Journal of Molecular Structure, volume 1270, pages 133997
Synthesis, conformational study and DFT analysis of novel nonlinear optically active 2r,6c-diaryl-3t-methylpiperidin-4-one N-(2′-furoyl)hydrazones
Publication type: Journal Article
Publication date: 2022-12-01
Journal:
Journal of Molecular Structure
Quartile SCImago
Q2
Quartile WOS
Q2
Impact factor: 3.8
ISSN: 00222860
Organic Chemistry
Inorganic Chemistry
Spectroscopy
Analytical Chemistry
Abstract
• A new series of hydrazones were synthesized efficiently. • The piperidine core of all the targeted hydrazones adopted the chair conformation. • Hydrazones showed superior NLO property than the reference material urea. • Global reactivity parameters indicated reasonable stability and more reactivity. A series of nonlinear optical (NLO) active 2-furoic acid hydrazide derivatives, 2r,6c-diaryl-3t-methylpiperidin-4-one N -(2′-furoyl)hydrazones ( 6–10 ), were synthesized. The structures of these hydrazones were confirmed unambiguously by Fourier transform infrared spectroscopy, mass spectrometry, elemental analysis, 1 H, 13 C, HOMO-COSY, HSQC, and HMBC nuclear magnetic resonance spectroscopy. The piperidine core of all the targeted hydrazones ( 6–10 ) adopted the chair conformation with the equatorial orientations of all the substituents and the ‘ E ’ configuration about the C=N bond observed. Density functional theory using the B3LYP/6–31G(d,p) level of theory indicated that all hydrazones favor the ‘ E ’ isomer state. The Mulliken population, frontier molecular orbitals (FMO), molecular electrostatic potential (MEP) surfaces, and reactivity parameters were also evaluated and showed a good correlation with the experimental data. The efficiency of hydrazones ( 6–10 ) in terms of the nonlinear optical (NLO) activity was proven, and the hydrazones ( 6–10 ) showed higher NLO activity compared to that of the reference molecule, as determined by the molecular hyperpolarizability measurements. The structural, spectral, and electrochemical properties were also determined, and DFT analysis was consistent with the experimental outcomes. The FMO, MEP, and reactivity parameter analyses revealed intramolecular charge transfer and high reactive features, leading to superior NLO property of hydrazones ( 6–10 ).
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Citations by publishers
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Meenatchi V., Soo Han S. Synthesis, conformational study and DFT analysis of novel nonlinear optically active 2r,6c-diaryl-3t-methylpiperidin-4-one N-(2′-furoyl)hydrazones // Journal of Molecular Structure. 2022. Vol. 1270. p. 133997.
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Meenatchi V., Soo Han S. Synthesis, conformational study and DFT analysis of novel nonlinear optically active 2r,6c-diaryl-3t-methylpiperidin-4-one N-(2′-furoyl)hydrazones // Journal of Molecular Structure. 2022. Vol. 1270. p. 133997.
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TY - JOUR
DO - 10.1016/j.molstruc.2022.133997
UR - https://doi.org/10.1016/j.molstruc.2022.133997
TI - Synthesis, conformational study and DFT analysis of novel nonlinear optically active 2r,6c-diaryl-3t-methylpiperidin-4-one N-(2′-furoyl)hydrazones
T2 - Journal of Molecular Structure
AU - Meenatchi, Venkatasamy
AU - Soo Han, Sung
PY - 2022
DA - 2022/12/01
PB - Elsevier
SP - 133997
VL - 1270
SN - 0022-2860
ER -
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@article{2022_Meenatchi,
author = {Venkatasamy Meenatchi and Sung Soo Han},
title = {Synthesis, conformational study and DFT analysis of novel nonlinear optically active 2r,6c-diaryl-3t-methylpiperidin-4-one N-(2′-furoyl)hydrazones},
journal = {Journal of Molecular Structure},
year = {2022},
volume = {1270},
publisher = {Elsevier},
month = {dec},
url = {https://doi.org/10.1016/j.molstruc.2022.133997},
pages = {133997},
doi = {10.1016/j.molstruc.2022.133997}
}