Structural Chemistry

, Volume 9, Issue 6, pp 395–402 | Cite as

The Electron Distribution in the Nonlinear Optical Material 2-Amino-5-Nitropyridinium Dihydrogen Phosphate

  • Anna Puig-Molina
  • Angel Alvarez-Larena
  • Juan F. Piniella
  • Sean T. Howard
  • François Baert

Abstract

The topological analysis of the 2-amino-5-nitropyridinium dihydrogen phosphate, 2A5NPDP, and the experimental electron density distribution determined from X-ray diffraction data interpreted in terms of the Hansen & Coppens pseudoatom formalism [1] is presented. The bond critical point properties of the total experimental electron density agree fairly well with ab initio Hartree-Fock calculations for the isolated ions. The analysis of the hydrogen-bond critical points shows the crystal H-bond framework to involve four anions and one cation. All the H-bond critical points show small positive ∇2ρ(r) values, consistent with ionic closed-shell interactions between the participant atoms.

Electron density topological analysis 2-amino-5-nitropyridinium dihydrogen phosphate nonlinear optics dipole moment 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

REFERENCES

  1. 1.
    Hansen, N. K.; Coppens, P. Acta Cryst. 1978, A34, 909–921.Google Scholar
  2. 2.
    Zyss, J.; Chemla, D. S. Nonlinear Optical Properties of Organic Molecules and Crystals, vol. 1; Academic Press: New York, 1987.Google Scholar
  3. 3.
    Masse, R.; Zyss, J. J. Mol. Eng. 1991, 1(2), 141–152.Google Scholar
  4. 4.
    Pecaut, J.; Levy, J. P.; Masse, R. J. Mater. Chem. 1993, 3(10), 999–1003.Google Scholar
  5. 5.
    Watanabe, O.; Noritake, T.; Hirose, Y.; Okada, A.; Kurauchi, T. J. Mater. Chem. 1993, 3(10), 1053–1057.Google Scholar
  6. 6.
    Kotler, Z.; Hierle, H.; Josse, D.; Zyss, J. J. Opt. Soc. Am. B 1992, 9, 534–547.Google Scholar
  7. 7.
    Samuel, I. D. W.; Villacampa, B.; Josse, D.; Khodja, S.; Zyss, J. Appl. Phys. Lett. 1995, 66(16), 2019–2021.Google Scholar
  8. 8.
    Hamzaoui, F. Ph.D. thesis. Université des Sciences et Technologies de Lille, France, 1995.Google Scholar
  9. 9.
    Hansen, N. K.; Protas, J.; Marnier, G. Acta Cryst. 1995, B47, 660–672.Google Scholar
  10. 10.
    Radaev, S. F.; Maximov, B. A.; Simonov, V. I.; Andreev, B.; D'Yakov, V. A. Acta Cryst. 1992, B48, 154–160.Google Scholar
  11. 11.
    Howard, S. T.; Hursthouse, M. B.; Lehmann, C. W.; Mallinson, P. R.; Frampton, C. S. J.Chem. Phys. 1992, 97(8), 5616–5630.Google Scholar
  12. 12.
    Fkyerat, A.; Guelzim, A.; Baert, F.; Paulus, W.; Heger, G.; Zyss, J.; Perigaud, A. Acta Cryst. 1995, B51, 197–209.Google Scholar
  13. 13.
    Khriffi, S. Ph.D. thesis. Unversité des Sciences et Technologies de Lille, France, 1996.Google Scholar
  14. 14.
    Espinosa, E. Ph.D. thesis. Universitat de Barcelona, Spain, 1994.Google Scholar
  15. 15.
    Lehmann, M. S.; Larsen, F. K. Acta Cryst. 1974, A30, 580–584.Google Scholar
  16. 16.
    Blessing, R. H. Cryst. Rev. 1987, 1, 3–58.Google Scholar
  17. 17.
    Koritsanszky, T.; Howard, S. T.; Su, Z. W.; Mallinson, P. R.; Richter, T.; Hansen, N. K. XD—A Computer Program Package for Multipole Refinement and Analysis of Electron Densities from Diffraction Data. Release May 1995, Free University of Berlin, Germany, 1995.Google Scholar
  18. 18.
    Stewart, R. F.; Davidson, E. R.; Simpson, W. T. J. Chem. Phys. 1965, 42, 3175–3187.Google Scholar
  19. 19.
    Hirshfeld, F. L. Israel J. Chem., 1977, 16, 226–229.Google Scholar
  20. 20.
    Eisenstein, M. Acta Cryst. 1988, B44, 412–426.Google Scholar
  21. 21.
    Baert, F.; Schweiss, P.; Heger, G.; More, M. J. Mol. Struct. 1988, 178, 29–48.Google Scholar
  22. 22.
    Blessing, R. H. Acta Cryst. 1988, B44, 334–340.Google Scholar
  23. 23.
    Weber, H. P.; Craven, B. M.; McMullan, R. K. Acta Cryst. 1980, B36, 645–649.Google Scholar
  24. 24.
    McMullan, R. K.; Benci, P.; Craven, B. M. Acta Cryst. 1980, B36, 1424–1430.Google Scholar
  25. 25.
    Ichikawa, M. Acta Cryst. 1987, B43, 23–28.Google Scholar
  26. 26.
    Bruning, H. Ph.D. thesis, University of Twente, Twente, The Netherlands, 1992.Google Scholar
  27. 27.
    Klein, C. L. Struct. Chem. 1991, 2, 507–514.Google Scholar
  28. 28.
    Schmidt, M. W.; Baldriche, K. K.; Boatz, J. A.; Elbert, S. T.; Gordon, M. S.; Jensen, J. J.; Koseki, S.; Matsunaga, N.; Emguyen, K. A.; Su, S.; Windus, T. L.; Dupuis, N.; Montgomery, J. A. GAMESS. J. Compt. Chem. 1993, 14, 1347–1363.Google Scholar
  29. 29.
    Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, Y.; Ayala, P. Y.; Chen, W.; Wong, N. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Brinkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, A. GAUSSIAN94. Revision D.2. Gaussian Inc., Pittsburgh, PA, 1995.Google Scholar
  30. 30.
    Biegler-Konig, F. W.; Bader, R. F. W.; Tang, R. J. J. Comput. Chem. 1982, 3, 317–328.Google Scholar
  31. 31.
    Coppens, P.; Guru Row, T. N.; Leung, P.; Stevens, E. D.; Becker, P. J.; Yang, Y. W. Acta Cryst. 1979, A35, 63–72.Google Scholar
  32. 32.
    Bader, R. F. W. Atoms in Molecules. A Quantum Theory; Oxford University Press, 1990.Google Scholar
  33. 33.
    Klooster, W. T.; Swaminathan, S.; Nanni, R.; Craven, B. M. Acta Cryst. 1992, B48, 217–227.Google Scholar
  34. 34.
    Flensburg, C.; Larsen, S.; Stewart, R. F. J. Phys. Chem. 1995, 99, 10130–10141.Google Scholar
  35. 35.
    Howard, S. T. Unpublished topological analysis of 2-methyl-4-nitroaniline.Google Scholar
  36. 36.
    Bader, R. F. W.; Cheng, C. J. Phys. Chem. 1989, 93, 2946–2956.Google Scholar
  37. 37.
    Bader, R. F. W.; Laidig, K. E. In The Application of Charge Density Research to Chemistry and Drug Design. Jeffrey, G. A.; Piniella, J. F., eds.; Nato ASI series B. Physics, vol. 250. Plenum Press: New York, 1991.Google Scholar
  38. 38.
    Gillespie, R. J.; Robinson, E. A. Angewandte Chemie 1996, 35, 495–514.Google Scholar

Copyright information

© Plenum Publishing Corporation 1998

Authors and Affiliations

  • Anna Puig-Molina
    • 1
  • Angel Alvarez-Larena
    • 1
  • Juan F. Piniella
    • 1
  • Sean T. Howard
    • 2
  • François Baert
    • 3
  1. 1.Area de Cristallografia i Mineralogia. Dept. de GeologiaUniversitat Autònoma de BarcelonaBellaterra, BarcelonaSpain
  2. 2.Department of ChemistryUniversity of Wales, CardiffCardiffUnited Kingdom
  3. 3.Dynam. Struct. Mat. Molec. Lab.Université des Sciences et Technologies de LilleVilleneuve D'AscqFrance

Personalised recommendations