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Zeitschrift für Naturforschung B

A Journal of Chemical Sciences

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π-Electron delocalization in 2-benzoyl-5-phenylpyrazolidin-3-one

Monika Olesiejuk
  • Department of Chemical Organic Technology and Petrochemistry, The Silesian University of Technology, Krzywoustego 4, 44-100 Gliwice, Poland
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
/ Agnieszka Kudelko
  • Department of Chemical Organic Technology and Petrochemistry, The Silesian University of Technology, Krzywoustego 4, 44-100 Gliwice, Poland
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
/ Katarzyna Gajda / Błażej Dziuk / Krzysztof Ejsmont
Published Online: 2018-07-09 | DOI: https://doi.org/10.1515/znb-2018-0072

Abstract

The crystal and molecular structures of 2-benzoyl-5-phenylpyrazolidin-3-one have been characterized by X-ray diffraction along with density functional theory studies. Cinnamic acid chloride was reacted with benzhydrazide, yielding 2-benzoyl-5-phenylpyrazolidin-3-one. This product was formed in the transformation comprising the nucleophilic addition of benzhydrazide to the styryl fragment of the α,β-unsaturated arrangement and subsequent cyclization. The molecule contains two benzene rings and one five-membered heterocyclic ring with an N–N single bond. The five-membered ring is composed of three atoms of sp3 hybridization and two atoms of sp2 hybridization, which cause the flattening of the heterocyclic ring. The Harmonic Oscillator Model of Aromaticity and Nucleus-Independent Chemical Shift indexes, calculated for the benzene rings, demonstrate that there are no substantial interactions between the regions of π-electron delocalization in the molecule. In the crystal structure, there are N–H···O hydrogen bonds that link the molecules along the crystallographic c axis and weak intermolecular C–H···O hydrogen bonds.

Graphical Abstract

Keywords: addition; benzhydrazide; crystal structure; X-ray structure determination

References

  • [1]

    Ş. G. Küçükgüzel, S. Rollas, H. Erdeniz, M. Kiraz, A. Cevdet Ekinci, A. Vidin, Eur. J. Med. Chem. 2000, 35, 761.CrossrefGoogle Scholar

  • [2]

    S. A. F. Rostom, I. M. El-Ashmawy, H. A. Abd El Razik, M. H. Badr, H. M. A. Ashour, Bioorg. Med. Chem. 2009, 17, 882.CrossrefGoogle Scholar

  • [3]

    S. Khode, V. Maddi, P. Aragade, M. Palkar, P. K. Ronad, S. Mamledesai, A. H. M. Thippeswamy, D. Satyanarayana, Eur. J. Med. Chem. 2009, 44, 1682.CrossrefGoogle Scholar

  • [4]

    M. Abdel-Aziz, G. E. A. Abuo-Rahma, A. A. Hassan, Eur. J. Med. Chem. 2009, 44, 3480.CrossrefGoogle Scholar

  • [5]

    Z. S. Quan, R. L. Li, Y. Z. Ling, Acta Pharm. Sin. B 1992, 27, 711.Google Scholar

  • [6]

    N. Das, A. Verma, P. K. Shrivastava, S. K. Shrivastava, Indian J. Chem. Sect. B 2008, 47, 1555.Google Scholar

  • [7]

    G. Ouyang, Z. Chen, X. Cai, B. A. Song, P. S. Bhadury, S. Yang, L. H. Jin, W. Xue, D. Y. Hu, S. Zeng, Bioorg. Med. Chem. 2008, 16, 9699.CrossrefGoogle Scholar

  • [8]

    D. Castagnolo, F. Manetti, M. Radi, B. Bechi, M. Pagano, A. De Logu, R. Meleddu, M. Saddi, M. Botta, Bioorg. Med. Chem. Lett. 2009, 17, 5716.CrossrefGoogle Scholar

  • [9]

    K. B. Umesha, K. M. L. Rai, M. A. Harish Nayaka, Int. J. Biomed. Sci. 2009, 5, 359.Google Scholar

  • [10]

    R. Tripathy, A. Ghose, J. Singh, E. R. Bacon, T. S. Angeles, S. X. Yang, M. S. Albom, L. D. Aimone, J. L. Herman, J. P. Mallamo, Bioorg. Med. Chem. Lett. 2007, 17, 1793.CrossrefGoogle Scholar

  • [11]

    H. Park, K. Lee, S. Park, B. Ahn, J. Lee, H. Cho, K. Lee, Bioorg. Med. Chem. Lett. 2005, 15, 3307.CrossrefGoogle Scholar

  • [12]

    H. Dorn, Chem. Heterocycl. Compd. 1981, 17, 1.CrossrefGoogle Scholar

  • [13]

    G. Varvounis, Y. Fiamegos, G. Pilidis, Adv. Heterocycl. Chem. 2001, 80, 75.Google Scholar

  • [14]

    T. Eicher, S. Hauptmann, The Chemistry of Heterocycles, 2nd edition, Wiley-VCH, Weinheim, 2003.Google Scholar

  • [15]

    R. M. Claramunt, J. Elguero, Org. Prep. Proced. Int. 1991, 23, 273.CrossrefGoogle Scholar

  • [16]

    U. Grošelj, J. Svete, ARKIVOC 2015, 6, 175.Google Scholar

  • [17]

    F. H. Allen, Acta Crystallogr. 2002, B58, 380.Google Scholar

  • [18]

    S. K. Mohamed, M. Akkurt, J. T. Mague, E. A. Ahmed, M. R. Albayati, Acta Crystallogr. 2014, E70, 938.Google Scholar

  • [19]

    O. Dideberg, L. Dupont, J. Toussaint, Acta Crystallogr. 1974, B30, 2444.Google Scholar

  • [20]

    G. Fritsch, G. Zinner, M. Beimel, D. Mootz, H. Wunderlich, Arch. Pharm. Chem. Life Sci. 1986, 319, 70.CrossrefGoogle Scholar

  • [21]

    R. A. Izydore, J. A. Bernal-Ramirez, P. Singh, J. Org. Chem. 1990, 55, 3761.CrossrefGoogle Scholar

  • [22]

    P. K. Mogensen, O. Simonsen, Acta Crystallogr. 1991, C47, 1854.Google Scholar

  • [23]

    X. Wang, W. Wang, Y. Wen, L. He, X. Zhu, Synthesis 2008, 20, 3223.Google Scholar

  • [24]

    Q. Yang, N. Ni, X. Xu, Y. Tang. Acta Crystallogr. 1994, C50, 648.Google Scholar

  • [25]

    E. Gould, T. Lebl, A. M. Z. Slawin, M. Reid, T. Davies, A. D. Smith, Org. Biomol. Chem. 2013, 11, 7877.CrossrefGoogle Scholar

  • [26]

    F. H. Allen, D. G. Watson, L. Brammer, A. G. Orpen, R. Taylor, in International Tables for Crystallography (Ed.: E. Prince), 3rd edition, Mathematical, Physical and Chemical Tables C, Springer Verlag, Berlin, 2004, p. 790.Google Scholar

  • [27]

    J. Kruszewski, T. M. Krygowski, Tetrahedron Lett. 1973, 14, 3839.CrossrefGoogle Scholar

  • [28]

    T. M. Krygowski, J. Chem. Inf. Comput. Sci. 1993, 33, 70.CrossrefGoogle Scholar

  • [29]

    T. M. Krygowski, M. Cyrański, Tetrahedron 1996, 52, 10255.CrossrefGoogle Scholar

  • [30]

    P. V. R. Schleyer, C. Maerker, A. Dransfeld, H. Jiao, N. J. R. van E. Hommes, J. Am. Chem. Soc. 1996, 118, 6317.CrossrefGoogle Scholar

  • [31]

    M. K. Cyrański, T. M. Krygowski, M. Wisiorowski, N. J. R. van E. Hommes, P. V. R. Schleyer, Angew. Chem. Int. Ed. 1998, 37, 177.CrossrefGoogle Scholar

  • [32]

    Z. Chen, C. S. Wannere, C. Corminboeuf, R. Puchta, P. V. R. Schleyer, Chem. Rev. 2005, 105, 3842.CrossrefGoogle Scholar

  • [33]

    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, 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, Ö. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski, D. J. Fox, Gaussian 09, Gaussian, Inc., Wallingford, CT (USA) 2009.Google Scholar

  • [34]

    E. D. Glendening, A. E. Reed, J. E. Carpenter, F. Weinhold, NBO (version 3.1). See also: F. Weinhold, J. E. Carpenter, The Natural Bond Orbital Lewis Structure Concept for Molecules, Radicals, and Radical Ions In The Structure of Small Molecules and Ions (Eds.: R. Naaman, Z. Vager), Springer, Boston, 1988, p. 227. DOI: .CrossrefGoogle Scholar

  • [35]

    CrysAlis CCD and CrysAlis Red, Oxford Diffraction Ltd., Abingdon, Oxford (UK) 2008.Google Scholar

  • [36]

    M. Sheldrick, Acta Crystallogr. 2008, A64, 112.Google Scholar

  • [37]

    S. Parsons, H. D. Flack, T. Wagner, Acta Crystallogr. 2013, B69, 249.Google Scholar

  • [38]

    M. Sheldrick, Acta Crystallogr. 2015, C71, 3.Google Scholar

  • [39]

    A. D. Becke, Phys. Rev. A 1988, 38, 3098.CrossrefGoogle Scholar

  • [40]

    A. D. Becke, J. Chem. Phys. 1993, 98, 5648.CrossrefGoogle Scholar

  • [41]

    C. Lee, W. Yang, R. G. Parr, Phys. Rev. B. 1988, 37, 785.CrossrefGoogle Scholar

About the article

Received: 2018-04-16

Accepted: 2018-06-05

Published Online: 2018-07-09


Citation Information: Zeitschrift für Naturforschung B, 20180072, ISSN (Online) 1865-7117, ISSN (Print) 0932-0776, DOI: https://doi.org/10.1515/znb-2018-0072.

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