European Journal of Chemistry 2023, 14(1), 90-98 | doi: https://doi.org/10.5155/eurjchem.14.1.90-98.2386 | 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

Synthesis, crystal structure, DFT/HF, Hirshfeld surface, and molecular docking analysis of 4-(tert-butyl)-4-nitro-1,1-biphenyl


Neha Kumari (1) orcid , Ruchika Sharma (2) orcid , Archana Akaram Yadav (3) orcid , Sandeep Ashok Sankpal (4) orcid , Jayakumar Mohan Raj (5) orcid , Saminathan Murugavel (6) orcid , Rajni Kant (7,*) orcid

(1) Department of Physics, University of Jammu, Jammu Tawi-180006, Jammu and Kashmir, India
(2) Department of Physics, University of Jammu, Jammu Tawi-180006, Jammu and Kashmir, India
(3) Department of Chemistry, Shivaji University Kolhapur-416004, Maharashtra, India
(4) Department of Chemistry, Shivaji University Kolhapur-416004, Maharashtra, India
(5) Department of Physics, Thanthai Periyar Government Institute of Technology, Vellore-632002, Tamil Nadu, India
(6) Department of Physics, Thanthai Periyar Government Institute of Technology, Vellore-632002, Tamil Nadu, India
(7) Department of Physics, University of Jammu, Jammu Tawi-180006, Jammu and Kashmir, India
(*) Corresponding Author

Received: 13 Dec 2022 | Revised: 10 Jan 2023 | Accepted: 12 Jan 2023 | Published: 31 Mar 2023 | Issue Date: March 2023

Abstract


4-(tert-Butyl)-4-nitro-1,1-biphenyl has been synthesized, and its structure has been characterized by using some spectroscopic and single-crystal X-ray diffraction techniques. It crystallizes in a monoclinic crystal system with space group P21/n and unit cell parameters: a = 6.4478(3) Å, b = 9.2477(4) Å, c = 23.4572(9) Å, β = 95.114(4)°, V = 1393.11(10) Å3, Z = 4. The molecular structure has been solved by using the intrinsic phasing method. The crystal structure is stabilized by C-H···O interactions. Computational studies were performed using density functional theory (DFT) and Hartree-Fock (HF) methods. The optimized geometry obtained from DFT and HF in the gas phase was compared with solid-phase experimental data retrieved from single-crystal X-ray diffraction results. Frontier molecular orbitals, such as the HOMO/LUMO energy gap, the molecular electrostatic potential, and Mulliken atomic charges, have been investigated. The HOMO LUMO energy gap of 3.97 eV indicates that the molecule is soft and highly reactive. The Hirshfeld surface analysis and their associated fingerprint plots have been used to quantitatively validate the interactions. Further insilico molecular docking studies have been performed with the molecular target Type-II topoisomerase (PDB ID: 1JIJ) and their results suggest that 4-(tert-butyl)-4-nitro-1,1-biphenyl could be considered an anticancer drug.


Announcements


One of our sponsors will cover the article processing fee for all submissions made between May 17, 2023 and June 16, 2023 (Voucher code: SPONSOR2023).

Editor-in-Chief
European Journal of Chemistry

Keywords


X-ray diffraction; Molecular docking; Hartree-Fock method; Single crystal structure; Density functional theory; Hirshfeld surface analysis

Full Text:

PDF
PDF    Open Access

DOI: 10.5155/eurjchem.14.1.90-98.2386

Links for Article


| | | | | | |

| | | | | | |

| | | |

Related Articles




Article Metrics

icon graph This Abstract was viewed 141 times | icon graph PDF Article downloaded 31 times

Funding information


University of Jammu for funding under the Rashtriya Uchchatar Shiksha Abhiyan (RUSA) 2.0 project of the Government of India.

References


[1]. Jain, Z. J.; Gide, P. S.; Kankate, R. S. Biphenyls and their derivatives as synthetically and pharmacologically important aromatic structural moieties. Arab. J. Chem. 2017, 10, S2051-S2066.
https://doi.org/10.1016/j.arabjc.2013.07.035

[2]. Bridges, J. W.; Creaven, P. J.; Williams, R. T. The fluorescence of some biphenyl derivatives. Biochem. J. 1965, 96, 872-878.
https://doi.org/10.1042/bj0960872

[3]. Yamamura, K.; Ono, S.; Tabushi, I. New liquid crystals having 4,4′-biphenanthryl core. Tetrahedron Lett. 1988, 29, 1797-1798.
https://doi.org/10.1016/S0040-4039(00)82046-8

[4]. Hohnholz, D.; Schweikart, K.-H.; Subramanian, L. R.; Wedel, A.; Wischert, W.; Hanack, M. Synthesis and studies on luminescent biphenyl compounds. Synth. Met. 2000, 110, 141-152.
https://doi.org/10.1016/S0379-6779(99)00291-X

[5]. Cincinelli, R.; Zwick, V.; Musso, L.; Zuco, V.; De Cesare, M.; Zunino, F.; Simoes-Pires, C.; Nurisso, A.; Giannini, G.; Cuendet, M.; Dallavalle, S. Biphenyl-4-yl-acrylohydroxamic acids: Identification of a novel indolyl-substituted HDAC inhibitor with antitumor activity. Eur. J. Med. Chem. 2016, 112, 99-105.
https://doi.org/10.1016/j.ejmech.2016.02.001

[6]. Lee, C.-Y.; Choi, H.; Park, E.-Y.; Nguyen, T.-T.-L.; Maeng, H.-J.; Mee Lee, K.; Jun, H.-S.; Shin, D. Synthesis and anti-diabetic activity of novel biphenylsulfonamides as glucagon receptor antagonists. Chem. Biol. Drug Des. 2021, 98, 733-750.
https://doi.org/10.1111/cbdd.13928

[7]. Pisano, M.; Dettori, M. A.; Fabbri, D.; Delogu, G.; Palmieri, G.; Rozzo, C. Anticancer activity of two novel hydroxylated biphenyl compounds toward malignant melanoma cells. Int. J. Mol. Sci. 2021, 22, 5636.
https://doi.org/10.3390/ijms22115636

[8]. Zhao, D.; Zhao, S.; Zhao, L.; Zhang, X.; Wei, P.; Liu, C.; Hao, C.; Sun, B.; Su, X.; Cheng, M. Discovery of biphenyl imidazole derivatives as potent antifungal agents: Design, synthesis, and structure-activity relationship studies. Bioorg. Med. Chem. 2017, 25, 750-758.
https://doi.org/10.1016/j.bmc.2016.11.051

[9]. Deep, A.; Jain, S.; Sharma, P. C. Synthesis and anti-inflammatory activity of some novel biphenyl-4-carboxylic acid 5-(arylidene)-2-(aryl)-4-oxothiazolidin-3-yl amides. Acta Pol. Pharm. 2010, 67, 63-67.

[10]. Morawska, K.; Jedlińska, K.; Smarzewska, S.; Metelka, R.; Ciesielski, W.; Guziejewski, D. Analysis and DNA interaction of the profluralin herbicide. Environ. Chem. Lett. 2019, 17, 1359-1365.
https://doi.org/10.1007/s10311-019-00865-1

[11]. Ghatge, S.; Yang, Y.; Moon, S.; Song, W.-Y.; Kim, T.-Y.; Liu, K.-H.; Hur, H.-G. A novel pathway for initial biotransformation of dinitroaniline herbicide butralin from a newly isolated bacterium Sphingopyxis sp. strain HMH. J. Hazard. Mater. 2021, 402, 123510.
https://doi.org/10.1016/j.jhazmat.2020.123510

[12]. Tavera-Hernández, R.; Jiménez-Estrada, M.; Alvarado-Sansininea, J. J.; Nieto-Camacho, A.; López-Muñoz, H.; Sánchez-Sánchez, L.; Escobar, M. L. Synthesis of chrysin, quercetin and naringin nitroderivatives: Antiproliferative, anti-inflammatory and antioxidant activity. Lett. Drug Des. Discov. 2021, 18, 795-805.
https://doi.org/10.2174/1570180818666210122162313

[13]. Ribeiro, T. A.; Machado-Ferreira, E.; Guimarães, L. F.; Cavaleiro, J.; Britto, A. M. A.; Redua, N.; de Souza, L. M. P.; Pimentel, A. S.; Picciani, P. H. S.; Oliveira, O. N., Jr; Barreto, C. B.; Soares, C. A. G. Novel cytotoxic amphiphilic nitro-compounds derived from a synthetic route for paraconic acids. Colloids Surf. A Physicochem. Eng. Asp. 2021, 626, 126984.
https://doi.org/10.1016/j.colsurfa.2021.126984

[14]. Adedapo, A. D. A.; Ajayi, A. M.; Ekwunife, N. L.; Falayi, O. O.; Oyagbemi, A.; Omobowale, T. O.; Adedapo, A. A. Antihypertensive effect of Phragmanthera incana (Schum) Balle on NG-nitro-L-Arginine methyl ester (L-NAME) induced hypertensive rats. J. Ethnopharmacol. 2020, 257, 112888.
https://doi.org/10.1016/j.jep.2020.112888

[15]. Rice, A. M.; Long, Y.; King, S. B. Nitroaromatic antibiotics as nitrogen oxide sources. Biomolecules 2021, 11, 267.
https://doi.org/10.3390/biom11020267

[16]. Becker, F. F.; Mukhopadhyay, C.; Hackfeld, L.; Banik, I.; Banik, B. K. Polycyclic aromatic compounds as anticancer agents: synthesis and biological evaluation of dibenzofluorene derivatives. Bioorg. Med. Chem. 2000, 8, 2693-2699.
https://doi.org/10.1016/S0968-0896(00)00213-3

[17]. Bisel, P.; Al-Momani, L.; Müller, M. The tert-butyl group in chemistry and biology. Org. Biomol. Chem. 2008, 6, 2655-2665.
https://doi.org/10.1039/b800083b

[18]. Chkirate, K.; Akachar, J.; Hni, B.; Hökelek, T.; Anouar, E. H.; Talbaoui, A.; Mague, J. T.; Sebbar, N. K.; Ibrahimi, A.; Essassi, E. M. Synthesis, spectroscopic characterization, crystal structure, DFT, ESI-MS studies, molecular docking and in vitro antibacterial activity of 1,5-benzodiazepin-2-one derivatives. J. Mol. Struct. 2022, 1247, 131188.
https://doi.org/10.1016/j.molstruc.2021.131188

[19]. Carvalho, A. J. P.; Dordio, A. V.; Ramalho, J. P. P. A DFT study on the adsorption of benzodiazepines to vermiculite surfaces. J. Mol. Model. 2014, 20, 2336.
https://doi.org/10.1007/s00894-014-2336-z

[20]. Hok, L.; BoŽičević, L.; Sremec, H.; Šakić, D.; Vrček, V. Racemization of oxazepam and chiral 1,4-benzodiazepines. DFT study of the reaction mechanism in aqueous solution. Org. Biomol. Chem. 2019, 17, 1471-1479.
https://doi.org/10.1039/C8OB02991A

[21]. Ganjali Koli, M.; Azizi, K. Investigation of benzodiazepines (BZDs) in a DPPC lipid bilayer: Insights from molecular dynamics simulation and DFT calculations. J. Mol. Graph. Model. 2019, 90, 171-179.
https://doi.org/10.1016/j.jmgm.2019.04.012

[22]. McClendon, A. K.; Osheroff, N. DNA topoisomerase II, genotoxicity, and cancer. Mutat. Res. 2007, 623, 83-97.
https://doi.org/10.1016/j.mrfmmm.2007.06.009

[23]. Gibson, E. G.; Bax, B.; Chan, P. F.; Osheroff, N. Mechanistic and structural basis for the actions of the antibacterial gepotidacin against Staphylococcus aureus gyrase. ACS Infect. Dis. 2019, 5, 570-581.
https://doi.org/10.1021/acsinfecdis.8b00315

[24]. Sheldrick, G. M. A short history of SHELX. Acta Crystallogr. A 2008, 64, 112-122.
https://doi.org/10.1107/S0108767307043930

[25]. Sheldrick, G. M. SHELXT - integrated space-group and crystal-structure determination. Acta Crystallogr. A Found. Adv. 2015, 71, 3-8.
https://doi.org/10.1107/S2053273314026370

[26]. Dolomanov, O. V.; Bourhis, L. J.; Gildea, R. J.; Howard, J. A. K.; Puschmann, H. OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Crystallogr. 2009, 42, 339-341.
https://doi.org/10.1107/S0021889808042726

[27]. Spek, A. L. Structure validation in chemical crystallography. Acta Crystallogr. D Biol. Crystallogr. 2009, 65, 148-155.
https://doi.org/10.1107/S090744490804362X

[28]. Nardelli, M. Parst: A system of fortran routines for calculating molecular structure parameters from results of crystal structure analyses. Comput. Chem. 1983, 7, 95-98.
https://doi.org/10.1016/0097-8485(83)85001-3

[29]. 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. Mercury CSD 2.0- new features for the visualization and investigation of crystal structures. J. Appl. Crystallogr. 2008, 41, 466-470.
https://doi.org/10.1107/S0021889807067908

[30]. Lee, C.; Yang, W.; Parr, R. G. Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Phys. Rev. B Condens. Matter 1988, 37, 785-789.
https://doi.org/10.1103/PhysRevB.37.785

[31]. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 09, rev. A.01, Gaussian Inc. , Wallingford CT, 2013.

[32]. Dennington, R.; Keith, T. A.; Millam, J. M. GaussView, Version 6, Semichem Inc.; Shawnee Mission, KS, 2016.

[33]. Spackman, P. R.; Turner, M. J.; McKinnon, J. J.; Wolff, S. K.; Grimwood, D. J.; Jayatilaka, D.; Spackman, M. A. CrystalExplorer: a program for Hirshfeld surface analysis, visualization and quantitative analysis of molecular crystals. J. Appl. Crystallogr. 2021, 54, 1006-1011.
https://doi.org/10.1107/S1600576721002910

[34]. Morris, G. M.; Huey, R.; Lindstrom, W.; Sanner, M. F.; Belew, R. K.; Goodsell, D. S.; Olson, A. J. AutoDock4 and AutoDockTools4: Automated docking with selective receptor flexibility. J. Comput. Chem. 2009, 30, 2785-2791.
https://doi.org/10.1002/jcc.21256

[35]. Pai, E. F.; Krengel, U.; Petsko, G. A.; Goody, R. S.; Kabsch, W.; Wittinghofer, A. Refined crystal structure of the triphosphate conformation of H-ras p21 at 1.35 A resolution: implications for the mechanism of GTP hydrolysis. EMBO J. 1990, 9, 2351-2359.
https://doi.org/10.1002/j.1460-2075.1990.tb07409.x

[36]. Dassault Systѐmes BIOVIA, BIOVIA Workbook, Release 2021; BIOVIA DS Visualizer, Release 2021, San Diego: Dassault Systѐmes, 2021. https://discover.3ds.com/discovery-studio-visualizer-download (accessed 2022 -05 -14).

[37]. Rajnikant; Gupta, V. K.; Kumar, A.; Bamezai, R. K.; Sharma, N. K. Crystallography of 4,4 - bis-(n-propylamino) - biphenyl [C18N2H24]. Mol. Cryst. Liq. Cryst. 1999, 333, 237-242.
https://doi.org/10.1080/10587259908026007

[38]. Rajnikant; Dinesh; Singh, D. X-ray structure determination and analysis of hydrogen interactions in 3, 3′-dimethoxybiphenyl. Bull. Mater. Sci. (India) 2004, 27, 31-34.
https://doi.org/10.1007/BF02708481

[39]. Dhankhar, J.; González-Fernández, E.; Dong, C.-C.; Mukhopadhyay, T. K.; Linden, A.; Čorić, I. Spatial anion control on palladium for mild C-H arylation of Arenes. J. Am. Chem. Soc. 2020, 142, 19040-19046.
https://doi.org/10.1021/jacs.0c09611

[40]. Sharif, M.; Zeeshan, M.; Reimann, S.; Villinger, A.; Langer, P. One-pot synthesis of fluorinated terphenyls by site-selective Suzuki-Miyaura reactions of 1,4-dibromo-2-fluorobenzene. Tetrahedron Lett. 2010, 51, 2810-2812.
https://doi.org/10.1016/j.tetlet.2010.03.067

[41]. Zazouli, S.; Lâallam, L.; Ketatni, E. M. Synthesis of novel benzohydrazide and benzoic acid derivatives: Crystal Structure, Hirshfeld surface analysis and DFT computational studies. J. Mol. Struct. 2021, 1239, 130465.
https://doi.org/10.1016/j.molstruc.2021.130465

[42]. Aihara, J.-I. Weighted HOMO-LUMO energy separation as an index of kinetic stability for fullerenes. Theor. Chem. Acc. 1999, 102, 134-138.
https://doi.org/10.1007/s002140050483

[43]. Sallam, H. H.; Mohammed, Y. H. E.; Al-Ostoot, F. H.; Sridhar, M. A.; Khanum, S. A. Synthesis, structure analysis, DFT calculations, Hirshfeld surface studies, and energy frameworks of 6-Chloro-3-[(4-chloro-3-methylphenoxy)methyl][1,2,4]triazolo[4,3-b]pyridazine. J. Mol. Struct. 2021, 1237, 130282.
https://doi.org/10.1016/j.molstruc.2021.130282

[44]. Manne, R.; Åberg, T. Koopmans' theorem for inner-shell ionization. Chem. Phys. Lett. 1970, 7, 282-284.
https://doi.org/10.1016/0009-2614(70)80309-8

[45]. Priya, M. K.; Revathi, B. K.; Renuka, V.; Sathya, S.; Asirvatham, P. S. Molecular structure, spectroscopic (FT-IR, FT-Raman, 13C and 1H NMR) analysis, HOMO-LUMO energies, Mulliken, MEP and thermal properties of new chalcone derivative by DFT calculation. Mater. Today 2019, 8, 37-46.
https://doi.org/10.1016/j.matpr.2019.02.078

[46]. 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.
https://doi.org/10.5155/eurjchem.10.4.281-294.1844

[47]. Moro, S.; Bacilieri, M.; Ferrari, C.; Spalluto, G. Autocorrelation of molecular electrostatic potential surface properties combined with partial least squares analysis as alternative attractive tool to generate ligand-based 3D-QSARs. Curr. Drug Discov. Technol. 2005, 2, 13-21.
https://doi.org/10.2174/1570163053175439

[48]. Mathammal, R.; Sangeetha, K.; Sangeetha, M.; Mekala, R.; Gadheeja, S. Molecular structure, vibrational, UV, NMR, HOMO-LUMO, MEP, NLO, NBO analysis of 3,5 di tert butyl 4 hydroxy benzoic acid. J. Mol. Struct. 2016, 1120, 1-14.
https://doi.org/10.1016/j.molstruc.2016.05.008

[49]. Spackman, M. A.; McKinnon, J. J. Fingerprinting intermolecular interactions in molecular crystals. CrystEngComm 2002, 4, 378-392.
https://doi.org/10.1039/B203191B

[50]. Singh, M.; Anthal, S.; Srijana, P. J.; Narayana, B.; Sarojini, B. K.; Likhitha, U.; Kamal; Kant, R. Novel supramolecular co-crystal of 3-aminobenzoic acid with 4-acetyl-pyridine: Synthesis, X-ray structure, DFT and Hirshfeld surface analysis. J. Mol. Struct. 2022, 1262, 133061.
https://doi.org/10.1016/j.molstruc.2022.133061


Supporting information


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

How to cite


Kumari, N.; Sharma, R.; Yadav, A.; Sankpal, S.; Raj, J.; Murugavel, S.; Kant, R. Eur. J. Chem. 2023, 14(1), 90-98. doi:10.5155/eurjchem.14.1.90-98.2386
Kumari, N.; Sharma, R.; Yadav, A.; Sankpal, S.; Raj, J.; Murugavel, S.; Kant, R. Synthesis, crystal structure, DFT/HF, Hirshfeld surface, and molecular docking analysis of 4-(tert-butyl)-4-nitro-1,1-biphenyl. Eur. J. Chem. 2023, 14(1), 90-98. doi:10.5155/eurjchem.14.1.90-98.2386
Kumari, N., Sharma, R., Yadav, A., Sankpal, S., Raj, J., Murugavel, S., & Kant, R. (2023). Synthesis, crystal structure, DFT/HF, Hirshfeld surface, and molecular docking analysis of 4-(tert-butyl)-4-nitro-1,1-biphenyl. European Journal of Chemistry, 14(1), 90-98. doi:10.5155/eurjchem.14.1.90-98.2386
Kumari, Neha, Ruchika Sharma, Archana Akaram Yadav, Sandeep Ashok Sankpal, Jayakumar Mohan Raj, Saminathan Murugavel, & Rajni Kant. "Synthesis, crystal structure, DFT/HF, Hirshfeld surface, and molecular docking analysis of 4-(tert-butyl)-4-nitro-1,1-biphenyl." European Journal of Chemistry [Online], 14.1 (2023): 90-98. Web. 31 May. 2023
Kumari, Neha, Sharma, Ruchika, Yadav, Archana, Sankpal, Sandeep, Raj, Jayakumar, Murugavel, Saminathan, AND Kant, Rajni. "Synthesis, crystal structure, DFT/HF, Hirshfeld surface, and molecular docking analysis of 4-(tert-butyl)-4-nitro-1,1-biphenyl" European Journal of Chemistry [Online], Volume 14 Number 1 (31 March 2023)

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.14.1.90-98.2386


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 2023, 14(1), 90-98 | doi: https://doi.org/10.5155/eurjchem.14.1.90-98.2386 | Get rights and content

Refbacks

  • There are currently no refbacks.


Bookmark and Share


Copyright (c) 2023 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.