Identifying and explaining the regioselectivity of alkylation of 1,2,4-triazole-3-thiones using NMR, GIAO and DFT methods

Fizer, Maksym; Slivka, Mikhailo; Korol, Nataliya; Fizer, Oksana

doi:10.1016/j.molstruc.2020.128973

Cited by 24 publications

(2 citation statements)

References 81 publications

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“…In this study, experimental values of DADC 1 H and 13 C NMR spectra have been compared by examining their theoretical spectroscopic properties. After the DADC structure was minimized with the Gaussian 09W program and the DFT / B3LYP / 6-311G and B3PW91/SDD method, 1 H shift values were calculated according to the GIAO method (Fizer et al 2021;Gancheff and Denis 2015). MS has been taken as reference in the calculations.…”

Section: H Nmr Spectrummentioning

confidence: 99%

Theoretical Investigation of 1H and 13C NMR Spectra of Diethanol Amine Dithiocarbamate RAFT Agent

GÖREN>¹,

BAĞLAN>²,

Čakmak

2022

Iğdır Üniversitesi Fen Bilimleri Enstitüsü Dergisi

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In this study, quantum chemical studies of diethanolamine dithiocarbamate (DADC) RAFT compound were carried out. For this purpose, the composite was optimized by using the DFT / B3LYP method 6-311G and the B3PW91 method SDD basis set. By using the optimized structure obtained according to the GIAO method, 1H and 13C NMR chemical shift values in the gas phase were calculated. According to the results obtained, it was seen that the theoretical data were coherent with the experimental data. In addition, in the theoretical part of the study, the FT-IR frequency values of the compound synthesized by using the same methods and basic set were compared experimentally and theoretically. In addition, the structure details and analysis of molecules, electronic properties such as HOMO and LUMO energies, molecular electrostatic potential (MEP) and thermodynamic properties have been performed. The electric dipole moment (μ) and the initial hyperpolarizability (β) values of the studied molecule were calculated by using ab initio quantum mechanical calculations. In addition, the calculated results show that the (DADC) molecule can have nonlinear optical (NLO) behavior with nonzero values. Neutral Band Orbital (NBO) analysis has been calculated with DFT / B3PW91/SDD basis set.

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Section: H Nmr Spectrummentioning

confidence: 99%

Theoretical Investigation of 1H and 13C NMR Spectra of Diethanol Amine Dithiocarbamate RAFT Agent

GÖREN>¹,

BAĞLAN>²,

Čakmak

2022

Iğdır Üniversitesi Fen Bilimleri Enstitüsü Dergisi

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“…Studies on drugs and biologically active compounds continue to attract the attention of researchers specializing in the field of heterocyclic chemistry and related scientific areas [4][5][6][7]. Heterocyclic molecules such as 1,2,4-triazoles lack natural analogs, yet research into the 1,2,4-triazole chemistry is quite popular because of the vast number of selective and direct synthetic pathways to these compounds [7][8][9] and the extensive range of derivatization techniques that are readily available [10][11][12][13][14]. The popularity of the 1,2,4-triazole scaffold is primarily due to its high biological activities [15], such as antifungal [15][16][17][18][19], antibacterial [20][21][22], antiviral [23], and anticancer [24], in addition to its chelating [25][26][27] abilities.…”

Section: Introductionmentioning

confidence: 99%

An efficient microwave‐assisted synthesis of novel quinolone–triazole and conazole–triazole hybrid derivatives as antimicrobial and anticancer agents

Cebeci

Ceylan

Karaoğlu

et al. 2022

Journal of Heterocyclic Chem

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1,2,4-Triazole-fluoroquinolone and 1,2,4-triazole-conazole hybrids are designed, synthesized, and investigated in vitro against a variety of common diseases. The structure of the newly synthesized compounds are characterized from spectral data (IR, 1 H NMR, 13 C NMR, and LC-MS). The antibacterial activity against both Gram-positive and Gram-negative bacteria is shown to be enhanced by many of the produced compounds. Also, some of the products are found to have strong antiproliferative effects aganist HeLa cervical cancer cells, whilst demonstrating cytotoxic effects toward normal cells.

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DFT Computation, Spectroscopic, Hirshfeld Surface, Docking and Topological Analysis on 2,2,5‐Trimethyl‐1,3‐Dioxane‐5‐Carboxylic Acid as Potent Anti‐Cancer Agent

kumar,

Karthik,

Sumathi

et al. 2024

Int J of Quantum Chemistry

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The 2,2,5‐trimethyl‐1,3‐dioxane‐5‐carboxylic acid (TDCA) using both theoretical and experimental methods have been studied. The sample has been subjected to XRD, FTIR, FT‐Raman, (C13 and H1) NMR, and UV–vis spectrum analysis. Then, theoretical calculations have been performed at the DFT/B3LYP/6‐311++G(d,p) higher based scale. The theoretical and experimental geometrical parameters and frequencies have been compared well. Theoretical and experimental NMR chemical shifts have been determined. Absorption wavelengths of UV–Vis spectrum were experimentally measured and compared with TD‐DFT predictions. Detailed explanations have been given for frontier molecular orbitals, low density gradient, distribution of Mulliken charges, molecular electrostatic potential (MEP), RDG, localized orbital location, and electron localized activities. Based on the studied 2D image of the Hirschfield surfaces, H···H (65.6%) and O···H/H···O (33.6%) are found as the controlling interactions. A high binding affinity of −6.5 Kcal/mol has been calculated against 4OAR protein. These theoretical findings of the molecule may be used as an anticancer drug candidate, which helps to explain the structural stability, reactivity and anticancer potential of TDCA. High drug affinity for the TDCA has been detected by in silico ADMET prediction.

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Identifying and explaining the regioselectivity of alkylation of 1,2,4-triazole-3-thiones using NMR, GIAO and DFT methods

Cited by 24 publications

References 81 publications

Theoretical Investigation of 1H and 13C NMR Spectra of Diethanol Amine Dithiocarbamate RAFT Agent

Theoretical Investigation of 1H and 13C NMR Spectra of Diethanol Amine Dithiocarbamate RAFT Agent

An efficient microwave‐assisted synthesis of novel quinolone–triazole and conazole–triazole hybrid derivatives as antimicrobial and anticancer agents

DFT Computation, Spectroscopic, Hirshfeld Surface, Docking and Topological Analysis on 2,2,5‐Trimethyl‐1,3‐Dioxane‐5‐Carboxylic Acid as Potent Anti‐Cancer Agent

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