Skip to main content
SpringerLink
Log in

Strychnine-8-ammonio-2-naphthalenesulfonate-water (1/1/3.5): The first structure of a strychnine or brucine compound with a zwitterionic species

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

 

The crystal structure of the 1:1 adduct hydrate of strychnine with 1,7-Cleve's acid (8-amino-2-naphthalenesulfonic acid), namely strychnine-8-ammonio-2-naphthalenesulfonate-water (1/1/3.5) has been determined and provides a unique example of a neutral association involving strychnine and an achiral zwitterionic acid species, previously unobserved in the structures of either strychnine or brucine addition compounds. Crystals are orthorhombic, space group P212121, with Z=4 in a cell with dimensions a=10.4484(8), b=30.850(3), c=9.4998(11) Å. Hydrogen bonding involving all available proton-donor and acceptor sites on all species gives rise to a three-dimensional framework polymer structure. The crystallographic literature for strychnine and brucine and their compounds is also reviewed.

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

Fig. 1.
Fig. 2.

Similar content being viewed by others

References

  1. Fischer, E. Ber. 1899, 32, 2451.

    CAS  Google Scholar 

  2. Holmes, H.L. In The Alkaloids, vol. II, Manske R.H.F.; Holmes, H.L., Eds.; Academic: New York, 1952; p. 514.

  3. Briggs, L.H.; Openshaw, H.T.; Robinson, R. J. Chem. Soc. 1946, 903; Woodward, R.B.; Brehm, W.J.; Nelson, A.L. J. Am. Chem. Soc. 1947, 69, 2250.

  4. Robertson, J.H.; Beevers, C.A. Acta Crystallogr. 1951, 4, 270.

    Article  CAS  Google Scholar 

  5. Bokhoven, C.; Schoone, J.C.; Bijvoet, J.M. Acta Crystallogr. 1951, 4, 475 (sulfate); Mostad, A. Acta Chem. Scand., Sect. B. 1985, 39, 705 (nitrate); R. Ghosh; Roychowdhury, P.; Chattopadhyay, D.; Iitaka, Y. Acta Crystallogr. 1989, C45, 1794 (chloride); Yuan, H.S.H.; Stevens, R.C.; Bau, R.; Mosher, H.S.; Koetzle, T.F. Proc. Nat. Acad. Sci. U.S.A. 1994, 91, 12872 (iodide); Bottcher, P.; Buchkremer-Hermans, H. Z. Naturforsch. B, Chem. Sci. 1987, 42, 431 (hexasulfide); Bialońska, A.; Ciunik, Z. Acta Crystallogr. 2005, C61, o161 (perchlorate, hydrogen sulfate, dihydrogenphosphate); Bialońska, A.; Ciunik, Z. Acta Crystallogr. 2005, E61, o4222 (brucinium sulfate heptahydrate).

  6. Smith, G.; Wermuth, U.D.; Healy, P.C.; White, J.M, Acta Crystallogr. 2006, C62, o203 [brucine-H2O (1/4) and (1/5.25)], Glover, S.S. B; Gould, R.O.; Walkinshaw, M.D. Acta Crystallogr. 1985, C41, 990 [strychnine; brucine-EtOH-H2O (1/1/2)]; Mostad, A. Acta Chem. Scand. B, 1985, 39, 705 (strychnine); Bialońska, A.; Ciunik, Z. Acta Crystallogr., 2004, C60, o853 [brucine; brucine-PriOH-H2O (1/1/2); brucine-Me2CO (1/1)]; Sake Gowda, D.S.; Cartz, L.; Natarajan, S. Acta Crystallogr., 1973, B29, 2760 (strychnine sulfonate); Mostad, A. Acta Chem. Scand. B 1986, 306, 64 (20,21-dihydrostrychnine); Mostad, A. Acta Chem. Scand. A 1988, 42, 391 (pseudostrychnine); Beddoes, R.L.; Gorman, A.A.; Prescott, A.L. Acta Crystallogr. 1994, C50, 447 (neostrychnine); Maurin, J.K.; Lis, T.; Zawadzka, A.; Czarnocki, Z. Acta Crystallogr. 2006, E62, o694 (strychnidine hydrogen succinate).

  7. Gould, R.O.; Kelly, R; Walkinshaw, M.D. J. Chem. Soc., Perkin Trans. 2 1984, 847; Gould, R. O; Walkinshaw, M.D. J. Am. Chem. Soc. 1984, 106, 7840 (N-benzoyl-D- and L-alanines); Bialońska, A.; Ciunik, Z. CrystEngComm 2004, 6, 276 (N-phthaloyl-D- and –L-alanines); Gould, R.O.; Taylor, P.; Walkinshaw, M.D. Acta Crystallogr. 1987, C43, 2405 (N-acetyl-L-tryptophane); Kuwata, S.; Tanaka, J.; Onda, N.; Yamada, T.; Miyazawa, T.; Sugiura, M.; In, Y.; Doi, M.; Inoue, M.; Ishida, T. Bull. Chem. Soc. Jap. 1993, 66, 1501 (N-phthaloyl-α-hydroxy-D- and L-leucines), Biolonska, A.; Ciunik, Z. CrystEngComm. 2006, 8, 640 [N-(5-nitrobenzoyl-and N-(3, 5-dinitrobenzoyl)-D- and L-ananines].

  8. Gould, R.O.; Taylor, P.; Walkinshaw, M.D.; Bruins Slot, H.J. Acta Crystallogr. 1987, C43, 2405 (D- and L-tartaric acids with strychnine); Smith, G.; Wermuth, U.D.; White, J.M. Acta Crystallogr. 2006, C62, o353. (L-malic and L-tartaric acids with brucine); Dijksma, F.J.J.; Gould, R.O.; Parsons, S.; Taylor, P.; Walkinshaw, M.D. Chem. Commun. 1998, 745 (α,β-D-glucuronic and α,β-D-galacturonic acids); Gould, R.O.; Walkinshaw, M.D.; Wimmer, N.; Kosma, P. Acta Crystallogr. 2002, A58, C-126 (a disaccharide acid); Quinkert, G.; Schmalz, H. –G; Dzierzynski, E.M.; Durner, G.; Batz, J.W. Angew. Chem. Int. Ed. Engl. 1986, 25, 992([(-)-jasmonate methyl ester]; Wright, J.L.; Caprathe, B.W.; Downing, D.M.; Glase, S.A.; Heffner, T.G.; Jaen, J.C.; Johnson, S.J.; Kesten, S.R.; MacKenzie, R.G.; Meltzer, L.T.; Pugsley, T.A.; Smith, S.J.; Wise, L.D.; Wustrow, D.J. J. Med. Chem. 1994, 151, 3523 (3-oxocyclohexanecarboxylic acid); Krajewski, K.; Ciunik, Z. Pol. J. Chem. 1999, 73, 1687 [(+)-cyclohexene-1-carboxylic acid]; Andersson, M.; Sundell, S.; Allenmark, S. Enantiomer 1999, 4, 411 [(+)-Z-ethylsulfinyl-but-2-enoic acid]; Allenmark, S.; Skogsberg, U. Enantiomer 2000, 5, 451 (Z-acenaphthalen-1,2-dicarboxylic acid); Boiadjiev, S.E.; Person, R.V.; Puzicha, G.; Knobler, C.; Maverick, E.; Trueblood, K.N.; Lightner, D.A. J. Am. Chem. Soc. 1992, 114, 10123 [(+)-(S)-3-{2,4-dimethyl-5-(ethoxycarbonyl)-1H-pyrrol-3-yl}butanoic acid]; Costente, J.; Ehlinger, E.; Perrin, M; Collett, A. Enantiomer 1996, 1, 377 [(+)-bromochlorofluoroacetic acid]; Yuan, H.S.H.; Stevens, R.; Bau, R.C.; Mosher, H.S.; Koetzle, T.F. Proc. Nat. Acad. Sci. U.S.A. 1994, 91, 12872 (a phthalolyl-substituted neopentylcarboxylic acid); Laursen, J.B.; Jorgensen, C.G.; Nielsen, J. Biorg. Med. Chem. 2003, 11, 723 [(-)-(R)-saphenic acid]; Bialońska, A.; Ciunik, Z.; Popek, T.; Lis, T. Acta Crystallogr. 2005, C61, o88 (L-glyceric acid); Berkman, C.F.; Fernandez, E.J.; Thompson, C.M.; Pavkovic, S.F. Acta Crystallogr. 1993, C49, 554 (a phosphodithiol, with 19-methylstrychnine).

  9. Toda, F.; Tanaka, K.; Ueda, H. Tetrahedron Lett. 1981, 22, 4669 [1-(2-bromophenyl)-1-phenyl-2-propyn-1-ol]; Toda, F.; Tanaka, K.; Ueda, H.; Oshima, T. Israel J. Chem. 1985, 25, 338 (3-methyl-1-penten-3-ol); Tanaka, K.; Kato, M.; Toda, F. Heterocycles 2001, 54, 405 (2-azabicyclo[2.2.1]hept-5-en-3-one); Chandramohan, K.; Ravikumar, K. J. Chem. Cryst. 1999, 29, 121 (pantolactone); Yamagishi, M.; Yamada, Y.; Ozaki, K.; Da-te, T.; Okamura, K.; Suzuki, M.; Matsumoto, K. J. Org. Chem. 1992, 57, 1568 [(+)-3-methylspiro[imidazolidine-4,4’-(1’H)-quinazoline-2,2’,5-(3’H)-trione]; Pinkerton, A.A.; Carrupt, P. –A; Claret, F.; Vogel, P. Acta Crystallogr. 1993, C49, 1632 (2-hydroxybicyclo[2.2.1]hept-5-ene-2-carbonitrile and 2-hydroxy-7-oxabicyclo[2.2.1]hept-5-ene-2-carbonitrile); Lineberry, A.M.; Wheeler, K.A. Acta Crystallogr. 2006, E62, o3870 [(s)-2=(2-bromophenoxy)propionic acid (with strychnine)].

    Google Scholar 

  10. Oshikawa, T.; Pochamroen, S.; Takai, N.; Ide, N.; Takemoto, T.; Yamashita, M. Heterocyclic Commun. 2002, 8, 271 (3-nitrobenzoic acid).

  11. Sada, K.; Yoshikawa, K.; Miyata, M. Chem. Commun. 1998, 1763 (4-hydroxybenzoic acid); Guo, W. -S.; Guo, F.; Deng, M.; Ge, C. –H.; Liu, Q. –T.; Hua, X. –Q.; Bai, J. –L.; Tian, Z. –Y.; Wang, S. –C.; Zheng, Q. –T. Huaxue Xuebao 2001, 59, 284 (4-nitrophenol); Dijksma, F.J. J.; Gould, R.O.; Parsons, S.; Walkinshaw, M.D. Acta Crystallogr. 1998, C54, 1948 (fumaric and maleic acids); Bao, J.; Wulff, W.D.; Dominy, J.B.; Fumo, M.J.; Grant, E.B.; Rob, A.C.; Whitcomb, M.C.; Yeung, S. –M.; Ostrander, R.L.; Rheingold, A.L. J. Am. Chem. Soc. 1996, 118, 3392 [2,2’-bis(3-phenyl-1-naphthol)phosphoric acid]; Cheung, E.; Netherton, M.R.; Scheffer, J.R.; Trotter, J. Tetrahedron Lett. 1999, 40, 8733 (2,2-dimethyl-1-oxonaphthalene-4-carboxylic acid).

  12. Smith, G.; Wermuth, U.D.; Healy, P.C.; White, J.M. Acta Crystallogr. 2006, C62, o537.

  13. Smith, G.; Wermuth, U.D.; Young, D.J.; Healy, P.C. Acta Crystallogr. 2005, E61, o2008.

    CAS  Google Scholar 

  14. Smith, G.; Wermuth, U.D.; Healy, P.C.; Young, D.J.; White, J.M. Acta Crystallogr. 2005, E61, o2646.

    CAS  Google Scholar 

  15. Smith, G.; Wermuth, U.D.; White, J.M. Acta Crystallogr. 2005, C61, o464.

    CAS  Google Scholar 

  16. Smith, G.; Wermuth, U.D.; Young, D.J.; White, J.M. Acta Crystallogr. 2004, E60, o2010.

    Google Scholar 

  17. Huffman, C.W.; Skelly, W.G. Chem. Rev. 1960, 63, 625; Radke, F.H.; Fearing, R.B.; Fox, S.W. J. Am. Chem. Soc. 1954, 86, 2801.

  18. Ravishankar, R.; Chandra, N.R.; Vijayan, M. J. Biomet. Struct. Dynamics 1998, 18, 1093 (L- and DL-arginine with maleic acid); Alagar, M.; Krishnakumar, R.V.; Rajagopal, K.; Nandhini, M.; Natarajan, K. Acta Crystallogr. 2003 , E59, o952 (L-phenylalanine with fumaric acid); Alagar, M.; Krishnakumar, R.V.; Subha Nandhini, M.; Natarajan, K. Acta Crystallogr. 2003 , E59, o857 (DL-valine with fumaric acid).

  19. Altomare, A.; Cascarno, G.; Giocovasso, C.; Guagliardi, A.; Burla, M.C.; Polidori, G.; Camalli, M. J. Appl. Crystallogr. 1994, 27, 435.

    Article  Google Scholar 

  20. Sheldrick, G.M. SHELXL 97: Program for Crystal Structure Refinement, University of Göttingen, Germany.

  21. TeXsan for Windows: Structure Analysis Software. Version 1.06, 1999. Molecular Structure Corporation, New Trails Drive, The Woodlands, TX77381, USA.

  22. Peerdeman, A.F. Acta Crystallogr. 1956, 9, 824.

    Article  CAS  Google Scholar 

  23. Eliel, E.L. Stereochemistry of Carbon Compounds, McGraw-Hill: New York, 1962, pp. 92–94.

    Google Scholar 

  24. Spek, A.L. PLATON: A Multipurpose Crystallographic Tool. J. Appl. Crystallogr. 2003, 36, 7.

    Google Scholar 

  25. Flack, H.D. Acta. Crystallogr. 1983, A39, 876.

    CAS  Google Scholar 

Download references

Acknowledgments

The authors acknowledge financial support from the School of Physical and Chemical Sciences (Queensland University of Technology) and Griffith University.

Author information

Authors and Affiliations

  1. School of Physical and Chemical Sciences, Queensland University of Technology, G.P.O. Box 2434, Brisbane, Qld. 4001, Australia

    Graham Smith & Urs D. Wermuth

  2. School of Science, Griffith University, Nathan, Qld. 4111, Australia

    Peter C. Healy & David J. Young

Authors
  1. Graham Smith
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Urs D. Wermuth
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Peter C. Healy
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. David J. Young
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Graham Smith.

Additional information

Supplementary material

CCDC 254727 contains supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/data request/cif by e-mailing datarequest@ccdc.cam.ac.uk, or contacting The Cambridge Crystallographic Data Centre, 12 Union Road, CambridgeCB2 1EZ.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Smith, G., Wermuth, U.D., Healy, P.C. et al. Strychnine-8-ammonio-2-naphthalenesulfonate-water (1/1/3.5): The first structure of a strychnine or brucine compound with a zwitterionic species. J Chem Crystallogr 36, 805–811 (2006). https://doi.org/10.1007/s10870-006-9085-5

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10870-006-9085-5

KEY WORDS:

Search

Navigation