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Identification of a new co-crystal of salicylic acid and benzamide of pharmaceutical relevance

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Abstract

Raman spectroscopy, X-ray powder diffraction/X-ray crystallography and differential scanning calorimetry have been used to study the phenomenon of co-crystal formation in stoichiometric mixtures of salicylic acid with benzamide. Raman spectroscopy was particularly useful for the characterization of the products and was used to determine the nature of the interactions in the co-crystals. It was observed that little change in the vibrational modes associated with the phenyl groups of the respective reactants took place upon co-crystal formation, but changes in intensities of the vibrational modes associated with the amide and the carboxylic acid groups were observed upon co-crystal formation. Several new vibrational bands were identified in the co-crystal which were not manifested in the physical mixture of both components and could be used as diagnostic features of co-crystal formation.

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References

  1. Aakeroy CB, Salmon DJ (2005) Cryst Eng Commun 7:439–448

    Article  Google Scholar 

  2. Morissette SL, Almarsson O, Peterson ML, Remenar JF, Read MJ, Lemmo AV, Ellis S, Cima MJ, Gardner CR (2004) Adv Drug Deliv Rev 56:275–300

    Article  CAS  Google Scholar 

  3. Peterson ML, Hickey MB, Zaworotko MJ, Almarsson O (2006) J Pharm Pharmaceut Sci 9:317–326

    Google Scholar 

  4. Jones W (1997) Organic molecular solids: properties and applications. CRC, New York

    Book  Google Scholar 

  5. Atwood JL, Davies JED, MacNicol DD, Vogtle F (1996) Comprehensive supramolecular chemistry, vol 9. Pergamon, Oxford

    Google Scholar 

  6. Bond AD, Jones W (2002) Supramolecular organization and materials design. Cambridge University Press, Cambridge

    Google Scholar 

  7. Desiraju GR (1989) Crystal engineering: the design of organic solids. Elsevier, New York

    Google Scholar 

  8. Banerjee R, Bhatt PM, Ravindra NV, Desiraju GM (2005) Cryst Growth Des 6:2299–2309

    Article  Google Scholar 

  9. Chiarella RA, Davey RJ, Peterson ML (2007) Cryst Growth Des 7:1223–1226

    Article  CAS  Google Scholar 

  10. Shan N, Zaworotko MJ (2008) Drug Discov Today 13:440–446

    Article  CAS  Google Scholar 

  11. Almarsson O, Zaworotko MJ (2004) Chem Commun 17:1889–1896

    Article  Google Scholar 

  12. Shattock TR, Arora KK, Vishweshwar P, Zaworotko MJ (2008) Cryst Growth Des 8:4533–4545

    Article  CAS  Google Scholar 

  13. Hickey MB, Peterson ML, Scoppettuolo LA, Morrisette SL, Vetter A, Guzman H, Remenar JF, Zhang Z, Tawa MD, Haley S, Zaworotko MJ, Almarssono O (2007) Eur J Pharm Biopharm 67:112–119

    Article  CAS  Google Scholar 

  14. Chadwick K, Davey R, Cross W (2007) Cryst Eng Commun 9:732–734

    Article  CAS  Google Scholar 

  15. Palmer DS, Llinas A, Morao I, Day GM, Goodman JM, Glen RC, Mitchell JBO (2008) Mol Pharm 5:266–279

    Article  CAS  Google Scholar 

  16. Seefeldt K, Miller J, Alvarez-Nunez F, Rodrıguez-Hornedo N (2007) J Pharm Sci 96:1147–1158

    Article  CAS  Google Scholar 

  17. Zhang GGZ, Henry RF, Borchardt TB, Lou XC (2007) J Pharm Sci 96:990–995

    Article  CAS  Google Scholar 

  18. Takata N, Shiraki K, Takano R, Hayashi Y, Terada K (2008) Cryst Growth Des 8:3032–3037

    Article  CAS  Google Scholar 

  19. Bis JA, Vishweshwar P, Middleton RA, Zaworotko MJ (2006) Cryst Growth Des 6:1048–1053

    Article  CAS  Google Scholar 

  20. Fleishman SG, Kuduva SS, McMahon JA, Moulton B, Rosa D, Bailey W, Rodrıguez-Hornedo N, Zaworotko MJ (2003) Cryst Growth Des 3:909–919

    Article  Google Scholar 

  21. Allen FH, Motherwell WDS, Raithby PR, Shields GP, Taylor R (1999) New J Chem 23:25–34

    Article  CAS  Google Scholar 

  22. Arkema S, Bats JW, Weyenberg AM, Feil D (1972) Acta Crystallogr B 28:1646–1648

    Article  Google Scholar 

  23. Leiserowitz L, Nader F (1977) Acta Crystallogr B 33:2719–2733

    Article  Google Scholar 

  24. Reddy LS, Nangia A, Lynch VM (2004) Cryst Growth Des 4:89–94

    Article  CAS  Google Scholar 

  25. Aakeroy CB, Beatty AM, Helfrich BA, Nieuwenhuyzen M (2003) Cryst Growth Des 3:159–165

    Article  Google Scholar 

  26. Vishweshwar P, Nangia A, Lynch VM (2002) J Org Chem 67:556–565

    Article  CAS  Google Scholar 

  27. Vishweshwar P, Nangia A, Lynch VM (2003) Cryst Growth Des 3:783–790

    Article  CAS  Google Scholar 

  28. Allen FA (2002) Acta Crystallogr Sect B 58:380

    Article  Google Scholar 

  29. Aakeroy CB, Beatty AM, Nieuwenhuyzen M, Zou M (2000) Tetrahedron 56:6693–6699

    Article  CAS  Google Scholar 

  30. Childs SL, Stahly GP, Park A (2007) Mol Pharm 4:323–338

    Article  CAS  Google Scholar 

  31. Blake CCF, Small RWH (1972) Acta Crystallogr B 28:2201–2206

    Article  CAS  Google Scholar 

  32. Boczar M, Boda L, Wojcik MJ (2006) Spectrochim Acta Part A 64:757–760

    Article  Google Scholar 

  33. Volovsek V, Colombo L, Furic K (1983) J Raman Spect 14:347–352

    Article  CAS  Google Scholar 

  34. Humbret B, Alnot M, Quiles F (1998) Spectrochim Acta Part A 54:465–476

    Article  Google Scholar 

  35. Kniseley RN, Fassel VA, Farquhar EL, Gray LS (1962) Spectrochim Acta 18:1217–1229

    CAS  Google Scholar 

  36. Smith BC (1998) Infrared spectral interpretation: a systematic approach. CRC, Boca Raton

    Google Scholar 

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Additional Information Available

X-ray crystallographic information for the crystal structures (PDF); this material is available free of charge via the Internet at http://pubs.acs.org. Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication nos. CCDC-756492. Copies of available material can be obtained, free of charge, on application to the Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: + 44 (0) 1223-336033 or e mail: teched@chemcrys.cam.ac.uk).

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Authors and Affiliations

  1. Raman Spectroscopy Group, Division of Chemical and Forensic Sciences, University Analytical Centre, Richmond Road, Bradford, BD7 1DP, UK

    M. A. Elbagerma, H. G. M. Edwards, T. Munshi & I. J. Scowen

Authors
  1. M. A. Elbagerma
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  2. H. G. M. Edwards
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  3. T. Munshi
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  4. I. J. Scowen
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Correspondence to H. G. M. Edwards.

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Elbagerma, M.A., Edwards, H.G.M., Munshi, T. et al. Identification of a new co-crystal of salicylic acid and benzamide of pharmaceutical relevance. Anal Bioanal Chem 397, 137–146 (2010). https://doi.org/10.1007/s00216-009-3375-7

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  • DOI: https://doi.org/10.1007/s00216-009-3375-7

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