Journal of Chemical Crystallography

, Volume 27, Issue 9, pp 499–505 | Cite as

Structural investigation of 1-amino-2,4,6-trinitrobenzenes in the solid state and in solution

  • Ricardo Baggio
  • M. Virginia Remedi
  • María Teresa Garland
  • Elba I. Buján
Article

Abstract

The crystal structure of 1-pyrrolidino-2,4,6-trinitrobenzene3, 1-morpholino-2,4,6-trinitrobenzene4 and 1-piperidino-2,4,6-trinitrobenzene5 have been determined by single-crystal X-ray diffraction data and the structure in solution was investigated by UV-visible spectrophotometry and13C nmr. The three compounds are monoclinic, space groupP2i/n. Unit cell dimensions area=6.6660(1),b=8.612(1),c=20.696(3) Å, β=90.73(1)o, andDc=1.58 g cm−3 for compound3;a=7.090(2),b=21.493(9),c=8.298(3) Å, β=101.27(1)o, andDc 1.60 g cm−3 for compound4 anda=10.426(1),b=10.038(1),c=12.291(1) Å, β=90.04(1)o withDc=1.53 g cm−3 for compound5 forZ=4. In the solid state, differences regarding the planarity of the aromatic ring in the three substrates were found. Rotation of theortho-nitro groups and of the amino group out of the aromatic plane was observed both in the solid state and in the solution. Greater coplanarity of the two rings was found in3 than in4 and5.

Key words

1-Amino-2,4,6-trinitrobenzenes structural determination spectroscopic study 

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References

  1. 1.(a)
    de Rossi, R.H.; de Vargas, E.B.,J. Am. Chem. Soc. 1981,103, 1533. (b) de Vargas, E.B.; de Rossi, R.H.Tetrahedron Lett. 1982,43, 4423. (c) de Vargas, E.B.; de Rossi, R.H.J. Org. Chem. 1984,49, 3978. (d) de Vargas, E.B.; de Rossi, R.H.; Veglia, A.V.J. Org. Chem. 1986,51, 1976. (e) de Vargas, E.B.; de Rossi, R.H.J. Phys. Org. Chem. 1989,2, 507. (d) Buján de Vargas, E.B.; Remedi, M.V.; de Rossi, R.H.J. Phys. Org. Chem. 1995,8, 113.CrossRefGoogle Scholar
  2. 2.
    Sheldrick, G.M.:SHELXS86. Program for the Solution of Crystal Structures; University of Göttingen: Germany,1986.Google Scholar
  3. 3.
    Sheldrick, G.M.:SHELXL93. Program for Structure Refinement; University of Göttingen: Germany,1993.Google Scholar
  4. 4.
    Nardelli, M.,Comp. Chem. 1983,7, 95.CrossRefGoogle Scholar
  5. 5.
    Sheldrick, G.M.:SHELXTL-PC. Version 4.2; Siemens. Analytica X-ray Instruments, Inc.; Madison, WI,1991.Google Scholar
  6. 6.
    Cremer, D.; Pople, J.A.,J. Am. Chem. Soc. 1975,97, 1354.CrossRefGoogle Scholar
  7. 7.
    Kamlet, M.J.; Adolph, H.G., Hoffsommer, J.C.J. Am. Chem. Soc. 1964,86, 4018.CrossRefGoogle Scholar
  8. 8.(a)
    Punte, G.; Rivero, B.; Socolovsky, S.E.; Nudelman, N.S.Acta Crystallogr. 1989,C45, 1952. (b) Punte, G.; Rivero, B.; Socolovsky, S.E.; Nudelman, N.S.Acta Crystallogr. 1991.C47, 1222.Google Scholar
  9. 9.
    Rao, C.N.R.,Espectroscopía Ultravioleta y Visible; spanish version by Castaño. Almendral, F., Ed.; Alhambra; Madrid,1970.Google Scholar
  10. 10.
    Pretsch, E.; Clerc, T.; Seibl, J.; Simon, W.Tablas para la Elucidación Estructural de Compuestos Orgánicos por Métodos Espectroscópicos; Spanish version by Casells, J.; Camps, F., Ed.; Alhambra: Mardrid,1980.Google Scholar
  11. 11.(a)
    Sekiguchi, S.; Hosokawa, M.; Suzuki, T.; Sato, M.J. Chem. Soc. Perkin Trans. 2 1993, 1111Google Scholar
  12. 11.(b)
    Nyburg, S.C.; Faerman, C.H.; Prasad, L.; Palleros, D.; Nudelman, N.S.,Acta Crystallogr. 1987,C43(4) 686.Google Scholar
  13. 12.
    Buján de Vargas, E.; Remedi, M.V.Atualidades de Físicoquímica Orgânica 1995, 404.Google Scholar

Copyright information

© Plenum Publishing Corporation 1997

Authors and Affiliations

  • Ricardo Baggio
    • 1
  • M. Virginia Remedi
    • 2
  • María Teresa Garland
    • 3
  • Elba I. Buján
    • 2
  1. 1.Departamento de FísicaComisión Nacional de Energía AtómicaBuenos AiresArgentina
  2. 2.Instituto de Investigaciones en Fisicoquimica de Córdoba, INFIQC, Departamento de Química Orgánica, Facultad de Ciencias QuímicasUniversidad Nacional de CórdobaCórdobaArgentina
  3. 3.Departamento de Física, Facultad de Ciencias Físicas y MatemáticasUniversidad de ChileSantiagoChile

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