Skip to main content
SpringerLink
Log in

The utility of 4-aminobenzoic acid in promotion of hydrogen bonding in crystallization processes: the structures of the cocrystals with halo and nitro subsituted aromatic compounds, and the crystal structures of the adducts with 4-nitroaniline (1:1), 4-(4-nitrobenzyl)pyridine (1:2), and (4-nitrophenyl)acetic acid (1:1)

  • Published:
Journal of Chemical Crystallography Aims and scope Submit manuscript

Abstract

A number of molecular adducts of 4-aminobenzoic acid (4-ABA) have been prepared and characterized using infrared spectroscopy and in three cases by X-ray diffration methods. These three compounds are with 4-nitroaniline [(4-ABA) (C6H6N2O2)], 4-(4-nitrobenzyl) pyridine, [(4-ABA)2(C12H10N2O2)4], and (4-nitrophenyl)acetic acid, [(4-ABA) (C8H7NO4)]. Other compounds described are with 4-chlorobenzoic acid, [(4-ABA) (C7H5ClO2)], 4-bromobenzoic acid, [(4-ABA) (C7H5BrO2)], 4-cyanobenzoic acid, [(4-ABA) (C7H6N2)], 2-nitrobenzoic acid, [(4-ABA) (C7H5NO4)], and 3-nitrobenzoic acid, [(4-ABA) (C7H5NO4)]. All compounds have 1:1 stoichiometry except that with 4-(4-nitrobenzyl)pyridine (1:2) which is unique in being retro-stoichiometric. A review of the systematics of the 4-aminobenzoic acid adducts is also made, particularly with respect to the infrared characterization of the cocrystalline materials and prediction of their NLO potential.

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. Lechat, J.;Acta Crystallog. Sect. A. 1984,40,C-264.

    Article  Google Scholar 

  2. Ueda, M.; Onishi, H.; Nagu, T.Acta Crystallogr. Sect C 1986,42, 462.

    Article  Google Scholar 

  3. Etter, M.C.; Frankenbach, G.M.Chem. Mater. 1989,1, 10.

    Article  CAS  Google Scholar 

  4. Elbasyouny, A.; Brugge, H.J.; von Deuten, K; Dickel, M.; Knochel, A.; Koch, K.U.; Kopf, J.; Melzer, D.; Rudolph, G.J. Am. Chem. Soc. 1982,105, 6568.

    Article  Google Scholar 

  5. Lynch, D.E.; Smith, G.; Byriel, K.A.; Kennard, C.H.L.Z. Kristallogr. 1992,200 73

    Article  CAS  Google Scholar 

  6. Byriel, K.A.; Lynch, D.E.; Smith, G.; Kennard, C.H.L.Aust. J. Chem. 1991,44, 1459.

    Article  CAS  Google Scholar 

  7. Lynch, D.E.; Smith, G.; Byriel, K.A.; Kennard, C.H.L.; Whittaker, A.K.Aust. J. Chem. 1994,47, 309.

    Article  CAS  Google Scholar 

  8. Lynch, D.E.; Smith, G.; Byriel, K.A.; Kennard, C.H.L.Acta Crystallogr. Sect. C 1992,45, 535.

    Google Scholar 

  9. Smith, G.; Lynch, D.E.; Byriel, K.A.; Kennard, C.H.L.Aust. J. Chem. 1995,48, 1133.

    Article  CAS  Google Scholar 

  10. Etter, M.C.Acc. Chem. Res. 1990,23, 120.

    Article  CAS  Google Scholar 

  11. Lai, T.F.; Marsh, R.E.Acta Crystallogr. 1967,22, 885.

    Article  CAS  Google Scholar 

  12. Etter, M.C.; Adsmond, D.A.J. Chem. Soc., Chem. Commun. 1990,300; Etter, M.C.; Adsmond, D.A.; Britton, D.Acta Crystallogr. Sect. C. 1990,46, 933.

  13. Lynch, D.E.; Smith, G.; Freney, D.; Byriel, K.A.; Kennard, C.H.L.Aust. J. Chem. 1994,47, 1097.

    Article  CAS  Google Scholar 

  14. Caira, M.R.J. Cryst. Spectrosc. 1991,21, 641.

    Article  CAS  Google Scholar 

  15. Stecher, P.G.,The Merck Index (8th Ed.),Merck and Co. Inc., Rahway, NJ,1968, p 53.

    Google Scholar 

  16. Lynch, D.E.; Smith, G.; Byriel, K.A.; Kennard, C.H.L.Acta crystallogr. Sect. C. 1994,50, 2079.

    Article  Google Scholar 

  17. Lynch, D.E.; Smith, G.; Byriel, K.A.; Kennard, C.H.L.J. Chem. Soc. Chem. Commun. 1992, 300.

  18. Coffey, S.Rodd's chemistry of carbon compounds, Vol. III; Elsevier, Amsterdam,1977, p 48.

    Google Scholar 

  19. Etter, M.C.; Frankenbach, G.M.; Adsmond, D.A.Mol. Cryst. Liq. Cryst. 1990,187, 25.

    CAS  Google Scholar 

  20. Etter, M.C. (private communication).

  21. Sharma, C.V.K.; Panneerselvam, K.; Pilati, T.; Desiraju, G.R.J. Chem. Soc. Perkin Trans. 1993,2, 2209.

    Google Scholar 

  22. Etter, M.C.; Huang, K.S.; Frankenbach, G.M.: Adsmond, D.A. inMaterials for nonlinear optics; Marder, S.R.; Sohn, J.E.; Stucky, G.P., Eds ACS Symposium Series No. 445, American Chemical Society,1991; pp 445–456.

  23. Bernstein, J.; Etter, M.C.; Leiserowitz, L. inStructure correlation vol. 2. Burgi, H.-B.; Dunitz, J.D., Eds.: VCH: Weinheim, FRG1994, pp 431–507.

    Google Scholar 

  24. Smith, G.; Lynch, D.E.; Byriel, K.A.; Kennard, C.H.L.Acta Crystallogr. Sect. C 1996,52, 231.

    Article  Google Scholar 

  25. Sheldrick, G.M.SHELXS-86, Structure Solution Package, University of Göttingen, Federal Republic of Germany,1986.

    Google Scholar 

  26. Sheldrick, G.M.,SHELXL-93, program for crystal structure determination: University of Göottingen Federal Republic of Germany,1993.

    Google Scholar 

  27. Johnson, S.L.; Rumon, K.A.;J. Phys. Chem. 1965,69, 74.

    CAS  Google Scholar 

  28. Berkovich-Yellin, Z.; Leiserowitz, L.Acta Crystallogr. Sect. B 1984,40, 159.

    Article  Google Scholar 

  29. Williams, D.H.; Fleming I.,Spectroscopic methods in organic chemistry (2nd ed.); McGraw-Hill, London,1973, pp 35–73.

    Google Scholar 

  30. Lynch, D.E.; Smith, G.; Byriel, K.A.; Kennard, C.H.L.,Aust. J. Chem. 1994,47, 1789.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. School of Physical Sciences, Queensland University of Technology, P.O. Box 2334, 4001, Brisbane, Australia

    Graham Smith

  2. School of Natural and Environmental Sciences, Coventry University, CV1 5FB, Coventry, UK

    Daniel E. Lynch

  3. Department of Chemistry, The University of Queensland, 4072, Brisbane, Australia

    Karl A. Byriel & Colin H. L. Kennard

Authors
  1. Graham Smith
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Daniel E. Lynch
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Karl A. Byriel
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Colin H. L. Kennard
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

Smith, G., Lynch, D.E., Byriel, K.A. et al. The utility of 4-aminobenzoic acid in promotion of hydrogen bonding in crystallization processes: the structures of the cocrystals with halo and nitro subsituted aromatic compounds, and the crystal structures of the adducts with 4-nitroaniline (1:1), 4-(4-nitrobenzyl)pyridine (1:2), and (4-nitrophenyl)acetic acid (1:1). J Chem Crystallogr 27, 307–317 (1997). https://doi.org/10.1007/BF02575979

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02575979

Key words

Search

Navigation