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5-Methyl-4-[3-(2-oxopyrrolidin-1-yl)propyl]-2,4-dihydro-3H-1,2,4-triazol-3-one: Synthesis, Characterization, and DFT Study

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Abstract

5-Methyl-4-(3-(2-oxopyrrolidin-1-yl)propyl)-2,4-dihydro-3H-1,2,4-triazol-3-one was synthesized and characterized by X-ray, FTIR and NMR spectroscopic techniques. The molecular geometry and spectral parameters of the title compound were also computed by the DFT/B3LYP76-311++G(d,p) method, and the theoretical data showed a good agreement with the experimental ones. The differences between the theoretical and experimental IR and NMR spectra supported the presence of inter- and intramolecular C-H⋯O and intermolecular N-H⋯O hydrogen bonds, which were revealed by X-ray analysis. Nonlinear optical (NLO) properties of the title compound were analyzed by the DFT/B3LYP/6-311++G(d,p) method by calculating the mean polarizability (α) and first-order hyperpolarizability values (β) (α = 22.0746454×10−24, β = 10.1110649×10−31 esu). As compared with the corresponding data for urea (α = 4.9067×10−24, β = 7.8782×10−31 esu), these values suggest promising NLO properties.

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Authors and Affiliations

  1. Vocational School of Technical Sciences, Gazi University, Ostim, Ankara, 06374, Turkey

    N. Süleymanoğlu

  2. Department of Mathematics and Science Education, Educational Faculty, Ondokuz Mayıs University, Kurupelit, Samsun, 55139, Turkey

    R. Ustabaş

  3. Department of Chemistry, Faculty of Sciences, Karadeniz Technical University, Trabzon, 61080, Turkey

    Y. Ünver

  4. Department of Physics, Faculty of Arts and Science, Giresun University, Giresun, 28100, Turkey

    Y. B. Alpaslan

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  1. N. Süleymanoğlu
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  2. R. Ustabaş
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  3. Y. Ünver
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  4. Y. B. Alpaslan
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Correspondence to N. Süleymanoğlu or Y. Ünver.

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Süleymanoğlu, N., Ustabaş, R., Ünver, Y. et al. 5-Methyl-4-[3-(2-oxopyrrolidin-1-yl)propyl]-2,4-dihydro-3H-1,2,4-triazol-3-one: Synthesis, Characterization, and DFT Study. Russ J Org Chem 55, 1929–1935 (2019). https://doi.org/10.1134/S1070428019120200

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