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

Issue cover




Crossmark

  Open Access OPEN ACCESS | Open Access PEER-REVIEWED | RESEARCH ARTICLE | DOWNLOAD PDF | VIEW FULL-TEXT PDF | TOTAL VIEWS

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)°, V = 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.


Announcements


One of our sponsors will cover the article processing fee for all submissions made between May 17, 2023 and May 31, 2023 (Voucher code: SPONSOR2023).

Editor-in-Chief
European Journal of Chemistry

Keywords


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

Full Text:

PDF
PDF    Open Access

DOI: 10.5155/eurjchem.12.4.459-468.2160

Links for Article


| | | | | | |

| | | | | | |

| | | |

Related Articles




Article Metrics

icon graph This Abstract was viewed 392 times | icon graph PDF Article downloaded 125 times

Funding information


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

References


[1]. Liu, J.; Liu, Q.; Yang, X.; Xu, S.; Zhang, H.; Bai, R.; Yao, H.; Jiang, J.; Shen, M.; Wu, X.; Xu, J. Bioorg. Med. Chem. 2013, 21 (24), 7742-7751.
https://doi.org/10.1016/j.bmc.2013.10.017

[2]. Somagond, S. M.; Kamble, R. R.; Kattimani, P. P.; Joshi, S. D.; Dixit, S. R. Heterocycl. Comm. 2017, 23 (4), 317-324.
https://doi.org/10.1515/hc-2016-0073

[3]. Chandna, N.; Kapoor, J. K.; Grover, J.; Bairwa, K.; Goyal, V.; Jachak, S. M. New J. Chem. 2014, 38 (8), 3662-3672.
https://doi.org/10.1039/C4NJ00226A

[4]. Nesaragi, A. R.; Kamble, R. R.; Bayannavar, P. K.; Shaikh, S. K. J.; Hoolageri, S. R.; Kodasi, B.; Joshi, S. D.; Kumbar, V. M. Bioorg. Med. Chem. Lett. 2021, 41 (127984), 127984.
https://doi.org/10.1016/j.bmcl.2021.127984

[5]. Shaikh, S. K. J.; Sannaikar, M. S.; Kumbar, M. N.; Bayannavar, P. K.; Kamble, R. R.; Inamdar, S. R.; Joshi, S. D. ChemistrySelect 2018, 3 (16), 4448-4462.
https://doi.org/10.1002/slct.201702596

[6]. Liang, L.; Astruc, D. Coord. Chem. Rev. 2011, 255 (23-24), 2933-2945.
https://doi.org/10.1016/j.ccr.2011.06.028

[7]. Gimadiev, T. R.; Klimchuk, O.; Nugmanov, R. I.; Madzhidov, T. I.; Varnek, A. J. Mol. Struct. 2019, 1198 (126897), 126897.
https://doi.org/10.1016/j.molstruc.2019.126897

[8]. Popov, S. A.; Romanenko, G. V.; Reznikov, V. A. J. Mol. Struct. 2008, 872 (1), 30-39.
https://doi.org/10.1016/j.molstruc.2007.02.015

[9]. Naveen; Tittal, R. K.; Ghule, V. D.; Kumar, N.; Kumar, L.; Lal, K.; Kumar, A. J. Mol. Struct. 2020, 1209 (127951), 127951.
https://doi.org/10.1016/j.molstruc.2020.127951

[10]. Larsen, J. S.; Zahran, M. A.; Pedersen, E. B.; Nielsen, C. Monatsh. Chem. 1999, 130 (9), 1167-1173.
https://doi.org/10.1007/PL00010295

[11]. Cohen, A. J.; Mori-Sánchez, P.; Yang, W. Chem. Rev. 2012, 112 (1), 289-320.
https://doi.org/10.1021/cr200107z

[12]. Jones, R. O. Rev. Mod. Phys. 2015, 87, 897-923.
https://doi.org/10.1103/RevModPhys.87.897

[13]. Hostaš, J.; Řezáč, J. J. Chem. Theory Comput. 2017, 13 (8), 3575-3585.
https://doi.org/10.1021/acs.jctc.7b00365

[14]. Kohn, W. Rev. Mod. Phys. 1999, 71 (5), 1253-1266.
https://doi.org/10.1103/RevModPhys.71.1253

[15]. Bayannavar, P. K.; Sannaikar, M. S.; Madan Kumar, S.; Inamdar, S. R.; Shaikh, S. K. J.; Nesaragi, A. R.; Kamble, R. R. J. Mol. Struct. 2019, 1179, 809-819.

[16]. Kattimani, P. P.; Kamble, R. R.; Dorababu, A.; Hunnur, R. K.; Kamble, A. A.; Devarajegowda, H. C. J. Heterocycl. Chem. 2017, 54 (4), 2258-2265.

[17]. Somagond, S. M.; Wari, M. N.; Shaikh, S. K. J.; Inamdar, S. R.; Shankar, M. K.; Prasad, D. J.; Kamble, R. R. Eur. J. Chem. 2019, 10 (4), 281-294.
https://doi.org/10.5155/eurjchem.10.4.281-294.1844

[18]. Sheldrick, G. M. Acta Crystallogr. A 2008, 64 (Pt 1), 112-122.
https://doi.org/10.1107/S0108767307043930

[19]. Spek, A. L. Acta Crystallogr. A 1990, 46 (s1), 34-34.
https://doi.org/10.1111/j.1399-6576.1990.tb03209.x

[20]. Macrae, C. F.; Bruno, I. J.; Chisholm, J. A.; Edgington, P. R.; McCabe, P.; Pidcock, E.; Rodriguez-Monge, L.; Taylor, R.; van de Streek, J.; Wood, P. A. J. Appl. Crystallogr. 2008, 41 (2), 466-470.
https://doi.org/10.1107/S0021889807067908

[21]. Domingo, L. R.; Aurell, M. J.; Pérez, P.; Contreras, R. J. Phys. Chem. A 2002, 106 (29), 6871-6875.
https://doi.org/10.1021/jp020715j

[22]. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B Condens. Matter 1988, 37 (2), 785-789.
https://doi.org/10.1103/PhysRevB.37.785

[23]. Petersson, G. A.; Al-Laham, M. A. J. Chem. Phys. 1991, 94 (9), 6081-6090.
https://doi.org/10.1063/1.460447

[24]. Ditchfield, R. J. Chem. Phys. 1972, 56 (11), 5688-5691.
https://doi.org/10.1063/1.1677088

[25]. Wolinski, K.; Hinton, J. F.; Pulay, P. J. Am. Chem. Soc. 1990, 112 (23), 8251-8260.
https://doi.org/10.1021/ja00179a005

[26]. Spackman, P. R., Turner, M. J., McKinnon, J. J., Wolff, S. K., Grimwood, D. J., Jayatilaka, D.; Spackman, M. A. J. Appl. Cryst. 2021, 54 (3), 1006-1011.
https://doi.org/10.1107/S1600576721002910

[27]. Spackman, M. A.; Jayatilaka, D. CrystEngComm 2009, 11 (1), 19-32.
https://doi.org/10.1039/B818330A

[28]. Turner, M. J.; McKinnon, J. J.; Jayatilaka, D.; Spackman, M. A. CrystEngComm 2011, 13 (6), 1804-1813.
https://doi.org/10.1039/C0CE00683A

[29]. Kumbar, M. N.; Kamble, R. R.; Dasappa, J. P.; Bayannavar, P. K.; Khamees, H. A.; Mahendra, M.; Joshi, S. D.; Dodamani, S.; Rasal, V. P.; Jalalpure, S. J. Mol. Struct. 2018, 1160, 63-72.
https://doi.org/10.1016/j.molstruc.2018.01.047

[30]. Glusker, J. P.; Lewis, M.; Rossi, M. Crystal Structure Analysis for Chemists and Biologists. VCH Publishers New York. 1994, ISBN 0-89573-273-4.

[31]. Şen, B.; Sevincek, R.; Beksultanova, N.; Dogan, Ö. J. Mol. Struct. 2018, 1173, 33-41.
https://doi.org/10.1016/j.molstruc.2018.06.085

[32]. Panini, P.; Mohan, T. P.; Gangwar, U.; Sankolli, R.; Chopra, D. CrystEngComm 2013, 15 (22), 4549-4564.
https://doi.org/10.1039/c3ce40278a

[33]. Sathish, M.; Meenakshi, G.; Xavier, S.; Sebastian, S.; Periandy, S.; Ahmad, N.; Jamalis, J.; Rosli, M.; Fun, H.-K. J. Mol. Struct. 2018, 1164, 420-437.
https://doi.org/10.1016/j.molstruc.2018.03.004

[34]. McKinnon, J. J.; Jayatilaka, D.; Spackman, M. A. Chem. Commun. (Camb.) 2007, No. 37, 3814-3816.
https://doi.org/10.1039/b704980c

[35]. Spackman, M. A.; McKinnon, J. J. CrystEngComm 2002, 4 (66), 378-392.
https://doi.org/10.1039/B203191B

[36]. Singh, R. N.; Kumar, A.; Tiwari, R. K.; Rawat, P. Spectrochim. Acta A Mol. Biomol. Spectrosc. 2013, 113, 378-385.
https://doi.org/10.1016/j.saa.2013.04.121

[37]. Sjoberg, P.; Politzer, P. J. Phys. Chem. 1990, 94 (10), 3959-3961.
https://doi.org/10.1021/j100373a017

[38]. Lee, B.; Richards, F. M. J. Mol. Biol. 1971, 55 (3), 379-400.
https://doi.org/10.1016/0022-2836(71)90324-X

[39]. Weiner, P. K.; Langridge, R.; Blaney, J. M.; Schaefer, R.; Kollman, P. A. Proc. Natl. Acad. Sci. U. S. A. 1982, 79 (12), 3754-3758.
https://doi.org/10.1073/pnas.79.12.3754

[40]. Connolly, M. L. Science 1983, 221 (4612), 709-713.
https://doi.org/10.1126/science.6879170

[41]. Francl, M. M.; Hout, R. F., Jr; Hehre, W. J. J. Am. Chem. Soc. 1984, 106 (3), 563-570.
https://doi.org/10.1021/ja00315a018

[42]. Arteca, G. A.; Jammal, V. B.; Mezey, P. G.; Yadav, J. S.; Hermsmeier, M. A.; Gund, T. M. J. Mol. Graph. 1988, 6 (1), 45-53.
https://doi.org/10.1016/0263-7855(88)80061-4

[43]. Dunitz, J. D.; Filippini, G.; Gavezzotti, A. Tetrahedron 2000, 56 (36), 6595-6601.
https://doi.org/10.1016/S0040-4020(00)00460-9

[44]. Bondi, A. Van Der Waals Volumes and Radii. J. Phys. Chem. 1964, 68 (3), 441-451.
https://doi.org/10.1021/j100785a001

[45]. Vasanthakumari, R.; Nirmala, W.; Sagadevan, S.; Mugeshini, S.; Rajeswari, N.; Balu, R.; Santhakumari, R. J. Mol. Struct. 2021, 1239 (130449), 130449.
https://doi.org/10.1016/j.molstruc.2021.130449

[46]. Naresh, P.; Pramodh, B.; Naveen, S.; Ganguly, S.; Panda, J.; Sunitha, K.; Maniukiewicz, W.; Lokanath, N. K. J. Mol. Struct. 2021, 1236 (130228), 130228.
https://doi.org/10.1016/j.molstruc.2021.130228


Supporting information


The Supplementary Material for this article can be found online at: Supplementary files

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. 30 May. 2023
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)

The other citation formats (EndNote | Reference Manager | ProCite | BibTeX | RefWorks) for this article can be found online at: How to cite item



DOI Link: https://doi.org/10.5155/eurjchem.12.4.459-468.2160


CrossRef | Scilit | GrowKudos | Researchgate | Publons | ScienceGate | Scite | Lens | OUCI

WorldCat Paperbuzz | LibKey Citeas | Dimensions | Semanticscholar | Plumx | Kopernio | Zotero | Mendeley

ZoteroSave to Zotero MendeleySave to Mendeley



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

Refbacks

  • There are currently no refbacks.


Bookmark and Share


Copyright (c) 2021 Authors

Creative Commons License
This work is published and licensed by Atlanta Publishing House LLC, Atlanta, GA, USA. The full terms of this license are available at http://www.eurjchem.com/index.php/eurjchem/pages/view/terms and incorporate the Creative Commons Attribution-Non Commercial (CC BY NC) (International, v4.0) License (http://creativecommons.org/licenses/by-nc/4.0). By accessing the work, you hereby accept the Terms. This is an open access article distributed under the terms and conditions of the CC BY NC License, which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited without any further permission from Atlanta Publishing House LLC (European Journal of Chemistry). No use, distribution or reproduction is permitted which does not comply with these terms. Permissions for commercial use of this work beyond the scope of the License (http://www.eurjchem.com/index.php/eurjchem/pages/view/terms) are administered by Atlanta Publishing House LLC (European Journal of Chemistry).


© Copyright 2010 - 2023 • Atlanta Publishing House LLC • All Right Reserved.

The opinions expressed in all articles published in European Journal of Chemistry are those of the specific author(s), and do not necessarily reflect the views of Atlanta Publishing House LLC, or European Journal of Chemistry, or any of its employees.

Copyright 2010-2023 Atlanta Publishing House LLC. All rights reserved. This site is owned and operated by Atlanta Publishing House LLC whose registered office is 2850 Smith Ridge Trce Peachtree Cor GA 30071-2636, USA. Registered in USA.