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Vol. 32 No. 12 (2020): Vol 32 Issue 12, 2020

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Crystal Structure, Hirshfeld Surface and Frontier Molecular Orbital Analyses of N-[2-(trifluoromethyl)phenyl]succinamic Acid

https://doi.org/10.14233/ajchem.2020.22860
P.A. Suchetan
Department of Studies and Research in Chemistry, University College of Science, Tumkur University, Tumkur-572103, India
S. Naveen
Department of Physics, Faculty of Engineering & Technology, JAIN (Deemed-to-be University), Jain Global Campus, Ramanagara 562 112, India
N.K. Lokanath
Department of Studies in Physics, University of Mysore, Manasagangotri, Mysuru-570006, India
P. Krishna Murthy
Department of Chemistry, Bapatla Engineering College (Autonomous), Bapatla-522101, India
M.V. Deepa Urs
Department of Physics, The National Institute of Engineering, Mysuru-570008, India

Corresponding Author(s) : P.A. Suchetan

pasuchetan@gmail.com

Asian Journal of Chemistry, Vol. 32 No. 12 (2020): Vol 32 Issue 12, 2020

Abstract

The ortho-CF3 substituent and the N-H bond are in syn-conformation in N-[2-(trifluoromethyl)phenyl]succinamic acid. In amide and acid functionalities, the carbonyl groups are directed in opposite directions to each other and their related-CH2 groups. syn-Conformation is observed for the acid functionality, where the carbonyl C=O and hydroxyl O-H bonds are directed in the same direction. Three planar fragments comprise of the molecule: aromatic ring (A), core portion -Carm-N(H)-C(=O)-C(H2)-C(H2)(B) and -C(H2)-C(=O)-OH(C). The dihedral angle between a pair of fragments being 48.6(4)º (A and B), 81.6 (4)º (B and C) and 70.5 (5)º (A and C). N-H•••O hydrogen bonds bind the molecules forming C(4) chains in the crystal, and the neighbouring anti-parallel chains are bound by O-H•••O hydrogen bonds resulting in a chair shaped ribbon of one-dimensional nature. The Hirshfeld surface study was carried out, including fingerprint plots. Studies have shown that the interactions with O•••H/H•••O (27.4%), H•••H (27.3%) and H•••F/F•••H (20.2%) substantially added to the surface. Theoretically, the highest occupied molecular orbital (HOMO), lowest unoccupied molecular orbital (LUMO) and various global reactivity descriptors were also computed by the density functional theory (DFT/B3LYP) approach with a 6-311G(d, p) basis set in the ground state on the geometrically optimized structure in the gas phase.

Keywords

Succinamic acid X-Ray diffraction Crystal structure Hydrogen bonds DFT calculations Hirshfeld Surfaces
Suchetan, P., Naveen, S., Lokanath, N., Krishna Murthy, P., & Deepa Urs, M. (2020). Crystal Structure, Hirshfeld Surface and Frontier Molecular Orbital Analyses of N-[2-(trifluoromethyl)phenyl]succinamic Acid. Asian Journal of Chemistry, 32(12), 3179–3185. https://doi.org/10.14233/ajchem.2020.22860
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References
  1. D. Burdulene, A. Palaima, Z. Stumbryavichyute, Z. Talaikite and V. Shimkyavichiene, Pharm. Chem. J., 33, 125 (1999); https://doi.org/10.1007/BF02508446
  2. D. Burdulene, Z. Stumbryavichyute, Z. Talaikite, G.V. Vladyko, E.I. Boreko and L.V. Korobchenko, Pharm. Chem. J., 31, 471 (1997); https://doi.org/10.1007/BF02464305
  3. D. Burdulene, Z. Stumbryavichyute, Z. Talaikite, G.V. Vladyko, E.I. Boreko and L.V. Korobchenko, Pharm. Chem. J., 30, 680 (1996); https://doi.org/10.1007/BF02223742
  4. D. Burdulene, Z. Stumbryavichyute, Z. Talaikite, G.A. Penyazeva, S.L. Buldakova, S.E. Metkalova, E.I. Drozdova, M.M. Olenin, V.A. Luchin and A.D. Shiryaev, Pharm. Chem. J., 29, 262 (1995); https://doi.org/10.1007/BF02219550
  5. L. Kubicova, K. Waisser, J. Kunes, K. Kralova, Z. Odlerova, M. Slosarek, J. Janota and Z. Svoboda, Molecules, 5, 714 (2000); https://doi.org/10.3390/50500714
  6. F. Hadizadeh, A. Moradi, G. Naghibi, M. Vojdani, J. Behravan and M. Ramezani, Int. J. Biomed. Sci., 3, 60 (2007).
  7. S.K. Seth, J. Mol. Struct., 70, 1064 (2014); https://doi.org/10.1016/j.molstruc.2014.01.068
  8. M.A. Spackman and J.J. McKinnon, CrystEngComm, 4, 378 (2002); https://doi.org/10.1039/B203191B
  9. M.A. Spackman, J.J. McKinnon and D. Jayatilaka, CrystEngComm, 10, 377 (2008); https://doi.org/10.1039/B715227B
  10. A. Maiti, A. Svizhenko and M.P. Anantram, Phys. Rev. Lett., 88, 1268051 (2002); https://doi.org/10.1103/PhysRevLett.88.126805
  11. D. Zhou, D. Ma, Y. Wang, X. Liu and X. Bao, Chem. Phys. Lett., 373, 46 (2003); https://doi.org/10.1016/S0009-2614(03)00513-X
  12. J. Leconte, A. Markovits, M.K. Skalli, C. Minot and A. Belmajdoub, Surf. Sci., 497, 194 (2002); https://doi.org/10.1016/S0039-6028(01)01477-7
  13. J.G. Wang, C.J. Liu, Z. Fang, Y. Liu and Z. Han, J. Phys. Chem. B, 108, 1653 (2004); https://doi.org/10.1021/jp035779o
  14. M.E. Vaschetto, B.A. Retamal and A.P. Monkman, J. Mol. Struct. THEOCHEM, 468, 209 (1999); https://doi.org/10.1016/S0166-1280(98)00624-1
  15. T. Clark, J. Chandrasekhar, G.W. Spitznagel and P.V.R. Schleyer, J. Comput. Chem., 4, 294 (1983); https://doi.org/10.1002/jcc.540040303
  16. S. Gronert, Chem. Phys. Lett., 252, 415 (1996); https://doi.org/10.1016/0009-2614(96)00162-5
  17. D.A. Forsyth and A.B. Sebag, J. Am. Chem. Soc., 119, 9483 (1997); https://doi.org/10.1021/ja970112z
  18. S. Armakovic, S.J. Armakovic and S. Koziel, Carbon, 111, 371 (2017); https://doi.org/10.1016/j.carbon.2016.10.022
  19. S. Armakovic, S.J. Armakovic and B.F. Abramovic, J. Mol. Model., 22, 240 (2016); https://doi.org/10.1007/s00894-016-3101-2
  20. B.T. Gowda, S. Foro, B.S. Saraswathi and H. Fuess, Acta Crystallogr. E, 67, o249 (2011); https://doi.org/10.1107/S160053681005364X
  21. Bruker. APEX2, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA (2004).
  22. G.M. Sheldrick, Acta Crystallogr. A, 71, 3 (2015); https://doi.org/10.1107/S2053273314026370
  23. A.L. Spek, Acta Crystallogr. A, 46, C34 (1990); https://doi.org/10.1107/S0108767390099780
  24. L.J. Farrugia, J. Appl. Cryst., 45, 849 (2012); https://doi.org/10.1107/S0021889812029111
  25. C.F. Macrae, I.J. Bruno, J.A. Chisholm, P.R. Edgington, P. McCabe, E. Pidcock, L. Rodriguez-Monge, R. Taylor, J. van de Streek and P.A. Wood, J. Appl. Cryst., 41, 466 (2008); https://doi.org/10.1107/S0021889807067908
  26. S.K. Wolff, D.J. Grimwood, J.J. McKinnon, D. Jayatilaka and M.A. Spackman, Crystal Explorer 3.0, University of Western Australia, Perth, Australia (2001).
  27. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G.A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H.P. Hratchian, A.F. Izmaylov, J. Bloino, G. Zheng, J.L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J.A. Montgomery Jr., J.E. Peralta, F. Ogliaro, M. Bearpark, J.J. Heyd, E. Brothers, K.N. Kudin, V.N. Staroverov, T. Keith, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J.C. Burant, S.S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J.M. Millam, M. Klene, J.E. Knox, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, R.L. Martin, K. Morokuma, V.G. Zakrzewski, G.A. Voth, P. Salvador, J.J. Dannenberg, S. Dapprich, A.D. Daniels, O. Farkas, J.B. Foresman, J.V. Ortiz, J. Cioslowski and D.J. Fox, Gaussian, Inc., Wallingford CT (2010).
  28. C. Lee, W. Yang and R.G. Parr, Phys. Rev. B Condens. Matter, 37, 785 (1988); https://doi.org/10.1103/PhysRevB.37.785
  29. A.D. Becke, J. Chem. Phys., 98, 5648 (1993); https://doi.org/10.1063/1.464913
  30. B.T. Gowda, S. Foro, B.S. Saraswathi and H. Fuess, Acta Crystallogr. E, 66, o908 (2010); https://doi.org/10.1107/S1600536810010329
  31. B.T. Gowda, S. Foro, B.S. Saraswathi, H. Terao and H. Fuess, Acta Crystallogr. E, 65, o399 (2009); https://doi.org/10.1107/S1600536809002979
  32. M.S. Krawczyk and I. Majerz, Acta Crystallogr. E, 75, 766 (2019); https://doi.org/10.1107/S2052520619009065
  33. M.J. Turner, J.J. Mckinnon, S.K. Wolff, D.J. Grimwood and P.R. Spackman, D. Jayatilaka and M. A. Spackman, CrystalExplorer17, The University of Western Australia, Perth, Australia (2017).
  34. T.A. Koopmans, Physica, 1, 104 (1934); https://doi.org/10.1016/S0031-8914(34)90011-2
  35. R.J. Parr, L.V. Szentpaly and S. Liu, J. Am. Chem. Soc., 121, 1922 (1999); https://doi.org/10.1021/ja983494x
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