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Computational Investigations on Stability and Equilibrium Composition of (Z)-indol-3-ylidenemethanol: An Enol-tautomer of 1H-indole-3-carbaldehyde via DFT Approach

[ Vol. 8 , Issue. 3 ]

Author(s):

Ibrahim Asiata Omotayo, Oyebamiji Abel Kolawole and Semire Banjo*   Pages 194 - 210 ( 17 )

Abstract:


Background: The stability and molecular properties of 1H-indole-3- carbaldehyde (A) and its tautomer, (Z)-indol-3-ylidenemethanol (B) are examined using B3LYP/6-311++G(d,p), M06/6-311++G(d,p), wB97xD/6-311++G(d,p) and MP2/6- 311++G(d,p) methods.

Method: The molecular reactivity indices calculated and discussed are the EHOMO, ELUMO, Δ(EHOMO-LUMO), dipole moment, softness (σ), chemical hardness (η), chemical potential (µ), ionization potential (IP), electron affinity (EA), nucleophilicity index (ω) and thermodynamics parameters.

Observations: The band gap reveals that compound A is hard, more thermodynamically stable and less labile than B. This is in agreement with the total energy, chemical hardness and chemical softness calculated for the compounds.

Result: The equilibrium constant calculation shows that the mixture of the tautomers in aqueous medium is 99.98 % and 0.12 % for compounds A and B respectively. This reveals that compound B is unstable in aqueous medium and is fast converted to compound A, this might explain the reason for compound B not to have been synthesized or reported in any literature.

Conclusion: Critical analysis of the charge population distributions shows that charge distribution responded more to the basis sets rather than the computational methods used for the calculations.

Keywords:

(Z)-Indol-3-ylidenemethanol, 1H-indole-3-carbaldehyde, DFT, dipole moment, hardness, molecular properties.

Affiliation:

Department of Pure and Applied Chemistry, Faculty of Pure and Applied Sciences, Ladoke Akintola University of Technology, Ogbomoso, Department of Pure and Applied Chemistry, Faculty of Pure and Applied Sciences, Ladoke Akintola University of Technology, Ogbomoso, Department of Pure and Applied Chemistry, Faculty of Pure and Applied Sciences, Ladoke Akintola University of Technology, Ogbomoso

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