Hydrogen bonding in nitrofurantoin polymorphs: A computation-assisted spectroscopic study

Journal of Raman Spectroscopy

Volumn 40, Issue 12, 2009, Pages 1956-1965

  Sardo, Mariana ^a   Amado, Ana M ^b   Ribeiro Claro, Paulo J A ^a  

^a UNIVERSITY OF AVEIRO   (Portugal)

^b UNIVERSITY OF COIMBRA   (Portugal)

Author keywords

DFT calculations; Hydrogen bonds; Nitrofurantoin; Polymorphism; Vibrational spectroscopy

Indexed keywords

ASSOCIATION REACTIONS; DENSITY FUNCTIONAL THEORY; POLYMORPHISM; SPECTROSCOPIC ANALYSIS;

DFT CALCULATION; HYDROGEN-BOND FORMATION; INTERMOLECULAR HYDROGEN BONDS; MOLECULAR ASSOCIATIONS; MOLECULAR PACKINGS; NITROFURANTOIN; RAMAN AND INFRARED SPECTRA; SPECTROSCOPIC DATA; SPECTROSCOPIC STUDIES; VIBRATIONAL MODES;

HYDROGEN BONDS;

EID: 72249083568     PISSN: 03770486     EISSN: 10974555     Source Type: Journal    
DOI: 10.1002/jrs.2346     Document Type: Article

References (34)

1. M. M. Nolasco, A. M. Amado, P. J. A. Ribeiro-Claro, ChemPhysChem 2006,7,2150.
2. M. Schmitt, J. Popp, J. Raman Spectrosc. 2006, 37, 20.
3. M.M. Nolasco, A.M. Amado, P.J.A. Ribeiro-Claro, J. RamanSpectrosc. 2009,40,394.
4. R. P. Tangallapally, R. Yendapally, R. E. Lee, K. Hevener, V. C. Jones, A. J. M. Lenaerts, M. R. McNeil, Y. Wang, S. Franzblau, R. E. Lee, J. Med. Chem. 2004, 47, 5276.
5. R. Eyjolfsson, Drug Dev. Ind. Pharm. 1999, 25, 105.
6. E. W. Pienaar, M. R. Caira, A. P. Lötter, J. Crystallogr. Spectrosc. Res. 1993,23,785.
7. M. R. Caira, E. W. Pienaar, A. P. Lötter, Mol.Cryst.Liq.Cryst.1996,279, 241.
8. M. Karjalainen, S. Airaksinen, J. Rantanen, J. Aaltonen, J. Yliruusi, J. Pharm. Biomed. Anal. 2005, 39, 27.
9. V. Bertolasi, P. Gilli, V. Ferretti, G. Gilli, Acta Crystallogr. 1993, C49, 741.
10. P. V. Marshall, P. York, Int. J. Pharm. 1989, 55, 257.
11. J. Bernstein, Polymorphism in Molecular Crystals, Oxford University Press: Oxford, 2002.
12. H. G. Brittain, J. Pharm. Sci. 1997, 86, 405.
13. G. Fini, J. Raman Spectrosc. 2004, 35, 335.
14. A. Burger, Pharm. Int. 1983, 4, 186.
15. M. R. Caira, Design of Organic Solids 1998, 198, 163.
16. J. Haleblian, W. McCrone, J. Pharm. Sci. 1969, 58, 911.
17. J. D. Dunitz, J. Bernstein, Acc. Chem. Res. 1995, 28, 193.
18. N. V. Phadnis, R. Suryanarayanan, J. Pharm. Sci. 1997, 86, 1256.
19. F. Giordano, A. Gazzaniga, J. R. Moyano, P. Ventura, M. Zanol, T. Peveri, L. Carima, J. Pharm. Sci. 1998, 87, 333.
20. N. A. Marigheto, E. K. Kemsley, J. Potter, P. S. Belton, R. H. Wilson, Spectrochim. Acta, Part A 1996, 52, 1571.
21. J. Johansson, S. Pettersson, L. S. Taylor, J.Pharm.Biomed.Anal.2002, 30,1223.
22. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery Jr, T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al- Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, J. A. Pople, R. B. Gaussian 03, Gaussian, Inc.: Pittsburgh, PA, 2003.
23. C. Lee, W. Yang, R. G. Parr, Phys. Rev. B 1988, 37, 785.
24. A. Becke, J. Chem. Phys. 1993, 98, 5648.
25. P. C. Hariharan, J. A. Pople, Theor. Chim. Acta 1973, 28, 213.
26. A. P. Scott, L. Radom, J. Phys. Chem. B 1996, 100, 16502.
27. G. Bandoli, A. Ongaro, F. Lotto, M. Rossi, Powder Differ. 1993, 8, 107.
28. A. Gavezzotti, J. Phys. Chem. B 2002, 106, 4145.
29. J. D. Dunitz, A. Gavezzotti, Angew. Chem., Int. Ed. Engl. 2005, 44, 1766.
30. V. Bertolasi, V. Ferretti, G. Gilli, P. A. Borea, J.Chem.Soc.,PerkinTrans. 1990,2,283.
31. G. A. Jeffrey, W. Saenger, Hydrogen Bonding in Biological Structures, Springer-Verlag: Berlin, 1991.
32. M. M. Nolasco, P. J. A. Ribeiro-Claro, ChemPhysChem 2005, 6, 496.
33. P. J. A. Ribeiro-Claro, M. G. B. Drew, V. Félix, Chem. Phys. Lett. 2002, 356,318.
34. P. J. A. Ribeiro-Claro, M. P. M. Marques, A. M. Amado, Chem Phys Chem 2002, 3, 599.