European Journal of Chemistry 2018, 9(3), 213-221. doi:10.5155/eurjchem.9.3.213-221.1713

Application of Hammett equation to intramolecular hydrogen bond strength in para-substituted phenyl ring of trifluorobenzoylacetone and 1-aryl-1,3-diketone malonates


Vahidreza Darugar (1) orcid , Mohammad Vakili (2,*) orcid , Sayyed Faramarz Tayyari (3) orcid , Fadhil Suleiman Kamounah (4) orcid , Raheleh Afzali (5) orcid

(1) Department of Chemistry, Faculty of Science, Ferdowsi University of Mashhad, Mashhad 91775-1436, Iran
(2) Department of Chemistry, Faculty of Science, Ferdowsi University of Mashhad, Mashhad 91775-1436, Iran
(3) Department of Chemistry, Faculty of Science, Ferdowsi University of Mashhad, Mashhad 91775-1436, Iran
(4) Department of Chemistry, University of Copenhagen, Universitetsparken 5, DK-2100, Copenhagen, Denmark
(5) Department of Chemistry, Faculty of Science, Ferdowsi University of Mashhad, Mashhad 91775-1436, Iran
(*) Corresponding Author

Received: 13 Apr 2018, Accepted: 02 Jun 2018, Published: 30 Sep 2018

Abstract


The stability of two stable cis-enol forms in two categories of β-diketones, including para-substituted of trifluorobenzoylacetone (X-TFBA) and 1-aryl-1,3-diketone malonates (X-ADM, X: H, NO2, OCH3, CH3, OH, CF3, F, Cl, and NH2) has been obtained by different theoretical methods. According to our results, the energy difference between the mentioned stable chelated enol forms for the titled compounds is negligible. The theoretical equilibrium constants between the two stable cis-enol of the mentioned molecules are in excellent agreement with the reported experimental equilibrium constant. In addition, the effect of different substitutions on the intramolecular hydrogen bond strength has been evaluated. The correlation between Hammett para-substituent constants, σp. with the theoretical and experimental parameters related to the strength of hydrogen bond in p-X-TFBA and p-X-ADM molecules also investigated by means of density functional theory calculations. The electronic effects of para-substitutions on the intramolecular hydrogen bond strength were determined by NMR and IR data related to intramolecular hydrogen bond strength, geometry, natural bond orbital results, and topological parameters. These parameters were correlated with the Hammett para-substituent constants, σp. Good linear correlations between σp and the several parameters related to the hydrogen bond strength, in this study were obtained.


Keywords


AIM; DFT; NBO; Hammett LFER; Substituent effect; Intramolecular hydrogen bond

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DOI: 10.5155/eurjchem.9.3.213-221.1713

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References

[1]. Huggins M.; Thesis, University of California, 1919.

[2]. Fuster, F.; Grabowski, S. J. J. Phys. Chem. A 2011, 115, 10078-10086.
https://doi.org/10.1021/jp2056859

[3]. Lopes Jesus, A. J.; Redinha, J. S. J. Phys. Chem. A 2011, 115, 14069-14077.
https://doi.org/10.1021/jp206193a

[4]. Zahedi-Tabrizi, M.; Farahati, R. Comp. Theor. Chem. 2011, 977, 195-200.
https://doi.org/10.1016/j.comptc.2011.09.034

[5]. Bende, A. Theor. Chem. Acc. 2010, 125, 253-268.
https://doi.org/10.1007/s00214-009-0645-6

[6]. Vakili, M.; Tayyari, S. F.; Kanaani, A.; Nekoei, A. R.; Salemi, S.; Miremad, H.; Berenji, A. R.; Sammelson, R. E. J. Mol. Struct. 2011, 998, 99-109.
https://doi.org/10.1016/j.molstruc.2011.04.045

[7]. Vakili, M.; Nekoei, A. R.; Tayyari, S. F.; Kanaani, A.; Sanati, N. J. Mol. Struct. 2012, 1021, 102-111.
https://doi.org/10.1016/j.molstruc.2012.04.009

[8]. Berenji, A. R.; Tayyari, S. F.; Rahimizadeh, M.; Eshghi, H.; Vakili, M.; Shiri, A. Spectrochim. Acta A 2013, 102, 350-357.
https://doi.org/10.1016/j.saa.2012.10.042

[9]. Gilli, G.; Gilli, P. The nature of hydrogen bond, Oxford: Oxford University Press, 2009.
https://doi.org/10.1093/acprof:oso/9780199558964.001.0001

[10]. Gilli, G.; Belluci, F.; Ferreti, V.; Bertolasi, V. J. Am. Chem. Soc. 1989, 111, 1023-1028.
https://doi.org/10.1021/ja00185a035

[11]. Bertolasi, V.; Gilli, P.; Ferreti, V.; Gilli, G. J. Am. Chem. Soc. 1991, 113, 4917-4925.
https://doi.org/10.1021/ja00013a030

[12]. Gilli, P.; Bertolasi, V.; Ferreti, V.; Gilli, G. J. Am. Chem. Soc. 1994, 116, 909-915.
https://doi.org/10.1021/ja00082a011

[13]. Tayyari, S. F.; Najafi, A.; Emamian, S.; Afzali, R.; Wang, Y. A. J. Mol. Struct. 2008, 878, 10-21.
https://doi.org/10.1016/j.molstruc.2007.07.040

[14]. Zahedi-Tabrizi, M.; Tayyari, F.; Moosavi-Tekyeh, Z.; Jalali, A.; Tayyari, S. F. Spectrochim. Acta A 2006, 65, 387-396.
https://doi.org/10.1016/j.saa.2005.11.019

[15]. Tayyari, S. F.; Milani-Nejad, F.; Rahemi, H. Spectrochim. Acta A 2002, 58, 1669-1679.
https://doi.org/10.1016/S1386-1425(01)00619-9

[16]. Darugar, V. R.; Vakili, M.; Nekoei, A. R.; Tayyari, S. F.; Afzali. R. J. Mol. Struct. 2017, 1150, 427-437.
https://doi.org/10.1016/j.molstruc.2017.09.004

[17]. Schwarzenbach, R. P.; Gschwend, P. M.; Imboden, D. M. Environmental Organic Chemistry, 2nd Ed.; Wiley-Interscience Publishers, 2003, 8, 253-268.

[18]. Jaffe, H. H. Chem. Rev. 1953, 53(2), 191-261.
https://doi.org/10.1021/cr60165a003

[19]. Yingst, A.; Mcdaniel, D. H. J. Inorg. Nucl. Chem. 1966, 28, 2919-2929.
https://doi.org/10.1016/0022-1902(66)80018-0

[20]. May, W. R.; Jones, M. M. J. Inorg. Nucl. Chem. 1962, 24, 511-517.
https://doi.org/10.1016/0022-1902(62)80237-1

[21]. Jimenez-Cruz, F. J.; Olivares, H. R.; Gutierrez, J. L.; Fragoza, M. L. J. Mol. Struc. 2015, 1101, 162-169.
https://doi.org/10.1016/j.molstruc.2015.08.022

[22]. Jimenez-Cruz, F. J.; Mar, L. F.; Gutierrez, J. L. J. Mol. Struc. 2013, 1034, 43-50.
https://doi.org/10.1016/j.molstruc.2012.09.010

[23]. Darugar, V. R.; Vakili, M.; Tayyari, S. F.; Eshghi, H.; Afzali, R. Orient. J. Chem. 2017, 5, 2579-2590.
https://doi.org/10.13005/ojc/330555

[24]. Bader, R. W. F.; Atoms in Molecules, A Quantum Theory, Oxford University Press, New York, 1990.

[25]. Emamian, S. R.; Tayyari, S. F. J. Chem. Sci. 2013, 125, 939-948.
https://doi.org/10.1007/s12039-013-0466-y

[26]. 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.; A. J. 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 A. 02, Wallingford CT, 2009.

[27]. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.
https://doi.org/10.1063/1.464913

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

[29]. Muller, C.; Plesset, M. S. Phys. Rev. 1934, 46, 618-622.
https://doi.org/10.1103/PhysRev.46.618

[30]. Frisch, M. J.; Head-Gordon, M.; Pople, J. A. Chem. Phys. Lett. 1990, 166, 275-280.
https://doi.org/10.1016/0009-2614(90)80029-D

[31]. Tao, J. M.; Perdew, J. P.; Staroverov, V. N.; Scuseria, G. E. Phys. Rev. Lett. 2003, 91, 146401-146404.
https://doi.org/10.1103/PhysRevLett.91.146401

[32]. Tomasi, J.; Persico, M. Chem. Rev. 1994, 94, 2027-2094.
https://doi.org/10.1021/cr00031a013

[33]. Biegler-König, F.; Schönbohm, J. J. Comput. Chem. 2002, 23, 1489-1494.
https://doi.org/10.1002/jcc.10085

[34]. Bader, R. F. W.; Tang, Y. H.; Tal, Y.; Biegler-König, F. W. J. Am. Chem. Soc. 1982, 104, 946-952.
https://doi.org/10.1021/ja00368a004

[35]. Glendening, E. D.; Badenhoop, J. K.; Reed, A. E.; Carpenter, J. E.; Bohmann, J. A.; Morales, C. M.; Weinhold, F. Theor. Chem. Inst.; University of Wisconsin, Madison, WI, 2001.

[36]. McWeeny, R. Phys. Rev. 1962, 126, 1028-1034.
https://doi.org/10.1103/PhysRev.126.1028

[37]. London, F. J. Phys. Radium 1937, 8, 397-409.
https://doi.org/10.1051/jphysrad:01937008010039700

[38]. Afzali, R.; Vakili, M.; Tayyari, S. F.; Eshghi, H.; Nekoei, A. R. Spectrochim. Acta A 2014, 117, 284-298.
https://doi.org/10.1016/j.saa.2013.08.032

[39]. Tayyari, S. F.; Vakili, M.; Nekoei, A. R.; Rahemi, H.; Wang, Y. A. Spectrochim. Acta A 2007, 66, 626-636.
https://doi.org/10.1016/j.saa.2006.04.002

[40]. Sloop, J. C.; Bumgardner, C. L.; Washington, G.; Loehle, W. D.; Sankar, S. S.; Lewis, A. B. J. Fluorine Chem. 2006, 127, 780-786.
https://doi.org/10.1016/j.jfluchem.2006.02.012

[41]. Lopes, A. J.; Redinha, J. S. J. Phys. Chem. A 2011, 115, 14069-14077.
https://doi.org/10.1021/jp110705c

[42]. Espinosa, E.; Molins, E.; Lecomte, C. Chem. Phys. Lett. 1998, 285, 170-173.
https://doi.org/10.1016/S0009-2614(98)00036-0

[43]. Afzali, R.; Vakili, M.; Nekoei, A. R.; Tayyari, S. F. J. Mol. Struct. 2014, 1076, 262-271.
https://doi.org/10.1016/j.molstruc.2014.07.059

[44]. Vakili, M.; Tayyari, S. F.; Nekoei, A. R.; Miremad, H.; Salemi, S.; Sammelson, R. E. J. Mol. Struct. 2010, 970, 160-170
https://doi.org/10.1016/j.molstruc.2010.02.072

[45]. Tayyari, S. F.; Emampour, J. S.; Vakili, M.; Nekoei, A. R.; Eshghi, H.; Salemi, S.; Hassanpour, M. J. Mol. Struct. 2006, 794, 204-214.
https://doi.org/10.1016/j.molstruc.2006.02.011

[46]. Cotman, A. E.; Cahard, D.; Mohar, B. Angew. Chem. 2016, 55, 5294-5298.
https://doi.org/10.1002/anie.201600812

[47]. Buttner, S.; Riahi, A.; Hussain, I.; Yawer, M. A.; Lubbe, M.; Villinger, A.; Reinke, H.; Fischer, C.; Langer, P. Tetrahedron 2009, 65, 2124-2135.
https://doi.org/10.1016/j.tet.2008.12.076

[48]. Reed, A. E.; Curtiss, L. A.; Weinhold, F. Chem. Rev. 1988, 88, 899-926.
https://doi.org/10.1021/cr00088a005

[49]. Wiberg, K. W. Tetrahedron 1968, 24, 1083-1096.
https://doi.org/10.1016/0040-4020(68)88057-3

[50]. Raj, R. K.; Gunasekaran, S.; Gnanasambandan, T.; Seshadri, S. Spectrochim. Acta A 2015, 139, 505-514.
https://doi.org/10.1016/j.saa.2014.12.024

[51]. Kosar, B.; Albayrak, C. Spectrochim. Acta A 2011, 87, 160-167.
https://doi.org/10.1016/j.saa.2010.09.016

[52]. Kanaani, A.; Ajloo, D.; Kiyani, H.; Ghasemian, H.; Vakili, M.; Feizabadi, M. Mol. Phys. 2016, 114, 2081-2097.
https://doi.org/10.1080/00268976.2016.1178822

[53]. Kanaani, A.; Ajloo, D.; Kiyani, H.; Ghasemian, H.; Vakili, M.; Mosallanezhad, A. Struct. Chem. 2015, 26, 1095-1113.
https://doi.org/10.1007/s11224-015-0571-2

[54]. Akman, F. Can. J. Phys. 2016, 94, 583-593.
https://doi.org/10.1139/cjp-2016-0041

[55]. Esmaeili, B.; Beyramabadi, S. A.; Sanavi-khoshnood, R.; Morsali, A. Orient. J. Chem. 2015, 31(4), 2129-2135.
https://doi.org/10.13005/ojc/310434


How to cite


Darugar, V.; Vakili, M.; Tayyari, S.; Kamounah, F.; Afzali, R. Eur. J. Chem. 2018, 9(3), 213-221. doi:10.5155/eurjchem.9.3.213-221.1713
Darugar, V.; Vakili, M.; Tayyari, S.; Kamounah, F.; Afzali, R. Application of Hammett equation to intramolecular hydrogen bond strength in para-substituted phenyl ring of trifluorobenzoylacetone and 1-aryl-1,3-diketone malonates. Eur. J. Chem. 2018, 9(3), 213-221. doi:10.5155/eurjchem.9.3.213-221.1713
Darugar, V., Vakili, M., Tayyari, S., Kamounah, F., & Afzali, R. (2018). Application of Hammett equation to intramolecular hydrogen bond strength in para-substituted phenyl ring of trifluorobenzoylacetone and 1-aryl-1,3-diketone malonates. European Journal of Chemistry, 9(3), 213-221. doi:10.5155/eurjchem.9.3.213-221.1713
Darugar, Vahidreza, Mohammad Vakili, Sayyed Faramarz Tayyari, Fadhil Suleiman Kamounah, & Raheleh Afzali. "Application of Hammett equation to intramolecular hydrogen bond strength in para-substituted phenyl ring of trifluorobenzoylacetone and 1-aryl-1,3-diketone malonates." European Journal of Chemistry [Online], 9.3 (2018): 213-221. Web. 17 Sep. 2019
Darugar, Vahidreza, Vakili, Mohammad, Tayyari, Sayyed, Kamounah, Fadhil, AND Afzali, Raheleh. "Application of Hammett equation to intramolecular hydrogen bond strength in para-substituted phenyl ring of trifluorobenzoylacetone and 1-aryl-1,3-diketone malonates" European Journal of Chemistry [Online], Volume 9 Number 3 (30 September 2018)

DOI Link: https://doi.org/10.5155/eurjchem.9.3.213-221.1713

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