A computational study on molecular structure and stability of tautomers of dipyrrole-based phenanthroline analogue

Meshhal, Moyassar; Shibl, Mohamed F.; El‐Demerdash, Safinaz H.; El‐Nahas, Ahmed M.

doi:10.1016/j.comptc.2018.10.003

Cited by 3 publications

(2 citation statements)

References 33 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…108 For the investigated systems, NICS zz and HOMA calculations were performed at the B3LYP/6-31G(d,p) level in the gas and ethanol to evaluate the aromatic character of each ring are presented in Table 4. Apparently, the NICS and HOMA , 111 azulene, 34,112,113 and azaazulene 114 and also can support the order of stability. Both NICS(1) zz and HOMA indices show good performance with the relative energies of enol and keto tautomers.…”

Section: Introductionmentioning

confidence: 93%

Structures, Energetics, and Spectra of (NH) and (OH) Tautomers of 2-(2-Hydroxyphenyl)-1-azaazulene: A Density Functional Theory/Time-Dependent Density Functional Theory Study

et al. 2022

Self Cite

View full text Add to dashboard Cite

Tautomerization of 2-(2-hydroxyphenyl)-1-azaazulene ( 2OHPhAZ ) in the gas phase and ethanol has been studied using B3LYP, M06-2X, and ωB97XD density functional theory (DFT) with different basis sets. For more accurate data, energies were refined at CCSD(T)/6-311++G(2d,2p) in the gas phase. Nuclear magnetic resonance (NMR), aromaticity, Fukui functions, acidity, and basicity were also calculated and compared with experimental data. Time-dependent density functional theory (TDDFT)-solvation model based on density (TDDFT-SMD) calculations in acetonitrile have been utilized for the simulation of UV–vis electronic spectra. In addition, electronic structures of the investigated system have been discussed. The results reveal that the enol form ( 2OHPhAZ ) is thermodynamically and kinetically stable relative to the keto tautomer ( 2OPhAZ ) and different rotamers ( 2OHPhAZ–R1:R3 ) in the gas phase and ethanol. A comparison with the experiment illustrates a good agreement and supports the computational findings.

show abstract

Section: Introductionmentioning

confidence: 93%

Structures, Energetics, and Spectra of (NH) and (OH) Tautomers of 2-(2-Hydroxyphenyl)-1-azaazulene: A Density Functional Theory/Time-Dependent Density Functional Theory Study

et al. 2022

Self Cite

View full text Add to dashboard Cite

show abstract

“…In the investigated NB system, NICSzz and HOMA calculation were performed at the B3LYP/6-311 + G(d,p) level provide a good match with previous studies on pyrrole [ [115] , [116] , [117] ]. During moving from first group to second group isomers, both NICS (1) zz and HOMA indices show good results with the decreasing order of aromaticity.…”

Section: Energies and Stabilitymentioning

confidence: 55%

Isosterism in pyrrole via azaboroles substitution, a theoretical investigation for electronic structural, stability and aromaticity

H. El-Demerdash,

F. Gad,

M. El-Mehasseb

et al. 2023

Heliyon

View full text Add to dashboard Cite

Solvent and temperature effects on the tautomerization of a carbonitrile molecule: A conductor-like polarizable continuum model (CPCM) study

Khanjari

Mohtat

Ghiasi

et al. 2021

MGC

View full text Add to dashboard Cite

This research examined the effects of solvent polarity and temperature on the tautomerization of a carbonitrile molecule at CAM-B3LYP/6-311G (d,p) level of theory. The selected solvents were n-hexane, diethyl ether, pyridine, ethanol, methanol, and water. The solvent effects were examined by the self-consistent reaction field theory (SCRF) based on conductor-like polarizable continuum model (CPCM). The solvent effects were explored on the energy barrier, frontier orbitals energies, and HOMO-LUMO gap. Dependencies of thermodynamic parameters (ΔG and ΔH) on the dielectric constants of solvents were also tested. Specifically, the temperature dependencies of the thermodynamics parameters were studied within 100–1000 K range. The rate constant of the tautomerism reaction was computed from 300 to 1200 K, in the gas phase.

show abstract

A computational study on molecular structure and stability of tautomers of dipyrrole-based phenanthroline analogue

Cited by 3 publications

References 33 publications

Structures, Energetics, and Spectra of (NH) and (OH) Tautomers of 2-(2-Hydroxyphenyl)-1-azaazulene: A Density Functional Theory/Time-Dependent Density Functional Theory Study

Structures, Energetics, and Spectra of (NH) and (OH) Tautomers of 2-(2-Hydroxyphenyl)-1-azaazulene: A Density Functional Theory/Time-Dependent Density Functional Theory Study

Isosterism in pyrrole via azaboroles substitution, a theoretical investigation for electronic structural, stability and aromaticity

Solvent and temperature effects on the tautomerization of a carbonitrile molecule: A conductor-like polarizable continuum model (CPCM) study

Contact Info

Product

Resources

About