Skip to main content
SpringerLink
Log in

Intermolecular interactions in 2,4-dinitrophenylhydrazine hydrochloride hydrate: X-ray structural and quantum mechanical study

  • Research Article
  • Published:
Central European Journal of Chemistry

Abstract

2,4-dinitrophenylhydrazine hydrochloride hydrate (I) was determined by X-ray crystallography, and the intermolecular interaction energies were calculated in terms of Natural Bond Orbital analysis. The asymmetric unit of (I) consists of a dinitrophenylhydrazinium cation, a chloride anion and a water molecule. The interatomic distances and angles in (I) show no unusual values. In the structure there are intermolecular N—H⊎⊎⊎O, N—H⊎⊎⊎Cl, O—H⊎⊎⊎Cl, C—H⊎⊎⊎O hydrogen bonds with bonding energy ranging form 16.03 to 0.76 kcal mol−1. These hydrogen bonds create the following N1 motifs: 6D, S(5), S(6), C(6), C(9). N1D motifs become infinite at the third level and are 2C 23 (6), C 23 (7).

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. G.A. Jeffrey, W. Saenger, Hydrogen Bonding in Biological Structures (Springer-Verlag, Berlin, 1991)

    Google Scholar 

  2. G.A. Jeffrey, An Introduction to Hydrogen Bonding (Oxford University Press, New York, 1997)

    Google Scholar 

  3. L.M. Epstein, E.S. Shubina, Coord. Chem. Rev. 231, 165 (2002)

    Article  CAS  Google Scholar 

  4. D. Payer, A. Comisso, A. Dmitriev, T. Strunskus, N. Lin, C. Woll, A. DeVita, J.V. Barth, K. Kern, Chem. Europ. J. 13, 3900 (2007)

    Article  CAS  Google Scholar 

  5. T. Schnabel, A. Srivastava, J. Vrabec, H. Hasse, J. Phys. Chem. B 111, 9871 (2007)

    Article  CAS  Google Scholar 

  6. N. M. Tonge, E.C. MacMahon, I. Pugliesi, M.C. Cockett, J. Chem. Phys. 126, 154319 (2007)

    Article  Google Scholar 

  7. C.J. Fecko, J.D. Eaves, J.J. Loparo, A. Tokmakoff, P. L. Geissler, Science 301, 1698 (2003)

    Article  CAS  Google Scholar 

  8. S.J. Suresh, J. Chem. Phys. 126, 204705 (2007)

    Article  CAS  Google Scholar 

  9. S.Z. Fisher, S. Anderson, R. Henning, K. Moffat, P. Langan, P. Thiyagarajand, A.J. Schultzd, Acta Crystallogr. D 63, 1178 (2007)

    Article  CAS  Google Scholar 

  10. K.H. Harmon, E. Nikolla, J. Mol. Struc. 657, 117 (2003)

    Article  CAS  Google Scholar 

  11. V. Villar, L. Irusta, M.J. Fernandez-Berridi, J.J. Iruin, M. Iriarte, L. Gargallo, D. Radic, Thermochimica acta 402, 209 (2003)

    CAS  Google Scholar 

  12. Z. Lin, Coord. Chem. Rev. 251, 2280 (2007)

    Article  CAS  Google Scholar 

  13. G. Smith, U. D. Wermuth, P.C. Healy, J. White, Australian J. Chem. 60, 264 (2007)

    Article  CAS  Google Scholar 

  14. A. Gavezzotti, Acta Crystallogr. B 64, 401 (2008)

    Article  Google Scholar 

  15. B.G. Oliveira, F.S. Pereira, R.C.M.U. de Araujo, M.N. Ramos, Chem Phys. Lett. 427, 181 (2006)

    Article  CAS  Google Scholar 

  16. N. Okabe, T. Nakamura, H. Fukuda, Acta Crystallogr. C 49, 1678 (1993)

    Article  Google Scholar 

  17. T.J. Bartczak, R. Kruszynski, Z. Chilmonczyk, J. Cybulski, Acta Crystallogr. E 57, o341 (2001)

    Article  Google Scholar 

  18. X-RED. Version 1.18 (STOE & Cie GmbH, Darmstadt Germany, 1999)

  19. G.M. Sheldrick, Acta Crystallogr. A46, 467 (1990)

    CAS  Google Scholar 

  20. G. M. Sheldrick, SHELXL97 Program for the Solution and Refinement of Crystal Structures (University of Göttingen, Göttingen Germany, 1997)

    Google Scholar 

  21. G. M. Sheldrick, SHELXTL: release 4.1 for Siemens Crystallographic Research Systems (Siemens Analytical X-Ray Instruments Inc., Madison USA, 1990)

    Google Scholar 

  22. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, Jr., T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, 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, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, and J. A. Pople, Gaussian 03, Revision C.02 (Gaussian Inc., Wallingford CT USA, 2004)

    Google Scholar 

  23. J.P. Foster, F.A. Weinhold, J. Am. Chem. Soc. 102, 7211 (1980)

    Article  CAS  Google Scholar 

  24. A.E. Reed, F.A. Weinhold, J. Chem. Phys. 83, 1736 (1985)

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of X-Ray Crystallography and Crystal Chemistry, Institute of General and Ecological Chemistry, Technical University of Lodz, 90-924, Łódź, Poland

    Rafal Kruszynski

Authors
  1. Rafal Kruszynski
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Rafal Kruszynski.

About this article

Cite this article

Kruszynski, R. Intermolecular interactions in 2,4-dinitrophenylhydrazine hydrochloride hydrate: X-ray structural and quantum mechanical study. cent.eur.j.chem. 6, 542–548 (2008). https://doi.org/10.2478/s11532-008-0067-7

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.2478/s11532-008-0067-7

Keywords

Search

Navigation