European Journal of Chemistry

Comparative study of 4-((4-aminophenyl)diazenyl)-2-((2-phenylhydrazono)methyl)phenol and N-(4-((4-hydroxy-3-((2-phenylhydrazono)methyl)phenyl)diazenyl)phenyl)acetamide - DFT method

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Published: Mar 31, 2024
DOI: https://doi.org/10.5155/eurjchem.15.1.50-70.2498
Keywords:
NBO, HOMO-LUMO, Solvent effect, UV-Vis studies, Dihedral angle, Dipole moment
Section
Research Article
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Vol. 15 No. 1 (2024): March 2024
Dates
Received 2023-10-31
Accepted 2023-11-28
Published 2024-03-31
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Richard Rajkumar Siluvairaj
Department of Chemistry, St. Joseph’s College of Arts and Science, Cuddalore-607001, Tamilnadu, India
https://orcid.org/0000-0002-0064-8603
Vallal Perumal Govindasamy
Department of Chemistry, Annamalai University, Annamalainagar-608002, Tamilnadu, India
https://orcid.org/0009-0003-4479-6928
Rajarajan Govindasamy
Department of Chemistry, Annamalai University, Annamalainagar-608002, Tamilnadu, India
https://orcid.org/0000-0002-4186-189X
Periyanayagasamy Vanathu Chinnappan
Department of Chemistry, St. Joseph’s College of Arts and Science, Cuddalore-607001, Tamilnadu, India
https://orcid.org/0009-0000-5370-1263
Thanikachalam Venugopal
Department of Chemistry, Annamalai University, Annamalainagar-608002, Tamilnadu, India
https://orcid.org/0000-0003-1076-6272

Abstract

Theoretical calculation of 4-((4-aminophenyl)diazenyl)-2-((2-phenylhydrazono)methyl) phenol (1) and N-(4-((4-hydroxy-3-((2-phenylhydrazono)methyl)phenyl)diazenyl)phenyl) acetamide (2) was studied by DFT/B3LYP/6-311+G(d,p) basis set. The calculated values of geometric structural parameters, Fourier transform infrared spectral data, highest occupied molecular orbital and lowest unoccupied molecular orbital, natural bond orbital, nucleus-independent chemical shifts, Fukui function, polarizability, hyperpolarizability, and UV data of compounds 1 and 2 clearly indicate that substitution of the amino group alters the physical properties of compound 2. The nucleus-independent chemical shift values of the amino-substituted phenyl ring reduces the aromatic character due to the lone pair electron on nitrogen involved in inductive and conjunction effects, as well as due to OH, NH2 and OH, NHCOCH3 in compounds 1 and 2, respectively. The effect of the solvent on different parameters was studied, and it was found that increasing the dielectric constant increased the parameter studied. The stability and planarity of the molecule’s effects on dipole moment, energy, polarizability, and hyperpolarizability were studied extensively.


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Siluvairaj, R. R.; Govindasamy, V. P.; Govindasamy, R.; Chinnappan, P. V.; Venugopal, T. Comparative Study of 4-(4-aminophenyl)diazenyl)-2-(2-phenylhydrazono)methyl)phenol and N-(4-(4-Hydroxy-3-(2-phenylhydrazono)methyl)phenyl)diazenyl)phenyl)acetamide - DFT Method. Eur. J. Chem. 2024, 15, 50-70.

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