Detailed analytical studies of 1,2,4-triazole derivatized quinoline

Shilpa Mallappa Somagond; Manjunath Ningappa Wari; Saba Kauser Jaweed Shaikh; Sanjeev Ramchandra Inamdar; Madan Kumar Shankar; Dasappa Jagadeesh Prasad; Ravindra Ramappa Kamble

doi:10.5155/eurjchem.10.4.281-294.1844

PDF CIF FILE

Published: Dec 31, 2019

DOI: https://doi.org/10.5155/eurjchem.10.4.281-294.1844

Keywords:

UV absorption, Hirshfeld surface, Cyclic voltammetry, Single crystal structure, Natural bond orbital (NBO), Time Dependent-Density Functional Theory

Section

Research Article

Issue

Vol. 10 No. 4 (2019): December 2019

Dates

Received 2019-03-07
Accepted 2019-07-09
Published 2019-12-31

Shilpa Mallappa Somagond

Department of Chemistry, Karnatak University, Dharwad, Karnataka 580003, India

http://orcid.org/0000-0002-0481-3426

Manjunath Ningappa Wari

Department of Physics, Karnatak University Dharwad, Karnataka 580003, India

http://orcid.org/0000-0003-0342-1284

Saba Kauser Jaweed Shaikh

Department of Chemistry, Karnatak University, Dharwad, Karnataka 580003, India

http://orcid.org/0000-0001-8839-9498

Sanjeev Ramchandra Inamdar

Department of Physics, Karnatak University Dharwad, Karnataka 580003, India

http://orcid.org/0000-0003-3398-4897

Madan Kumar Shankar

Department of Science and Technology, PURSE Laboratory, Mangalore University, Mangalagangothri, Karnataka 574199, India

http://orcid.org/0000-0002-7944-1081

Dasappa Jagadeesh Prasad

Department of Chemistry, Mangalore University, Konaje, Mangalore, Karnataka 574199, India

http://orcid.org/0000-0003-1333-028X

Ravindra Ramappa Kamble

Department of Chemistry, Karnatak University, Dharwad, Karnataka 580003, India

http://orcid.org/0000-0002-0384-655X

Abstract

The present study describes, the X-ray single crystal analysis of 4-((2-chloro-6-methoxyquinolin-3-yl)methyl)-2-phenyl-2H-1,2,4-triazol-3(4H)-one (TMQ). The crystal data for C₁₉H₁₅ClN₄O₂: monoclinic, space group P2₁/n (no. 14), a = 7.3314(15) Å, b = 12.459(3) Å, c = 18.948(4) Å, β = 98.322(9)°, V = 1712.5(6) Å³, Z = 4, T = 296.15 K, μ(MoKα) = 0.245 mm^-1, Dcalc = 1.423 g/cm³, 5082 reflections measured (3.926° ≤ 2Θ ≤ 38.556°), 1428 unique (R_int = 0.0545, R_sigma = 0.0574) which were used in all calculations. The final R₁ was 0.0423 (I >2σ(I)) and wR₂ was 0.1145 (all data). The Density functional theory optimized molecular geometries in TMQ agree closely with those obtained from crystallographic studies. The Highest Occupied Molecular Orbital (HOMO) and Lowest Unoccupied Molecular Orbital (LUMO) energy levels and energy gap were calculated by experimental (UV absorption & Cyclic voltammetry) and theoretical studies in two different solvents. The natural bond orbital analysis was performed to understand the molecular interaction on the basis of stability of molecule arising from hyper-conjugative interaction and charge delocalization. Hirshfeld surface and their related fingerprint plots enabled the identification of significant intermolecular interaction. The molecular electrostatic potential analysis provides the visual image of the chemically active sites and comparable reaction of atoms.

This Abstract was viewed 1602 times |

Article PDF downloaded 592 times

Article CIF FILE downloaded 0 times

How to Cite

(1)

Somagond, S. M.; Wari, M. N.; Shaikh, S. K. J.; Inamdar, S. R.; Shankar, M. K.; Prasad, D. J.; Kamble, R. R. Detailed Analytical Studies of 1,2,4-Triazole Derivatized Quinoline. Eur. J. Chem. 2019, 10, 281-294.

Links for Article

Crossref - Scopus - Google - European PMC

References

[1]. Rastelli, E. J.; Truong, N. T.; Coltart, D. M. Org. Lett. 2016, 18, 5588-5591.
https://doi.org/10.1021/acs.orglett.6b02825

[2]. Kim, S. H.; Kaplan, J. A.; Sun, Y.; Shieh, A.; Sun, H. L.; Croce, C. M.; Parquette, J. R. Chem. Eur. J. 2015, 21, 101-105.
https://doi.org/10.1002/chem.201404520

[3]. Forkuo, A. D.; Ansah, C.; Boadu, K. M.; Boampong, J. N.; Ameyaw, E. O.; Gyan, B. A.; Ofori, M. F. Malar. J. 2016, 15, 1-12.
https://doi.org/10.1186/s12936-016-1223-8

[4]. Gaurav, A.; Singh, R. Med. Chem. Res. 2014, 23, 5008-5030.
https://doi.org/10.1007/s00044-014-1048-3

[5]. Lee, H. W.; Lee, H. S.; Park, J. H.; Cheong, J. J.; Kwon, H. B.; Kim, K. O.; Song, H. H. J. Appl. Biol. Chem. 2015, 58, 1-3 .

[6]. Wise, R.; Andrews, J. M.; Edwards, L. J. Antimicrob. Agents. Chemother. 1983, 23, 559-564.
https://doi.org/10.1128/AAC.23.4.559

[7]. Brown, C. E.; Mc Nulty, J.; Bordon, C.; Yolken, R.; Jones-Brando, L. Org. Biomol. Chem. 2016, 14, 5951-5955.
https://doi.org/10.1039/C6OB01083K

[8]. Musiol, R.; Serda, M.; Hensel-Bielowka, S.; Polanski, J. Curr. Med. Chem. 2010, 17, 1960-1973.
https://doi.org/10.2174/092986710791163966

[9]. Luo, Z. G.; Zeng, C. C.; Wang, F.; He, H. Q.; Wang, C. X.; Du, H. G.; Hu, L. M. Chem. Res. Chin. Univ. 2009, 25, 841-845.

[10]. Liu, H.; Dong, Y.; Zhang, B.; Liu, F.; Tan, C.; Tan, Y.; Jiang, Y. Sensors Sens. Actuator B-Chem. 2016, 234, 616-624.
https://doi.org/10.1016/j.snb.2016.04.175

[11]. Prodi, L.; Bargossi, C.; Montalti, M.; Zaccheroni, N.; Su, N.; Bradshaw, J. S.; Izatt, R. M.; Savage, P. B. J. Am. Chem. Soc. 2000, 122, 6769-6770.
https://doi.org/10.1021/ja0006292

[12]. El Ashry, E. S. H.; Awad, L. F.; Soliman, S. M.; Moaty, M. N. A. A.; Ghabbour, H. A.; Barakat, A. J. Mol. Struct. 2017, 1146, 432-440.
https://doi.org/10.1016/j.molstruc.2017.06.002

[13]. Almasirad, A.; Tabatabai, S. A.; Faizi, M.; Kebriaeezadeh, A.; Mehrabi, N.; Dalvandi, A.; Shafiee, A. Bioorg. Med. Chem. Lett. 2004, 14, 6057-6059.
https://doi.org/10.1016/j.bmcl.2004.09.072

[14]. El Akri, K.; Bougrin, K.; Balzarini, J.; Faraj, A.; Benhida, R. Bioorg. Med. Chem. Lett. 2007, 17, 6656-6659.
https://doi.org/10.1016/j.bmcl.2007.08.077

[15]. Karthikeyan, M. S.; Holla, B. S.; Kumari, N. S. Eur. J. Med. Chem. 2008, 43, 309-314.
https://doi.org/10.1016/j.ejmech.2007.03.024

[16]. Somagond, S. M.; Kamble R. R.; Kattimani, P. P.; Shaikh, S. J.; Dixit, S. R.; Joshi, S. D.; Devarajegowda, H. C. Chemistry Select 2018, 3, 2004-2016.
https://doi.org/10.1002/slct.201702279

[17]. Yang, F.; Zhang, X. L.; Sun, K.; Xiong, M. J.; Xia, P. F.; Cao, Z. J. Synth. Met. 2008, 158, 988-992.
https://doi.org/10.1016/j.synthmet.2008.06.028

[18]. Maiti, A.; Svizhenko, A.; Anantram, M. P. Phys. Rev. Lett. 2002, 88, 1268051-1268054.
https://doi.org/10.1103/PhysRevLett.88.126805

[19]. Zhou, D.; Ma, D.; Wang, Y.; Xianchun Liu; Xinhe Bao; Chem. Phys. Lett. 2003, 373, 46-51.
https://doi.org/10.1016/S0009-2614(03)00513-X

[20]. Leconte, J.; Markovits, A.; Skalli, M. K.; Minot, C.; Belmajdoub, A. Surf. Sci. 2002, 497, 194-204.
https://doi.org/10.1016/S0039-6028(01)01477-7

[21]. Wang, J.; Liu, C.; Fang, Z.; Liu, Y.; Han, Z.; J. Phys. Chem. B 2004, 108, 1653-1659.
https://doi.org/10.1021/jp035779o

[22]. Koch, W.; Holthausen, M. C. A.; Chemists Guide to Density Functional Theory, Wiley-VCH, Weinheim, New York, Chichester, 2000.

[23]. Parr, R. G.; Yang, W. T.; Density-Functional Theory of Atoms and Molecules, Oxford University Press, New York, 1989.

[24]. Szafran, M.; Komasa, A.; Adamska, E. B. J. Mol. Struct. Theochem. 2007, 827, 101-107.
https://doi.org/10.1016/j.molstruc.2006.05.012

[25]. Rigaku, Crystal Clear SM Expert 2. 0 r15. Software for data collection and processing. Rigaku Corporation, Tokyo, Japan. 2011.

[26]. Sheldrick, G. M. Acta. Cryst. A 2008, 64, 112-122.
https://doi.org/10.1107/S0108767307043930

[27]. Spek, A. L. Acta. Cryst. A 1990, 46, C34.
https://doi.org/10.1107/S0108270189012850

[28]. Macrae, C. F.; Bruno, I. J.; Chisholm, J. A.; Edging-ton, P. R.; McCabe, P.; Pidcock, E.; Rodriguez-Monge, L.; Taylor, R.; van deStreek, J.; Wood, P. A. J. Appl. Crystallog. 2008, 41, 466-470.
https://doi.org/10.1107/S0021889807067908

[29]. McKinnon, J. J.; Spackman, M. A.; Mitchell, A. S.; J. Acta. Crystallogr. B 2004, 60, 627-668.
https://doi.org/10.1107/S0108768104020300

[30]. Spackman, M. A.; Jayatilaka, D. Cryst. Engg. Comm. 2009, 11, 19-32.
https://doi.org/10.1039/B818330A

[31]. Spackman, M. A.; McKinnon, J. J. Cryst. Eng. Comm. 2002, 4, 378-392.
https://doi.org/10.1039/B203191B

[32]. Madan, K. S.; Manjunath, B. C.; Lingaraju, G. S.; Abdoh, M. M. M.; Sadashiva, M. P.; Lokanath, N. K. Crystal. Struct. Theor. Appl. 2013, 3, 124-131.

[33]. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, J. M.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, O.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian, Inc., Gaussian 09, Revision B. 01, Wallingford CT, 2010.

[34]. Hartley, D.; Kidd, H. (Eds.), The Agrochemicals Handbook, Royal Society of Chemistry, Unwin Brothers Ltd., Old Woking Surrey, United Kingdom, 1983.

[35]. Gerhartz, W.; Ullmann's Encyclopedia of Industrial Chemistry, 5th ed., VCH Publishers, Deerfield Beach FL, 1985.

[36]. Glendening, E. D.; Reed, A. E.; Carpenter, J. E.; Weinhold, F.; NBO Version 3. 1, Gaussian Inc., Pittsburgh, PA, 2000-2003.

[37]. Dennington, R.; Keith T.; Millam J.; GaussView, Version 5, Semichem Inc., Shawnee Mission KS, 2009.

[38]. Mckinnon, J. J.; Mitchell, A. S.; Spackman, M. A. Chem. Eur. J. 1998, 4, 2136-2144.
https://doi.org/10.1002/(SICI)1521-3765(19981102)4:11<2136::AID-CHEM2136>3.0.CO;2-G

[39]. Spackman, M. A.; Jayatilaka, D. Cryst. Eng. Comm. 2009, 11, 249-253.
https://doi.org/10.1039/B818330A

[40]. Hirshfeld, F. L. Theor. Chim. Acta. 1977, 44, 129-138.
https://doi.org/10.1007/BF00549096

[41]. Spackman, M. A.; Byrom P. G. Chem. Phys. Lett. 1997, 267, 215-220.
https://doi.org/10.1016/S0009-2614(97)00100-0

[42]. Rohl, A. L.; Moret, M.; Kaminsky, W.; Claborn, K.; McKinnon, J. J.; Kahr, B. Cryst. Growth Des. 2008, 8, 4517-4525.
https://doi.org/10.1021/cg8005212

[43]. Wolff S. K.; Grimwood D. J.; McKinnon J. J.; Turner M. J.; Jayatilaka D.; Spackman M. A. Crystal Explorer, the University of Western Australia, Australia, 2012.

[44]. Skovsen, I.; Christensen, M.; Clausen, H. F.; Overgaard, J.; Stiewe, C.; De gupta, T.; Mueller, E.; Spackman, M. A.; Iversen, B. B. Inorg. Chem. 2010, 49, 9343-9349.
https://doi.org/10.1021/ic100990a

[45]. Xavier, R. J.; Dinesh, P. Spectrochim. Acta A 2014, 118, 999-1011.
https://doi.org/10.1016/j.saa.2013.09.120

[46]. Scrocco, E.; Tomasi, J. Adv. Quant. Chem. 1978, 103, 115-193.
https://doi.org/10.1016/S0065-3276(08)60236-1

[47]. Luque, F. J.; Lopez, J. M.; Orozco, M. Theor. Chem. Acc. 2000, 103, 343-345.
https://doi.org/10.1007/s002149900013

[48]. Politzer, P.; Murray, J. S.; in: D. L. Beveridge; R. Lavery (Eds.), Theoretical Biochemistry and Molecular Biophysics: A Comprehensive Survey, Protein, Adenine Press, Schenectady, New York, 2, 1991.

[49]. Scrocco, E.; Tomasi, J. Curr. Chem. 1973, 7, 95-170.

[50]. Prachumrak, N.; Pansay, S.; Namuangruk, S.; Kaewin, T.; Jungsuttiwong S.; Sudyoadsuk; T.; Promarak V. Eur. J. Org. Chem. 2013, 29, 6619-6623.
https://doi.org/10.1002/ejoc.201300757

[51]. Kotchapadist, P.; Prachumrak, N.; Sunonnam, T.; Namuangruk, S.; Sudyoadsuk, T.; Keawin, T.; Jungsuttiwong, S.; Promarak, V. Eur. J. Org. Chem. 2015, 3, 496-505.
https://doi.org/10.1002/ejoc.201402680

[52]. Deshapande, N.; Belavagi N. S.; Sunagar M. G.; Gaonkar S.; Pujar G. H.; Wari M. N.; Inamdar S. R.; Khazi I. A. M. RSC Adv. 2015, 5, 86685-86696.
https://doi.org/10.1039/C5RA14550C

[53]. Mulliken, R. S. J. Chem. Phys. 1955, 23, 1833-1840.
https://doi.org/10.1063/1.1740588

[54]. Kose, E.; Atac, A.; Bardak, F. J. Mol. Struct. 2018, 1163, 147-160.
https://doi.org/10.1016/j.molstruc.2018.02.099

[55]. Benzon, K. B.; Varghese, H. T.; Yohannan-Panicker, C.; Pradhan, K.; Bipransh, K. T.; Ashis, K. N.; Van-Alsenoy, C. Spectrochim. Acta A 2015, 146, 307-322.
https://doi.org/10.1016/j.saa.2015.03.063

[56]. Weinhold, F.; Eric, D. Glendening, NBO 6. 0 Program Manual, University of Wisconsin, Madison, Wisconsin 53706, 2013.

Most read articles by the same author(s)

Kakkabevinahalli Hadagalli Nagachandra, J. R. Mannekutla, Shivkumar Math Amarayya, Sanjeev Ramchandra Inamdar, Solvent effect on the spectral properties of dipolar laser dyes: Evaluation of ground and excited state dipole moments , European Journal of Chemistry: Vol. 3 No. 2 (2012): June 2012
Mallikarjun Kalagouda Patil, Mare Goudar Kotresh, Tarimakki Shankar Tilakraj, Sanjeev Ramchandra Inamdar, Solvatochromism and ZINDO-IEFPCM solvation study on NHS ester activated AF514 and AF532 dyes: Evaluation of the dipole moments , European Journal of Chemistry: Vol. 13 No. 1 (2022): March 2022
Shilpa Mallappa Somagond, 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: Vol. 12 No. 4 (2021): December 2021
Shivaraj Mantur, Mallikarjun Kalagouda Patil, Afra Quasar Abdul Rasheed Nadaf, Mahesh Sadashivappa Najare, Mohammed Yaseen, Aravind Raviraj Nesaragi, Sanjeev Ramchandra Inamdar, Imtiyaz Ahmed Khazi, Ravindra Ramappa Kamble, Orange to red emissive aldehyde substituted donor-π-acceptor phenothiazine derivatives: Optoelectronic, DFT and thermal studies , European Journal of Chemistry: Vol. 14 No. 1 (2023): March 2023

TrendMD

Dimensions - Altmetric - scite_ - PlumX

Downloads and views

Downloads

Download data is not yet available.

Metrics

Metrics Loading ...

License Terms

License Terms

by-nc

Copyright © 2024 by Authors. This work is published and licensed by Atlanta Publishing House LLC, Atlanta, GA, USA. The full terms of this license are available at https://www.eurjchem.com/index.php/eurjchem/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 (https://www.eurjchem.com/index.php/eurjchem/terms) are administered by Atlanta Publishing House LLC (European Journal of Chemistry).

Article Sidebar

Main Article Content

Abstract

Article Details

Most read articles by the same author(s)

Downloads

Metrics