European Journal of Chemistry 2021, 12(4), 459-468 | doi: https://doi.org/10.5155/eurjchem.12.4.459-468.2160 | Get rights and content

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X-ray diffraction and Density Functional Theory based structural analyses of 2-phenyl-4-(prop-2-yn-1-yl)-1,2,4-triazolone


Shilpa Mallappa Somagond (1) orcid , Ahmedraza Mavazzan (2) orcid , Suresh Fakkirappa Madar (3) orcid , Madivalagouda Sannaikar (4) orcid , Shankar Madan Kumar (5) orcid , Sanjeev Ramchandra Inamdar (6) orcid , Aravind Raviraj Nesaragi (7) orcid , Jagadeesh Prasad Dasappa (8) orcid , Ravindra Ramappa Kamble (9,*) orcid

(1) Department of Chemistry, Karnatak University, Dharwad, 580003, India
(2) Department of Chemistry, Karnatak University, Dharwad, 580003, India
(3) Department of Chemistry, Karnatak University, Dharwad, 580003, India
(4) Department of Physics, Karnatak University, Dharwad, 580003, India
(5) Department of Chemistry and Molecular Biology, University of Gothenburg, Gothenburg, 9C 41390, Sweden
(6) Department of Physics, Karnatak University, Dharwad, 580003, India
(7) Department of Chemistry, Karnatak University, Dharwad, 580003, India
(8) Department of Materials Science, Mangalore University, Mangalagangothri, 574199, India
(9) Department of Chemistry, Karnatak University, Dharwad, 580003, India
(*) Corresponding Author

Received: 26 Jul 2021 | Revised: 26 Aug 2021 | Accepted: 23 Oct 2021 | Published: 31 Dec 2021 | Issue Date: December 2021

Abstract


This study is composed of X-ray diffraction and Density Functional Theory (DFT) based molecular structural analyses of 2-phenyl-4-(prop-2-yn-1-yl)-2,4-dihydro-3H-1,2,4-triazol-3-one (2PPT). Crystal data for C11H9N3O: Monoclinic, space group P21/c (no. 14), a = 7.8975(2) Å, b = 11.6546(4) Å, c = 11.0648(3) Å, β = 105.212(2)°, = 982.74(5) Å3, Z = 4, T = 296.15 K, μ(MoKα) = 0.091 mm-1, Dcalc = 1.346 g/cm3, 13460 reflections measured (5.174° ≤ 2Θ ≤ 64.72°), 3477 unique (Rint = 0.0314, Rsigma = 0.0298) which were used in all calculations. The final R1 was 0.0470 (I > 2σ(I)) and wR2 was 0.1368 (all data). The experimentally determined data was supported by theoretically optimized calculations processed with the help of Hartree-Fock (HF) technique and Density Functional Theory with the 6-311G(d,p) basis set in the ground state. Geometrical parameters (Bond lengths and angles) as well as spectroscopic (FT-IR, 1H NMR, and 13C NMR) properties of 2PPT molecule has been optimized theoretically and compared with the experimentally obtained results. Hirshfeld surface analysis with 2D fingerprinting plots was used to figure out the possible and most significant intermolecular interactions. The electronic characterizations such as molecular electrostatic potential map (MEP) and Frontier molecular orbital (FMO) energies have been studied by DFT/B3LYP approach. The MEP imparted the detailed information regarding electronegative and electropositive regions across the molecule. The HOMO-LUMO energy gap as high as 5.3601 eV was found to be responsible for the high kinetic stability of the 2PPT.


Keywords


N-Arylsydnone; 1,2,4-Triazolone; X-ray diffraction; Density functional theory; Hirshfeld surface analysis; Molecular electrostatic potential map

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DOI: 10.5155/eurjchem.12.4.459-468.2160

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University Grants Commission [F. No. 14-3/2012(NS/PE) Dated: 14-03-2012] , New Delhi, India.

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How to cite


Somagond, S.; Mavazzan, A.; Madar, S.; Sannaikar, M.; Kumar, S.; Inamdar, S.; Nesaragi, A.; Dasappa, J.; Kamble, R. Eur. J. Chem. 2021, 12(4), 459-468. doi:10.5155/eurjchem.12.4.459-468.2160
Somagond, S.; Mavazzan, A.; Madar, S.; Sannaikar, M.; Kumar, S.; Inamdar, S.; Nesaragi, A.; Dasappa, J.; Kamble, R. X-ray diffraction and Density Functional Theory based structural analyses of 2-phenyl-4-(prop-2-yn-1-yl)-1,2,4-triazolone. Eur. J. Chem. 2021, 12(4), 459-468. doi:10.5155/eurjchem.12.4.459-468.2160
Somagond, S., Mavazzan, A., Madar, S., Sannaikar, M., Kumar, S., Inamdar, S., Nesaragi, A., Dasappa, J., & Kamble, R. (2021). X-ray diffraction and Density Functional Theory based structural analyses of 2-phenyl-4-(prop-2-yn-1-yl)-1,2,4-triazolone. European Journal of Chemistry, 12(4), 459-468. doi:10.5155/eurjchem.12.4.459-468.2160
Somagond, Shilpa, Ahmedraza Mavazzan, Suresh Fakkirappa Madar, Madivalagouda Sannaikar, Shankar Madan Kumar, Sanjeev Ramchandra Inamdar, Aravind Raviraj Nesaragi, Jagadeesh Prasad Dasappa, & Ravindra Ramappa Kamble. "X-ray diffraction and Density Functional Theory based structural analyses of 2-phenyl-4-(prop-2-yn-1-yl)-1,2,4-triazolone." European Journal of Chemistry [Online], 12.4 (2021): 459-468. Web. 2 Oct. 2022
Somagond, Shilpa, Mavazzan, Ahmedraza, Madar, Suresh, Sannaikar, Madivalagouda, Kumar, Shankar, Inamdar, Sanjeev, Nesaragi, Aravind, Dasappa, Jagadeesh, AND Kamble, Ravindra. "X-ray diffraction and Density Functional Theory based structural analyses of 2-phenyl-4-(prop-2-yn-1-yl)-1,2,4-triazolone" European Journal of Chemistry [Online], Volume 12 Number 4 (31 December 2021)

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