Internal Rotation of 2-, 3- and 4-Pyridine Carboxaldehydes and Their Chalcogen Analogues (S and Se) in the Gas and Solution Phases: A Theoretical Investigation

Abdallah, Hassan H.; Yeoh, P. H.; Rhyman, Lydia; Alswaidan, Ibrahim A.; Fun, Hoong Kun; Umar, Yunusa; Ramasami, Ponnadurai

doi:10.1007/s10953-016-0499-1

J Solution Chem

2016

DOI: 10.1007/s10953-016-0499-1

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Internal Rotation of 2-, 3- and 4-Pyridine Carboxaldehydes and Their Chalcogen Analogues (S and Se) in the Gas and Solution Phases: A Theoretical Investigation

Hassan H. Abdallah

P. H. Yeoh

Lydia Rhyman

et al.

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Cited by 11 publications

References 24 publications

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Theoretical Study on Geometry and Intramolecular Hydrogen Bonding in 8‐Hydroxy‐1‐Naphthaldehyde

El-Rayyes

Umar

2021

Bulletin Korean Chem Soc

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Calculated geometrical parameters in the gas phase and solvents for 8-hydroxy-1-naphthaldehyde (8H1N) were carried out using density functional theory (DFT) at the 6-311++G(d,p) level, and the Time Dependent-DFT/6-311++G(d,p) method was used for the excited state calculations. 8H1N is found to exist in two main conforms, the cis-cis conformer (where the dihedral angels C 3 C 2 -OH is 0 , C 3 C 8 -CO is 0 ) was found to be more stable than the trans-trans form (where the dihedral angels C 3 C 2 -OH is 180 , C 3 C 8 -CO is 180.0 ) by about 6.47 kcal/mol. The possibility of intramolecular hydrogen bonding between the hydroxyl (OH) and aldehyde (CHO) moieties is predicted. The hydrogen bond becomes stronger in polar solvents and in the excited state. Energies of 8H1N-one water molecule complexes are calculated using the DFT-D3 level of theory and results indicate that at least one solvent molecule is required to assist the proton transfer process.

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Theoretical Study on Geometry and Intramolecular Hydrogen Bonding in 8‐Hydroxy‐1‐Naphthaldehyde

El-Rayyes

Umar

2021

Bulletin Korean Chem Soc

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Theoretical investigation of the molecular structure, vibrational spectra, and molecular docking of tramadol using density functional theory

Umar

Abdalla

Haque

et al. 2019

J Chinese Chemical Soc

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The optimized molecular structures, harmonic vibrational wavenumbers, and the corresponding vibrational assignments of (1S,2S)-tramadol and (1R,2R)-tramadol are computationally examined using the B3LYP density functional theory method together with the standard 6-311++G(d,p) and def2-TVZP basis sets. The optimized structures show that phenolic rings of both 1R,2R and 1S,2S tramadol adopt planar geometry, which are slightly distorted due to the substitution at the metaposition; and the six-membered cyclohexane adopts a slightly distorted chair conformation. The 1S,2S enantiomer is energetically more favorable than 1R,2R with the energy differences of 1.32 and 1.03 kcal/mol obtained at B3LYP/6-311++G (d,p) and B3LYP/Def2-TVZP levels, respectively. The analysis of the binding pocket in the silico molecular docking with the m-opioid receptor shows that it originated two clusters with the 1S,2S enantiomer and one cluster with the 1R,2R enantiomer of tramadol. The results point to a more stable complex of the m-opioid receptor with the 1R,2R enantiomer of tramadol. K E Y W O R D SDFT, frontier molecular orbital, molecular docking, tramadol, vibrational spectra

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The Application of Box-Behnken-Design in the Optimization of Kinetic Spectrophotometry and Computational Studies to Determine and Assessing Eco-Scale to Green Analytical Chemistry for Labetalol

Haque,

Aldhafeeri,

Rahman

et al. 2024

J Pharm Innov

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Internal Rotation of 2-, 3- and 4-Pyridine Carboxaldehydes and Their Chalcogen Analogues (S and Se) in the Gas and Solution Phases: A Theoretical Investigation

Cited by 11 publications

References 24 publications

Theoretical Study on Geometry and Intramolecular Hydrogen Bonding in 8‐Hydroxy‐1‐Naphthaldehyde

Theoretical Study on Geometry and Intramolecular Hydrogen Bonding in 8‐Hydroxy‐1‐Naphthaldehyde

Theoretical investigation of the molecular structure, vibrational spectra, and molecular docking of tramadol using density functional theory

The Application of Box-Behnken-Design in the Optimization of Kinetic Spectrophotometry and Computational Studies to Determine and Assessing Eco-Scale to Green Analytical Chemistry for Labetalol

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