Structural analysis and theoretical studies of 2-(2-chlorobenzylidene) malononitrile (CS) “a riot controlling agent”
Shaikh M.Z. Abduldayeva A. Shatat A.S. Kaur M. Kaur H. Al Khatib A.O. Dev A. Gupta M. Siva Prasad G.V. Sinha A. Almutairi T.M. Butcher R.J. Bhat M.A.
15 November 2024Elsevier B.V.
Journal of Molecular Liquids
2024#414
In solvent methanol, malononitrile and 2-chlorobenzaldehyde were stirred in the presence of base piperidine to synthesise the target chemical 2-(2-chlorobenzylidene) malononitrile (CS). The crystal structure of the target compound C10H5ClN2 has been elucidated through X-ray crystallographic analysis. It crystallises in the monoclinic crystal system within the P21 space group, containing four molecules per asymmetric unit. The unit cell dimensions are a = 3.8825(3) Å, b = 21.0202(18) Å, c = 21.3481(18) Å, and β = 95.096(4)°. The phenyl and malononitrile groups, which make up the molecular components, are each planar but slanted towards one another at a dihedral angle of 12.7° (4). Besides this, target molecule is also stabilized by hydrogen bonding, halogen bonding and π stacking interactions. Solid-state structure has been analysed through Hirshfeld surface analysis, including the evaluation of the different energy frameworks, indicating that the molecular sheets are primarily formed by hydrogen bonds and halogen bonds and the stabilization is dominated via the electrostatic energy contribution. Fingerprint plots were carried out to study the relative contribution of noncovalent interactions in the target compound CS. Further, the density functional theory calculations were employed using B3LYP hybrid functional with 6-311++G level basic set to optimize the structural coordinates in gas phase and in different solvents (chloroform, water, and methanol). The chemically active regions of the target compound were identified by the analysis of molecular electrostatic potential surface. Further, from PASS analysis and literature reports, molecular docking of title compounds was carried out with human transient receptor potential ankyrin 1 ion channel (hTRPA1) (PDB-ID 6PQO). ΔGb (docking energy) and inhibition constant was calculated to be −7.53 kcal/mol and 3.33 μM respectively, with the target ion channel.
DFT studies , Docking , Hirshfeld surface , PASS , X-ray diffraction
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Shree Bahubhai Mafatlal Polytechnic College, Irla, Vile Parle(W), Mumbai, 400056, India
Department of Research Institute of Preventive Medicine Named Acedemician E. Dalenov, Astana Medical University, Astana, 010000, Kazakhstan
Management Information Systems Department, College of Administrative Sciences, Applied Science University, Al Eker, Bahrain
Department of Chemistry, Jain (Deemed-to-be) University, Karnataka, Bengaluru, 560069, India
Department of Sciences, Vivekananda Global University, Rajasthan, Jaipur, 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
Hourani Center for Applied Scientific Research, Al-Ahliyya Amman University, Jordan
Centre of Research Impact and Outcome, Chitkara University, Punjab, Rajpur, 140417, India
Chitkara Centre for Research and Development, Chitkara University, Himachal Pradesh, 174103, India
Department of Chemistry, Raghu Engineering College Visakhapatnam, Andhra Pradesh, 531162, India
School of Applied and Life Sciences, Division of Research and Innovation, Uttaranchal University, Uttarakhand, Dehradun, 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, Islamic University of Science and Technology, Awantipora, Pulwama, 192122, India
Shree Bahubhai Mafatlal Polytechnic College
Department of Research Institute of Preventive Medicine Named Acedemician E. Dalenov
Management Information Systems Department
Department of Chemistry
Department of Sciences
School of Basic and Applied Sciences
Department of Health and Allied Sciences
Hourani Center for Applied Scientific Research
Centre of Research Impact and Outcome
Chitkara Centre for Research and Development
Department of Chemistry
School of Applied and Life Sciences
Department of Chemistry
Department of Chemistry
Department of Chemistry
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