Structure directing interactions in the crystals of o-hydroxyaryl/naphthyl derived aldimines: X-ray structure, Hirshfeld surface analysis, DFT and Molecular docking studies

Bhat M.A. Alabada R. Ajaj Y. Kaur M. Kaur H. Abduldayeva A. Sinha A. Saraswat V. Sood G. Almarhoon Z.M. Butcher R.J.
5 August 2024 Elsevier B.V.

Journal of Molecular Structure
2024 #1309

We have synthesized and thoroughly analyzed many intermolecular interactions present in (E)-1-(((3-nitrophenyl)amino)methylene)naphthalen-2(1H)-one (a), (E)-5-(diethylamino)-2-(((3-nitrophenyl)imino)methyl)phenol(b) and (E)-2-(((3-nitrophenyl)imino)methyl)phenol (c). Compounds a (keto-amine tautomeric form) and b, which have one molecule in the asymmetric unit, crystallize in the monoclinic crystal system with space groups P21/n and C2/c, respectively. Compound C, on the other hand, crystallizes in an orthorhombic crystal structure with the space group Pca21. The structural analysis showed that the construction of ring motifs to stabilize the crystal packing involves several interactions, including pi stacking interactions, N[sbnd]H…O, and C[sbnd]H…O interactions. Hirshfeld surface analysis has been used to examine their solid-state structures, including the evaluation of several energy frameworks. The results show that hydrogen bonds play a major role in the formation of the molecular sheets, and that electrostatic energy contribution dominates stability. Using fingerprint plots, it was possible to examine the variations and commonalities in the target compounds relative contributions from noncovalent interactions. In addition, B3LYP hybrid functional with 6- 311 G (d, p) level basis set was used in the density functional theory computations to optimize the structural coordinates. Through the examination of the molecular electrostatic potential surface, the chemically active areas of the target imine molecules were located. Additionally, using the internal ribosome entry site of the Hepatitis C virus ED42 (PDB-ID 3T4B), molecular docking of the title compounds was performed based on PASS analysis and literature findings.

DFT studies , Docking , Hirshfeld surface , PASS , Synthesis , X-ray diffraction

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Department of Chemistry, Islamic University of Science and Technology, Awantipora Kashmir, 192122, India
Al-Muthanna University, College of Pharmacy, Mathanna State, Samawah 6600, Iraq
Engineering Department, Faculty of Engineering and Computer science, German University of Technology, Halban, Oman
Department of Chemistry, Jain (Deemed-to-be) Univerity, Karnataka, Bengaluru, 560069, India
Department of Sciences, Vivekananda Global University Jaipur, Rajasthan, 303012, India
School of Basic and Applied Sciences, Shobhit University, Uttar Pradesh, Gangoh, 247341, India
Department of Health and Allied Sciences, Arka Jain University, Jharkhand, Jamshedpur, 831001, India
Department of Research Institute of Preventive Medicine named Acedemician E.Dalenov, Astana Medical University, Astana, 010000, Kazakhstan
School of Life and Applied sciences, Division of Research and Innovation, Uttaranchal University, Uttharakhand, Dehradun, India
Centre of Research Impact and Outcome, Chitkara University, Raipur, 140417, India
Chitkara Centre for Research and Development, Chitkara University, Himacahal Pradesh, 174102, India
Department of Chemistry, College of Science, King Saud University, Riyadh, 11451, Saudi Arabia
Department of Chemistry, Howard University, Washington DC, 20059, United States

Department of Chemistry
Al-Muthanna University
Engineering Department
Department of Chemistry
Department of Sciences
School of Basic and Applied Sciences
Department of Health and Allied Sciences
Department of Research Institute of Preventive Medicine named Acedemician E.Dalenov
School of Life and Applied sciences
Centre of Research Impact and Outcome
Chitkara Centre for Research and Development
Department of Chemistry
Department of Chemistry

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