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Synthesis, crystal structure elucidation, Hirshfeld surface analysis, 3D energy frameworks and DFT studies of 2-(4-fluorophenoxy) acetic acid
Akhileshwari Prabhuswamy (1,*)
, Yasser Hussein Eissa Mohammed (2) , Fares Hezam Al-Ostoot (3) , Geetha Doddanahalli Venkatesh (4) , Sridhar Mandayam Anandalwar (5) , Shaukath Ara Khanum (6) , Lokanath Neratur Krishnappagowda (7) (1) Department of Studies in Physics, Manasagangotri, University of Mysore, Mysuru 570 006, India
(2) Department of Chemistry, Yuvaraja’s College, University of Mysore, Mysuru 570 006, India
(3) Department of Chemistry, Yuvaraja’s College, University of Mysore, Mysuru 570 006, India
(4) Department of Studies in Physics, Manasagangotri, University of Mysore, Mysuru 570 006, India
(5) Department of Studies in Physics, Manasagangotri, University of Mysore, Mysuru 570 006, India
(6) Department of Chemistry, Yuvaraja’s College, University of Mysore, Mysuru 570 006, India
(7) Department of Studies in Physics, Manasagangotri, University of Mysore, Mysuru 570 006, India
(*) Corresponding Author
Received: 30 Jan 2021 | Revised: 26 Jul 2021 | Accepted: 07 Aug 2021 | Published: 30 Sep 2021 | Issue Date: September 2021
Abstract
The compound 2-(4-fluorophenoxy) acetic acid was synthesized by refluxing, 4-fluoro-phenol as a starting material with ethyl chloroacetate in acetone as solvent. The compound crystallizes in the monoclinic crystal system with the space group P21/c. Crystal data for C8H7FO3, a = 13.3087(17) Å, b = 4.9912(6) Å, c = 11.6018(15) Å, β = 104.171(4)°, V = 747.21(16) Å3, Z = 4, T = 293(2) K, μ(CuKα) = 1.142 mm-1, Dcalc = 1.512 g/cm3, 8759 reflections measured (13.72° ≤ 2Θ ≤ 130.62°), 1246 unique (Rint = 0.0528) which were used in all calculations. The final R1 was 0.0458 (>2sigma(I)) and wR2 was 0.1313 (all data). The structure was stabilized by C-H···O and C-H···Cg interactions. The intermolecular interactions in the crystal were studied using Hirshfeld surface analysis. 3D energy frameworks were computed to visualize the packing modes. DFT calculations were performed. The FMOs were studied to estimate the kinetic stability and reactivity of the molecule. The MEP surface was generated to investigate the charge distribution and chemical reactive sites in the molecule.
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DOI: 10.5155/eurjchem.12.3.304-313.2099
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[1]. Soundararajan Eswari, Subbiah Thirumaran
Synthesis, crystal structure, Hirshfeld surface analysis, and DFT studies on (2,2’-bipyridine)chlorobis(N,N-bis(thiophen-2-ylmethyl)dithiocarbamato-S,S’)zinc(II) complex
European Journal of Chemistry 13(1), 91, 2022
DOI: 10.5155/eurjchem.13.1.91-98.2212
References
[1]. Geetha, D. V.; Al-Ostoot, F. H.; Mohammed, Y. H. E.; Sridhar, M. A.; Khanum, S. A.; Lokanath, N. K. J. Mol. Struct. 2019, 1178, 384-393.
https://doi.org/10.1016/j.molstruc.2018.10.016
[2]. Sharma, G.; Anthal, S.; Geetha, D. V.; Al-Ostoot, F. H.; Hussein Eissa Mohammed, Y.; Ara Khanum, S.; Sridhar, M. A.; Kant, R. Mol. Cryst. Liq. Cryst. 2018, 675 (1), 85-95.
https://doi.org/10.1080/15421406.2019.1624051
[3]. Mohammed, Y. H. E.; Malojirao, V. H.; Thirusangu, P.; Al-Ghorbani, M.; Prabhakar, B. T.; Khanum, S. A. Eur. J. Med. Chem. 2018, 143, 1826-1839.
https://doi.org/10.1016/j.ejmech.2017.10.082
[4]. Haupt, K.; Dzgoev, A.; Mosbach, K. Anal. Chem. 1998, 70 (3), 628-631.
https://doi.org/10.1021/ac9711549
[5]. Zhang, H.; Song, T.; Zong, F.; Chen, T.; Pan, C. Int. J. Mol. Sci. 2008, 9 (1), 98-106.
https://doi.org/10.3390/ijms9010098
[6]. Mokale, S. N.; Nevase, M. C.; Sakle, N. S.; Dube, P. N.; Shelke, V. R.; Bhavale, S. A.; Begum, A. Bioorg. Med. Chem. Lett. 2014, 24 (9), 2155-2158.
https://doi.org/10.1016/j.bmcl.2014.03.030
[7]. Begum, S.; Bharathi, K.; Prasad, K. Int. J. Pharm. Pharm. Sci. 2016, 8 (10), 66-71.
https://doi.org/10.22159/ijpps.2016v8i10.5005
[8]. Wang, X.; Zhao, T.; Yang, B.; Li, Z.; Cui, J.; Dai, Y.; Qiu, Q.; Qiang, H.; Huang, W.; Qian, H. Bioorg. Med. Chem. 2015, 23 (1), 132-140.
https://doi.org/10.1016/j.bmc.2014.11.016
[9]. Kumara, K.; Al-Ostoot, F. H.; Mohammed, Y. H. E.; Khanum, S. A.; Lokanath, N. K. Chem. Data Coll. 2019, 20 (100195), 100195.
https://doi.org/10.1016/j.cdc.2019.100195
[10]. Takeda, Y.; Kawagoe, K.; Yokomizo, A.; Yokomizo, Y.; Hosokami, T.; Ogihara, Y.; Honda, Y.; Yokohama, S. Chem. Pharm. Bull. (Tokyo) 1998, 46 (3), 434-444.
https://doi.org/10.1248/cpb.46.434
[11]. Dahiya, R.; Kaur, R. Aust. J. Basic App. Sci. 2007, 1 (4), 525-532. http://www.ajbasweb.com/old/ajbas/525-532.pdf (accessed Jul 31, 2021).
[12]. Shahar Yar, M.; Bakht, M. A.; Siddiqui, A. A.; Abdullah, M. M.; De Clercq, E. J. Enzyme Inhib. Med. Chem. 2009, 24 (3), 876-882.
https://doi.org/10.1080/14756360802447917
[13]. Chandrika, P. M.; Yakaiah, T.; Rao, A. R. R.; Narsaiah, B.; Reddy, N. C.; Sridhar, V.; Rao, J. V. Eur. J. Med. Chem. 2008, 43 (4), 846-852.
https://doi.org/10.1016/j.ejmech.2007.06.010
[14]. Rani, P.; Pal, D., Kumar; Hegde, R., Rama; Hashim, S., Riaz. Hem. Ind. 2015, 69 (4), 405-415.
https://doi.org/10.2298/HEMIND140330057R
[15]. Tipparaju, S. K.; Muench, S. P.; Mui, E. J.; Ruzheinikov, S. N.; Lu, J. Z.; Hutson, S. L.; Kirisits, M. J.; Prigge, S. T.; Roberts, C. W.; Henriquez, F. L.; Kozikowski, A. P.; Rice, D. W.; McLeod, R. L. J. Med. Chem. 2010, 53 (17), 6287-6300.
https://doi.org/10.1021/jm9017724
[16]. Sun, A.; Prussia, A.; Zhan, W.; Murray, E. E.; Doyle, J.; Cheng, L.-T.; Yoon, J.-J.; Radchenko, E. V.; Palyulin, V. A.; Compans, R. W.; Liotta, D. C.; Plemper, R. K.; Snyder, J. P. J. Med. Chem. 2006, 49 (17), 5080-5092.
https://doi.org/10.1021/jm0602559
[17]. Nikalje, A. P. G.; Deshpande, D.; Une, H. D. Euro. J. Exp. Bio. 2012, 2 (2), 343-353. https://www.imedpub.com/articles/facile-synthesis-and-iin-vivoi-hypoglycemic-activity-of-novel-2-4hiazolidinedione-derivatives.pdf (accessed Jul 31, 2021).
[18]. Al-Ostoot, F. H.; Geetha, D. V.; Mohammed, Y. H. E.; Akhileshwari, P.; Sridhar, M. A.; Khanum, S. A. J. Mol. Struct. 2020, 1202 (127244), 127244.
https://doi.org/10.1016/j.molstruc.2019.127244
[19]. Al-Ostoot, F. H.; Mohammed, Y. H. E.; Zabiulla, A. N. K.; Khanum, S. A. J. Appl. Pharm. Sci. 2019, 9 (7), 42-49.
[20]. Eissa Mohammed, Y. H.; Thirusangu, P.; Vigneshwaran, V.; Prabhakar, B. T.; Khanum, S. A. Biomed. Pharmacother. 2017, 95, 375-386.
https://doi.org/10.1016/j.biopha.2017.08.105
[21]. Northover, B. J.; Verghese, J. J. Pharm. Pharmacol. 1962, 14 (1), 615-616.
https://doi.org/10.1111/j.2042-7158.1962.tb11149.x
[22]. Harsanyi, S.; Zamborsky, R.; Krajciova, L.; Kokavec, M.; Danisovic, L. Medicina (Kaunas) 2020, 56 (4), 153.
https://doi.org/10.3390/medicina56040153
[23]. Yang, X.; Xu, P.; Gao, Q.; Tan, M. Synth. React. Inorg. Met.-Org. Nano-Met. Chem. 2002, 32 (1), 59-68.
[24]. Sun, Z.; Ding, B.; Wu, B.; You, Y.; Ding, X.; Hou, X. J. Phys. Chem. C Nanomater. Interfaces 2012, 116 (3), 2543-2547.
https://doi.org/10.1021/jp205871a
[25]. Thomas, M. G.; Lawson, C.; Allanson, N. M.; Leslie, B. W.; Bottomley, J. R.; McBride, A.; Olusanya, O. A. Bioorg. Med. Chem. Lett. 2003, 13 (3), 423-426.
https://doi.org/10.1016/S0960-894X(02)00957-5
[26]. Ramadan, E. M.; Abou-Taleb, K. A.; Galal, G. F.; Abdel-Hamid, N. S. Ann. Agric. Sci. 2017, 62 (2), 151-159.
https://doi.org/10.1016/j.aoas.2017.11.002
[27]. Al-Ostoot, F. H.; Stondus, J.; Anthal, S.; Venkatesh, G. D.; Mohammed, Y. H. E.; Sridhar, M. A.; Khanum, S. A.; Kant, R. Eur. J. Chem. 2019, 10 (3), 234-238.
https://doi.org/10.5155/eurjchem.10.3.234-238.1874
[28]. Khamees, H. A.; Mohammed, Y. H. E.; Ananda; Al-Ostoot, F. H.; Sangappa; Alghamdi, S.; Khanum, S. A.; Madegowda, M. J. Mol. Struct. 2020, 1199 (127024), 127024.
https://doi.org/10.1016/j.molstruc.2019.127024
[29]. Khamees, H. A.; Mohammed, Y. H. E.; Swamynayaka, A.; Al-Ostoot, F. H.; Sert, Y.; Alghamdi, S.; Khanum, S. A.; Madegowda, M. ChemistrySelect 2019, 4 (15), 4544-4558.
https://doi.org/10.1002/slct.201900646
[30]. Smith, G.; Lynch, D. E.; Sagatys, D. S.; Kennard, C. H. L.; Katekar, G. F. Aust. J. Chem. 1992, 45 (7), 1101-1108.
https://doi.org/10.1071/CH9921101
[31]. Mohammed, Y. H. I.; Naveen, S.; Mamatha, S. V.; Jyothi, M.; Khanum, S. A.; Lokanath, N. K. IUCrdata 2016, 1 (10), x161714. https://doi.org/10.1107/s2414314616017144.
https://doi.org/10.1107/S2414314616017144
[32]. Ahmad, N. A.; Naveen, S.; Karthik Kumara, K.; Jamalis, J.; Lokanath, N. K. Der Pharma Chem. 2016, 8 (2), 49-53.
[33]. Rigaku, CrystalClear, Rigaku Corporation, Tokyo, Japan, 2011.
[34]. Sheldrick, G. M. Acta Crystallogr. A 2008, 64 (Pt 1), 112-122.
https://doi.org/10.1107/S0108767307043930
[35]. Spek, A. L. Acta Crystallogr. D Biol. Crystallogr. 2009, 65 (Pt 2), 148-155.
https://doi.org/10.1107/S090744490804362X
[36]. 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. Crystallogr. 2020, 53 (Pt 1), 226-235.
https://doi.org/10.1107/S1600576719014092
[37]. McKinnon, J. J.; Spackman, M. A.; Mitchell, A. S. Acta Crystallogr. B 2004, 60 (Pt 6), 627-668.
https://doi.org/10.1107/S0108768104020300
[38]. Mackenzie, C. F.; Spackman, P. R.; Jayatilaka, D.; Spackman, M. A. IUCrJ 2017, 4 (Pt 5), 575-587.
https://doi.org/10.1107/S205225251700848X
[39]. Spackman, M. A.; Jayatilaka, D. CrystEngComm 2009, 11 (1), 19-32.
https://doi.org/10.1039/B818330A
[40]. McKinnon, J. J.; Jayatilaka, D.; Spackman, M. A. Chem. Commun. (Camb.) 2007, No. 37, 3814-3816.
https://doi.org/10.1039/b704980c
[41]. Turner, M. J.; Grabowsky, S.; Jayatilaka, D.; Spackman, M. A. J. Phys. Chem. Lett. 2014, 5 (24), 4249-4255.
https://doi.org/10.1021/jz502271c
[42]. Turner, M. J.; Thomas, S. P.; Shi, M. W.; Jayatilaka, D.; Spackman, M. A. Chem. Commun. (Camb.) 2015, 51 (18), 3735-3738.
https://doi.org/10.1039/C4CC09074H
[43]. 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
[44]. Akhileshwari, P.; Kiran, K. R.; Sridhar, M. A.; Sadashiva, M. P.; Lokanath, N. K. J. Mol. Struct. 2021, 1242 (130747), 130747.
https://doi.org/10.1016/j.molstruc.2021.130747
[45]. Bendjeddou, A.; Abbaz, T.; Ayari, A.; Benahmed, M.; Gouasmia, A.; Villemin, D. Orient. J. Chem. 2016, 32 (2), 799-806.
https://doi.org/10.13005/ojc/320205
[46]. Gasteiger, J.; Li, X.; Rudolph, C.; Sadowski, J.; Zupan, J. J. Am. Chem. Soc. 1994, 116 (11), 4608-4620.
https://doi.org/10.1021/ja00090a009
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DOI Link: https://doi.org/10.5155/eurjchem.12.3.304-313.2099
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