Email this article 
Hide
Show all
OPEN ACCESS | 
PEER-REVIEWED |
RESEARCH ARTICLE
|
DOWNLOAD PDF
|
VIEW FULL-TEXT PDF
| TOTAL VIEWS
Synthesis and detailed characterization of a newly synthesized chalcone, 3-(2,5-dimethoxyphenyl)-1-(naphthalen-2-yl)prop-2-en-1-one
Madhu Kumar Dogganal Jayappa (1)
, Prabhuswamy Akhileshwari (2,*) , Mandayam Anandalwar Sridhar (3) , Lohith Tumakuru Nagarajappa (4) , Shivegowda Nagaraju (5) , Subrayachar Raghavendra (6) , Manasa Dogganal Jayappa (7) (1) Faculty of Pharmacy, Ramaiah Institute of Applied Sciences, Bengaluru 560 054, India
(2) Department of Studies in Physics, Manasagangotri, University of Mysore, Mysuru 570 006, India
(3) Department of Studies in Physics, Manasagangotri, University of Mysore, Mysuru 570 006, India
(4) Department of Studies in Physics, Manasagangotri, University of Mysore, Mysuru 570 006, India
(5) Department of Engineering Physics, Adichunchanagiri Institute of Technology, Chikkamagaluru 577 102, India
(6) Department of Engineering Physics, Adichunchanagiri Institute of Technology, Chikkamagaluru 577 102, India
(7) Department of Applied Botany, Davanagere University, Davanagere 577 007, India
(*) Corresponding Author
Received: 12 Jan 2021 | Revised: 11 Feb 2021 | Accepted: 18 Feb 2021 | Published: 31 Mar 2021 | Issue Date: March 2021
Abstract
Chalcones are the main component of some natural compounds. The title compound, 3-(2,5-dimethoxyphenyl)-1-(naphthalen-2-yl)prop-2-en-1-one, was synthesized and characterized. The compound (C21H18O3) crystallizes in the triclinic system with the space group of P-1 (no. 2), a = 7.7705(4) Å, b = 10.2634(6) Å, c = 11.2487(6) Å, α = 79.655(5)°, β = 81.500(5)°, γ = 68.039(5)°, V = 815.28(9) Å3, Z = 2, T = 293(2) K, μ(MoKα) = 0.086 mm-1, Dcalc = 1.297 g/cm3, 9126 reflections measured (4.318° ≤ 2Θ ≤ 52.728°), 3302 unique (Rint = 0.0466, Rsigma = 0.0528) which were used in all calculations. The final R1 was 0.0568 (I > 2σ(I)) and wR2 was 0.1667 (all data). The crystal structure is stabilized by both short C-H···O inter- and intra-molecular interactions. In addition, the crystal structure is reinforced by π-π interactions. Hirshfeld surface analysis confirmed the presence of C-H···O intermolecular interactions. The two-dimensional fingerprint plots are used to visualize the individual interactions present in the molecule. DFT calculations were performed to know the energy levels of the frontier molecular orbitals (HOMO-LUMO). The energy gap between the frontier molecular orbitals shows the kinetic stability of the molecule. The chemical reactive sites are observed by generating MEP surface. Non-covalent interactions (NCIs) are analyzed using reduced density gradient (RDG) analysis.
Announcements
Our editors have decided to support scientists to publish their manuscripts in European Journal of Chemistry without any financial constraints.
1- The article processing fee will not be charged from the articles containing the single-crystal structure characterization or a DFT study between September 15, 2023 and October 31, 2023 (Voucher code: FALL2023).
2. A 50% discount will be applied to the article processing fee for submissions made between September 15, 2023 and October 31, 2023 by authors who have at least one publication in the European Journal of Chemistry (Voucher code: AUTHOR-3-2023).
3. Young writers will not be charged for the article processing fee between September 15, 2023 and October 31, 2023 (Voucher code: YOUNG2023).
Editor-in-Chief
European Journal of Chemistry
Keywords
Full Text:
PDF
DOI: 10.5155/eurjchem.12.1.69-76.2067
Links for Article
| | | | | | |
| | | | | | |
| | | |
Related Articles
Article Metrics
This Abstract was viewed 844 times |
PDF Article downloaded 364 times
Funding information
Department of Science and Technology - Karnataka Science and Technology Promotion Society (DST-KSTePS), Government of Karnataka, India.
Citations
[1]. P. Akhileshwari, K. R. Kiran, M. A. Sridhar, M. P. Sadashiva
Crystal Structure Characterization, Interaction Energy Analysis and DFT Studies of 3-(4-Chlorophenyl)-N-phenylquinoxalin-2-amine
Journal of Chemical Crystallography 53(2), 185, 2023
DOI: 10.1007/s10870-022-00959-9
[2]. Nesrin Mahmoud Morsy, Ashraf Sayed Hassan
Synthesis, reactions, and applications of chalcones: A review
European Journal of Chemistry 13(2), 241, 2022
DOI: 10.5155/eurjchem.13.2.241-252.2245
References
[1]. Rammohan, A.; Reddy, J. S.; Sravya, G.; Rao, C. N.; Zyryanov, G. V. Environ. Chem. Lett. 2020, 18 (2), 433-458.
https://doi.org/10.1007/s10311-019-00959-w
[2]. Budhiraja, A.; Kadian, K.; Kaur, M.; Aggarwal, V.; Garg, A.; Sapra, S.; Nepali, K.; Suri, O. P.; Dhar, K. L. Med. Chem. Res. 2011, 21 (9), 2133-2140.
https://doi.org/10.1007/s00044-011-9733-y
[3]. Nishimura, R.; Tabata, K.; Arakawa, M.; Ito, Y.; Kimura, Y.; Akihisa, T.; Nagai, H.; Sakuma, A.; Kohno, H.; Suzuki, T. Biol. Pharm. Bull. 2007, 30 (10), 1878-1883.
https://doi.org/10.1248/bpb.30.1878
[4]. Chen, J. J.; Cheng, M. J.; Shu, C. W.; Sung, P. J.; Lim, Y. P.; Cheng, L. Y.; Wang, S. L.; Chen, L. C. Chem. Nat. Compd. 2017, 53 (4), 632-634.
https://doi.org/10.1007/s10600-017-2077-1
[5]. Song-San, S.; Watanabe, S.; Saito, T. Phytochemistry 1989, 28 (6), 1776-1777.
https://doi.org/10.1016/S0031-9422(00)97849-X
[6]. Lei, W.; Sun, M.; Luo, K. M.; Shui, X. R.; Sun, Y. M.; Tang, S. H. Mol. Biol. 2009, 43 (6), 1008-1013.
https://doi.org/10.1134/S0026893309060144
[7]. Fang, X.; Yang, B.; Cheng, Z.; Zhang, P.; Yang, M. Res. Chem. Intermed. 2013, 40 (4), 1715-1725.
https://doi.org/10.1007/s11164-013-1076-5
[8]. Chavan, B. B.; Gadekar, A. S.; Mehta, P. P.; Vawhal, P. K.; Kolsure, A. K.; Chabukswar, A. R. Asian. J. Bio. Phar. Sci. 2016, 6 (56), 1-7.
[9]. Rahman, M. Chem. Sci. J. 2011, 2 (1), CSJ-29, 1-16.
https://doi.org/10.4172/2150-3494.1000021
[10]. Mobinikhaled, A.; Foroughifar, N.; Zendehdel, M. Synth. React. Inorg., Met. Org., Nano-Met. Chem. 2007, 37 (4), 225-228.
https://doi.org/10.1080/15533170701313483
[11]. Budhiraja, A.; Kadian, K.; Kaur, M.; Aggarwal, V.; Garg, A.; Sapra, S.; Nepali, K.; Suri, O. P.; Dhar, K. L. Med. Chem. Res. 2011, 21 (9), 2133-2140.
https://doi.org/10.1007/s00044-011-9733-y
[12]. Kalirajan, R.; Sivakumar, S. U.; Jubie, S.; Gowramma, B.; Suresh, B. Int. J. Chem. Tech. Res. 2009, 1 (1), 27-34.
[13]. Madhu, K. D. J.; Jagadeesh, P. D.; Prakash, A. C.; Sana, S.; Chandrashekar, K. R. Int. J. Adv. Res. Chem. Sci. 2015, 2 (7), 43-51.
[14]. Rigaku, CrystalClear-SM Expert and CrystalStructure. Rigaku Corporation, Tokyo, Japan, 2011.
[15]. Sheldrick, G. M. Acta Cryst. A 2007, 64 (1), 112-122.
https://doi.org/10.1107/S0108767307043930
[16]. Johnson, C. K. ORTEP-II: A FORTRAN Thermal-Ellipsoid Plot Program for Crystal Structure Illustrations; Office of Scientific and Technical Information (OSTI), Oak Ridge National Laboratory Report ORNL-5138, 1976.
https://doi.org/10.2172/7364501
[17]. Macrae, C. F.; Sovago, I.; Cottrell, S. J.; Galek, P. T. A.; McCabe, P.; Pidcock, E.; Platings, M.; Shields, G. P.; Stevens, J. S.; Towler, M.; Wood, P. A. J. Appl. Cryst. 2020, 53 (1), 226-235.
https://doi.org/10.1107/S1600576719014092
[18]. Allen, F. H.; Kennard, O.; Watson, D. G.; Brammer, L.; Orpen, A. G.; Taylor, R. J. Chem. Soc., Perkin Trans. 2 1987, 12, S1-19.
https://doi.org/10.1039/p298700000s1
[19]. Pramodh, B.; Lokanath, N. K.; Naveen, S.; Naresh, P.; Ganguly, S.; Panda, J. J. Mol. Struc. 2018, 1161, 9-17.
https://doi.org/10.1016/j.molstruc.2018.01.078
[20]. Spackman, M. A.; Byrom, P. G. Chem. Phys. Lett. 1997, 267 (3-4), 215-220.
https://doi.org/10.1016/S0009-2614(97)00100-0
[21]. Spackman, M. A.; Jayatilaka, D. CrystEngComm 2009, 11 (1), 19-32.
https://doi.org/10.1039/B818330A
[22]. Kumara, K.; Jyothi, M.; Zabiulla; Shivalingegowda, N.; Khanum, S. A.; Krishnappagowda, L. N. Chem. Data Collect. 2017, 9-10, 152-163.
https://doi.org/10.1016/j.cdc.2017.06.003
[23]. Jayatilaka, D.; Wolff, S. K.; Grimwood, D. J.; McKinnon, J. J.; Spackman, M. A. Acta Cryst. A 2006, 62 (a1), s90-s90.
https://doi.org/10.1107/S0108767306098199
[24]. Schmidt, M. W.; Baldridge, K. K.; Boatz, J. A.; Elbert, S. T.; Gordon, M. S.; Jensen, J. H.; Koseki, S.; Matsunaga, N.; Nguyen, K. A.; Su, S.; Windus, T. L.; Dupuis, M.; Montgomery, J. A. J. Comput. Chem. 1993, 14 (11), 1347-1363.
https://doi.org/10.1002/jcc.540141112
[25]. Karuppasamy, P.; Kamalesh, T.; Anitha, K.; Abdul Kalam, S.; Senthil Pandian, M.; Ramasamy, P.; Verma, S.; Venugopal Rao, S. Optical Mater. 2018, 84, 475-489.
https://doi.org/10.1016/j.optmat.2018.07.039
[26]. Pearson, R. G. J. Chem. Sci. 2005, 117 (5), 369-377.
https://doi.org/10.1007/BF02708340
[27]. Aihara, J. Theoret. Chim. Acta 1999, 102 (1-6), 134-138.
[28]. Scrocco, E.; Tomasi, J. Electronic Molecular Structure, Reactivity and Intermolecular Forces: An Euristic Interpretation by Means of Electrostatic Molecular Potentials. In Advances in Quantum Chemistry Volume 11; Elsevier, 1978; pp 115-193.
https://doi.org/10.1016/S0065-3276(08)60236-1
[29]. Lu, T.; Chen, F. J. Comput. Chem. 2011, 33 (5), 580-592.
https://doi.org/10.1002/jcc.22885
[30]. Laplaza, R.; Peccati, F.; A. Boto, R.; Quan, C.; Carbone, A.; Piquemal, J.; Maday, Y.; Contreras‐Garcia, J. WIREs Comput. Mol. Sci. 2020, e1497, 1-18.
[31]. Humphrey, W.; Dalke, A.; Schulten, K. J. Mol. Graph. 1996, 14 (1), 33-38.
https://doi.org/10.1016/0263-7855(96)00018-5
Supporting information
The Supplementary Material for this article can be found online at: Supplementary files
How to cite
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.12.1.69-76.2067
| 
| 
| 
| 
| 
| 
| 
| 
| 
| 
| 
| 
| 
| 
| 
Save to Zotero
Save to Mendeley
European Journal of Chemistry 2021, 12(1), 69-76 | doi: https://doi.org/10.5155/eurjchem.12.1.69-76.2067 | Get rights and content
Refbacks
- There are currently no refbacks.
Copyright (c) 2021 Authors
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.