okara 56300 - Pakistan

^[6] Univ Sargodha, Dept Phys, Sargodha - Pakistan

^[7] Univ Sao Paulo, Inst Quim Sao Carlos, BR-13560970 Sao Carlos, SP - Brazil

^[8] Univ Sao Paulo, Dept Quim Fundamental, Inst Quim, Ave Prof LineuPrestes 748, BR-05508000 Sao Paulo - Brazil

• Document type: Journal article
• Source: Journal of Molecular Structure; v. 1230, APR 15 2021.
• Web of Science Citations: 0

Abstract

Intra-molecular hydrogen bond modulation of compounds positively impacts their solubility, permeability and as well as potency in the field of medicinal chemistry. Herein, N-substituted benzylidene acetohydrazide derivative: (Z)-2-((6-chloropyridin-2-yl)oxy)-N'-(2-hydroxy-3-methoxybenzylidene)ace tohydrazide (HOBAH), a novel solid state network was synthesized efficiently via sono-chemical approach. The structural characterization of HOBAH was achieved by single crystal analysis which exposed intra-molecular N-H center dot center dot center dot O, O-H. N bonding and intermolecular N-H center dot center dot center dot O, O-H center dot center dot center dot O and comparatively weak C-H center dot center dot center dot O hydrogen bonding being responsible for the crystal packing. Theoretical calculations by applying the density functional theory (DFT) at DFT/B3LYP/6-311G(d,p) were completed. The characteristic of HOBAH was evaluated from a relaxed PES scan analysis and the HOBAH conformations with minimum energy have been identified. Hirshfeld surface (HS) and the quantum theory of atoms in molecules (QT-AIM) analyses bolstered in quantifying the existing non-covalent interactions. QT-AIM analysis unveiled that strong N-H center dot center dot center dot O-H and C=O center dot center dot center dot H-O hydrogen bonds (HBs) and other van der Waals interactions were responsible for the stabilization of these solid state networks. All non-covalent interactions with positive laplacian of electron density (del rho(2)) values from QT-AIM analysis corroborated well with the internal charge transfer and the hyper-conjugative interactions explored by NBO analysis. Moreover, all significant results were endorsed by both NPA and FMO evaluations. FMO analysis later assisted in the calculation of global reactivity indices. However, local reactivity indices were computed with Fukui function calculations. Lastly, molecular electrostatic potential (MEP) was plotted which confirmed the nucleophilic and electrophilic sites of HOBAH as elaborated by the reactivity indices. (C) 2020 Elsevier B.V. All rights reserved. (AU)

• FAPESP's process: 15/20084-0 - Total Synthesis of (-)-Brussonol, (+)-Komaroviquinona and its analogs targeting potential candidates with trypanocidal activity
• Grantee: Anees Ahmad
• Support Opportunities: Scholarships in Brazil - Post-Doctoral