Vibrational spectroscopic studies of cocrystals and salts. 3. cocrystal products formed by benzenecarboxylic acids and their sodium salts

Crystal Growth and Design

Volumn 10, Issue 4, 2010, Pages 1990-2003

  Brittain, Harry G ^a  

^a Center for Pharmaceutical Physics   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 77950839910     PISSN: 15287483     EISSN: 15287505     Source Type: Journal    
DOI: 10.1021/cg100099w     Document Type: Article

References (30)

1. Brittain, H. G. Vibrational Spectroscopic Studies of Cocrystals and Salts. 2. The Benzylamine'Benzoic Acid System Cryst. Growth Des. 2009, 9, 3497-3503
2. Childs, S. L.; Chyall, L. J.; Dunlap, J. T.; Smolenskaya, V. N.; Stahly, B. C.; Stahly, G. P. Crystal Engineering Approach to Forming Cocrystals of Amine Hydrochlorides with Organic Acids. Molecular Complexes of Fluoxetine Hydrochloride with Benzoic, Succinic, and Fumaric Acids J. Am. Chem. Soc. 2004, 126, 13335-13342
3. Metrangolo, P.; Pilati, T.; Terraneo, G.; Biella, S.; Resnati, G. Anion Coordination and Anion-Templated Assembly under Halogen Bonding Control CrystEngComm 2009, 11, 1187-1196
4. Pop, M.; Sieger, P.; Cains, P. W. Tiotropium Fumarate: An Interesting Pharmaceutical Cocrystal J. Pharm. Sci. 2009, 98, 1820-1834
5. Vishweshwar, P.; McMahon, J. A.; Bis, J. A.; Zaworotko, M. J. Pharmaceutical Cocrystals J. Pharm. Sci. 2006, 95, 499-516
6. Trask, A. V. An Overview of Pharmaceutical Cocrystals as Intellectual Property Mol. Pharmaceutics 2007, 4, 301-309
7. Stahly, G. P. Diversity in Single' and Multiple'Component Crystals: The Search for and Prevalence of Polymorphs and Cocrystals Cryst. Growth Des. 2007, 7, 1007-1026
8. Shan, N.; Zaworotko, M. J. The Role of Cocrystals in Pharmaceutical Science Drug Discovery Today 2008, 13, 440-446
9. Brittain, H. G. Vibrational Spectroscopic Studies of Cocrystals and Salts. 1. The Benzamide'Benzoic Acid System Cryst. Growth Des. 2009, 9, 2492-2499
10. Davey, R. J.; Dent, G.; Mughal, R. K.; Parveen, S. Concerning the Relationship between Structural and Growth Synthons in Crystal Nucleation: Solution and Crystal Chemistry of Carboxylic Acids as Revealed through IR Spectroscopy Cryst. Growth Des. 2006, 6, 1788-1796
11. Childs, S. L.; Stahly, G. P.; Park, A. The Salt-Cocrystal Continuum: the Influence of Crystal Structure on Ionization State Mol. Pharmaceutics 2007, 4, 323-338
12. Szymanski, H. A. Interpreted Infrared Spectra; Plenum Press: New York, 1964.
13. Conley, R. T. Infrared Spectroscopy; Allyn and Bacon: Boston, 1966.
14. Socrates, G. Infrared and Raman Characteristic Group Frequencies, 3 rd ed.; John Wiley & Sons: Chichester, 2001.
15. '1 Proc. R. Soc. London 1953, A216, 247-266
16. '1 Spectrochim. Acta 1956, 8, 249-261
17. González-Sánchez, F. Infrared Spectra of the Benzene Carboxylic Acids Spectrochim. Acta 1958, 12, 17-33
18. Hadži, D.; Pintar, M. The OH In-Plane Deformation and the C'O Stretching Frequencies in Monomeric Carboxylic Acids and their Association Shifts Spectrochim. Acta 1958, 12, 162-168
19. Green, J. S. S.; Kynaston, W.; Lindsey, A. S. The Vibrational Spectra of Benzene Derivatives. I. Nitrobenzene, the Benzoate Ion, Alkali Metal Benzoates and Salicylates Spectrochim. Acta 1961, 17, 486-502
20. Wexler, A. S. Interaction and Intensity Borrowing between Aromatic Ring Stretching and Carboxylate Ion Antisymmetric Stretching Modes in Benzoate Salts Spectrochim. Acta 1967, 23A, 1319-1326
21. 5 and Normal Vibrations of Benzoate Ion Spectrochim. Acta 1978, 34A, 793-800
22. -1; Interscience: New York, 1968.
23. Dollish, F. R.; Fateley, W. G.; Bentley, F. F. Characteristic Raman Frequencies of Organic Compounds; John Wiley & Sons: New York, 1974.
24. Grasselli, J. G.; Snavely, M. K.; Bulkin, B. J. Chemical Applications of Raman Spectroscopy; John Wiley & Sons: New York, 1981.
25. Lewis, I. R.; Edwards, H. G. M. Handbook of Raman Spectroscopy; Marcel Dekker: New York, 2001.
26. Kim, Y.; Machida, K. Vibrational Spectra, Normal Vibrations and Infrared Intensities of Six Isotopic Spectra Benzoic Acids Spectrochim. Acta 1986, 42A, 881-889
27. Pagannone, M.; Fornari, B.; Mattei, G. Molecular Structure and Orientation of Chemisorbed Aromatic Carboxylic Acids: Surface Enhanced Raman Spectrum of Benzoic Acid Adsorbed on Silver Sol Spectrochim. Acta 1987, 43A, 621-625
28. Castro, J. L.; López Ramírez, M. R.; López Tocón, I.; Otero, J. C. Vibrational Spectra of Phenylacetate and Phenylglycinate Ions J. Mol. Struct. 2003, 651'653, 601-606
29. Castro, J. L.; López Ramírez, M. R.; López Tocón, I.; Otero, J. C. Vibrational Study of the Metal-Adsorbate Interaction of Phenylacetic Acid and ±-Phenylglycine on Silver Surfaces J. Coll. Interface Sci. 2003, 263, 357-363
30. Castro, J. L.; López Ramírez, M. R.; Arenas, J. F.; Otero, J. C. Vibrational Spectra of 3-Phenylpropionic Acid and l -Phenylalanine J. Mol. Struct. 2005, 744'747, 887-891