Startseite Naturwissenschaften Exploring the dynamics of halogen and hydrogen bonds in halogenated coumarins
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Exploring the dynamics of halogen and hydrogen bonds in halogenated coumarins

  • Mebin Varghese , Jisha Mary Thomas , Abdullah Y. Alzahrani und Renjith Thomas EMAIL logo
Veröffentlicht/Copyright: 15. Februar 2024
Zeitschrift für Physikalische Chemie
Aus der Zeitschrift Zeitschrift für Physikalische Chemie Band 238 Heft 9

Abstract

Halogen bonds find application in supramolecular chemistry, DNA Holliday junction, drug design, organic catalysis and various other fields. Coumarin derivatives are high in demand due to their application in photochemotherapy, drugs and other cancer treatments. Halogenated coumarins are widely known for their biological activities. There exists a competition between the halogen bond and hydrogen bond in singly hydrated halogenated coumarins. The competition between hydrogen and halogen bonding interactions in 3-halogenated 4-hydroxyl coumarin [coumarin derivative; halogen, X = F (A), Cl (B), Br (C), I (D)] with water molecule in the corresponding binding regions C3–X and C2=O4 is studied. This study was conducted using PBE0 D3BJ with augmented correlation consistent basis set in order to include the diffuse functions. Improved findings for non-bonded distances and much more distinct intramolecular effects were obtained using BJ-damping. In the singly-hydrated systems, the water molecule forms a hydrogen bond with C2=O4 in all the halogenated molecules, whereas halogen bonding between the water oxygen and C2–X exists only in the case of X = Br (C) and I (D). The absence of a halogen-bonded structure in singly-hydrated chlorine and fluorine substituted coumarin derivative is therefore attributed to the competing hydrogen-bonding interaction with C2=O4. RDG scatter plot as well QTAIM analysis implied that halogen bond exists between water molecule and the coumarin derivative. Further, the most modern local energy decomposition (LED) analysis of intermolecular interaction was also studied using DLPNO-CCSD(T). Finally, ab initio molecular dynamics was also performed.

Keywords: hydrogen bond; halogen bond; non-covalent interactions; DFT; AIMD; coumarins
Corresponding author: Renjith Thomas, Department of Chemistry, St Berchmans College (Autonomous), Mahatma Gandhi University, Changanassery, Kerala 686101, India; and Centre for Theoretical and Computational Chemistry, Department of Chemistry, St Berchmans College (Autonomous), Mahatma Gandhi University, Changanassery, Kerala 686101, India, E-mail:

Acknowledgments

SEAGrid (http:www.seagrid.org) is acknowledged for computational resources and services for the selected results used in this publication.

  1. Ethical approval: Not applicable.

  2. Author contributions: All authors have accepted responsibility for the entire content of this manuscript and approved its submission. M. V.: Simulation, formal analysis, Revised manuscript writing J. M. T.: Analysis, writing draft, formal analysis, A. Y. A.: Analysis, writing revised draft, formal analysis, R. T.: Conceptualization, methodology, resources, supervision, writing.

  3. Competing interests: Authors state no conflict of interest.

  4. Research funding: None declared.

  5. Data availability: None declared.

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Supplementary Material

This article contains supplementary material (https://doi.org/10.1515/zpch-2023-0570).

Received: 2023-12-26
Accepted: 2024-01-21
Published Online: 2024-02-15
Published in Print: 2024-09-25

© 2024 Walter de Gruyter GmbH, Berlin/Boston

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  4. Original Papers
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https://doi.org/10.1515/zpch-2023-0570
Schlagwörter für diesen Artikel
hydrogen bond; halogen bond; non-covalent interactions; DFT; AIMD; coumarins

Artikel in diesem Heft

  1. Frontmatter
  2. Review Article
  3. The assessment of pollutant waste generated by battery and its effect on the environment: a concise review
  4. Original Papers
  5. Biosynthesis of ZnO/Ag nanocomposites heterostructure for efficient photocatalytic degradation of antibiotics and synthetic dyes
  6. Kinetics, equilibrium and thermodynamics investigations of polypyrrole and polyaniline composites with Oryza sativa biomass for the removal of Nitenpyram insecticide
  7. Remediation of pesticides, acetamiprid and imidacloprid from aqueous solutions using cellulose derived from sawdust of Populus nigra
  8. Rice husk composite with polyaniline, sodium alginate and polypyrrole: naphthalene adsorption kinetics, equilibrium and thermodynamic studies
  9. Graphene oxide composite as a novel corrosion inhibitor for N80 steel in 15 % HCl: experimental and quantum chemical examinations
  10. Molecular level interaction, molecular structure, chemical reactivity, electronic and topological exploration and docking studies of 1-acetyl-4-piperidinecarboxylic acid
  11. Exploring the dynamics of halogen and hydrogen bonds in halogenated coumarins
  12. Electrochemical sensing and detection of phosgene and thiophosgene chemical warfare agents (CWAs) by all-boron B38 fullerene analogue: a DFT insight
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