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Exploration of Noncovalent Interactions, Chemical Reactivity, and Nonlinear Optical Properties of Piperidone Derivatives: A Concise Theoretical Approach

Exploration of Noncovalent Interactions, Chemical Reactivity, and Nonlinear Optical Properties of Piperidone Derivatives: A Concise Theoretical Approach

Authors :
Sumreen Asim
Akbar Ali
Shehbaz Ali
Muhammad Khalid
Naseeb Ahmad
Muhammad Usman Khan
Muhammad Saleem
Muhammad Mustaqeem
Muhammad Fayyaz ur Rehman
Source :
ACS Omega, Vol 5, Iss 22, Pp 13236-13249 (2020), ACS Omega
Publication Year :
2020
Publisher :
American Chemical Society, 2020.

Abstract

The organic compounds with a π-bond system lead to electric charge delocalization which enables them to reveal fascinating nonlinear optical properties. Mono-carbonyl curcuminoids also have an appealing skeleton from the conjugation view point. Interesting chemical structures of the 3,5-bis(arylidene)-N-benzenesulfonyl-4-piperidone derivatives motivated us to perform density functional theory (DFT)-based studies. Therefore, computations using the B3LYP/6-311G(d,p) functional of DFT were executed to explore geometric parameters, highest occupied molecular orbital (HOMO)–lowest unoccupied molecular orbital (LUMO) energies, and natural bond orbital (NBO) analyses. Moreover, three different functionals such as HF, B3LYP, and M06 with the 6-311G(d,p) basis set were used to investigate the average polarizability ⟨α⟩ and first hyperpolarizability (βtot)-based properties of all compounds. A good concurrence among calculated and experimental parameters was obtained through root mean square error calculations. The molecular stability of piperidone derivatives was examined using the Hirshfeld surface and NBO analyses. Natural population analysis was also performed to obtain insights about atomic charges. Calculated HOMO–LUMO energies showed that charge transfer interactions take place within the molecules. Moreover, global reactivity parameters including electronegativity, chemical hardness, softness, ionization potential, and electrophilicity were calculated using the HOMO and LUMO energies. The average polarizability ⟨α⟩ and first hyperpolarizability (βtot) values of all compounds were observed to be larger in magnitude at the aforesaid functional than the standard compound.

Details

Language :
English
ISSN :
24701343
Volume :
5
Issue :
22
Database :
OpenAIRE
Journal :
ACS Omega
Accession number :
edsair.doi.dedup.....b344f515c0af3ac7343c00b57ad487fe