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Evidences of noncovalent interactions between indole and dichloromethane under different solvent conditions

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Abstract

Context

Theoretical investigation of indole (IND) and its binary combination with dichloromethane (DC) in various solvents were computed to track the impact of molecular interactions on spectral characteristics. When transitioning from plain drug to complexes, different modes of IND display a substantial shift in peak location. The 3561.26 cm−1 band shows (~15.58 cm−1) red shift upon dilution. The geometry in various solvents was calculated using quantum chemical calculation utilizing density functional theory (DFT). The highest ALIE values are located at the indole skeleton and on complexation with DC, and the ring atoms become more electron rich. The atom-centered density matrix propagation (ADMP) molecular dynamic (MD) calculation shows that the geometries optimized through the DFT calculation match the global minima effectively. MD simulations indicate that indole is more stable in water and methanol.

Methods

DFT studies have been employed to study the interaction between indole and dichloromethane. CAM-B3LYP/6-311++G(d)(6D,7F) level of theory was employed using Gaussian 16 W suite. Quantum topological descriptors were discussed using quantum theory of atoms in molecules (QTAIM) with the help of Multiwfn software. Reduced density gradient (RDG) plot describes the nature of the interaction, while average local ionization energy (ALIE) explained the variation in local ionization energy of the molecular surface before and after complexation.

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Funding

The authors express their gratitude to Princess Nourah Bint Abdulrahman University Researchers Supporting Project (number PNURSP2023R1), Princess Nourah Bint Abdulrahman University, Riyadh, Saudi Arabia.

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Authors and Affiliations

  1. Department of Chemistry, College of Science, Princess Nourah Bint Abdulrahman University, P.O. Box 84428, Riyadh, 11671, Saudi Arabia

    Jamelah S. Al-Otaibi

  2. Thushara, Neethinagar-64, Kollam, Kerala, India

    Y. Sheena Mary & Y. Shyma Mary

  3. Department of Chemistry, St. Berchmans College (Autonomous), Mahatma Gandhi University, Changanassery, Kerala, India

    Renjith Thomas

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Contributions

Jamelah S. Al-Otaibi: software, supervision, manuscript preparation, and data analysis. Y. Sheena Mary: supervision, manuscript preparation, conceiving the problem, and data analysis. Y. Shyma Mary: manuscript preparation, conceiving the problem, and data analysis and correction. Renjith Thomas: manuscript preparation, conceiving the problem, and data analysis and correction.

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Correspondence to Jamelah S. Al-Otaibi.

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Al-Otaibi, J.S., Mary, Y.S., Mary, Y.S. et al. Evidences of noncovalent interactions between indole and dichloromethane under different solvent conditions. J Mol Model 29, 246 (2023). https://doi.org/10.1007/s00894-023-05623-3

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