Protonation-assisted spontaneous resolution: Formation of a homochiral 2D interpenetrated hydrogen-bonded network from 4,4′-binicotinic acid under highly acidic conditions

CrystEngComm

Volumn 7, Issue , 2005, Pages 297-301

  Custelcean, Radu ^a   Gorbunova, Maryna G ^a  

^a OAK RIDGE NATIONAL LABORATORY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHLORIDE; NICOTINIC ACID DERIVATIVE;

ACIDITY; ARTICLE; CHEMICAL BOND; CHIRALITY; CRYSTAL STRUCTURE; CRYSTALLIZATION; HYDROGEN BOND; MOLECULAR INTERACTION; PROTON TRANSPORT;

EID: 19344373570     PISSN: 14668033     EISSN: 14668033     Source Type: Journal    
DOI: 10.1039/b501901j     Document Type: Article

References (18)

1. L. Pasteur, Ann. Phys., 1848, 24, 442.
2. L. Pérez-GarcÃa and D. B. Amabilino, Chem. Soc. Rev., 2002, 31, 342.
3. J. Jacques, A. Collet and S. H. Wilen, Enantiomers, Racemates and Resolutions, John Wiley, New York, 1981.
4. Z. J. Li and D. J. W. Grant, J. Pharm. Sci., 1997, 86, 1073.
5. C. P. Brock, W. B. Schweizer and J. D. Dunitz, J. Am. Chem. Soc., 1991, 113, 9811.
6. The propensity for racemic crystal formation has led to the development of the concept of quasiracemates, crystals comprising two isosteric components that differ in handedness and chemical constitution ( M. S. Mukta, P. Hooter, R. S. Davis, V. M. Lynch and K. A. Wheeler, Cryst. Growth Des., 2004, 4, 95 ).
7. About 5â€"10% of racemic crystals assume noncentrosymmetric space groups ( B. Dalhus and C. H. Gorbitz, Acta Crystallogr., Sect. B, 2000, 56, 715 ).
8. Z. J. Li, W. H. Ojala and D. J. W. Grant, J. Pharm. Sci., 2001, 90, 1523.
9. D. P. Craig and P. E. Schipper, Chem. Phys. Lett., 1974, 25, 476.
10. K. Kinbara, Y. Hashimoto, M. Sukegawa, H. Nohira and K. Saigo, J. Am. Chem. Soc., 1996, 118, 3441.
11. S. Jayanty and T. P. Radhakrishnan, Chem. Eur. J., 2004, 10, 2661.
12. 3pez and J. Elguero, Helv. Chim. Acta, 1999, 82, 2213.
13. S. F. Alshahateet, R. Bishop, D. C. Craig and M. L. Scudder, CrystEngComm, 2002, 4, 42.
14. H. Koshima, J. Mol. Struct., 2000, 552, 111.
15. A. D. Bond, N. Feeder, J. E. Redman and J. K. M. Sanders, Acta Crystallogr., Sect. E, 2001, 57, o869.
16. P. E. Schipper and P. R. Harrowell, J. Am. Chem. Soc., 1983, 105, 723.
17. J. Rebek, Jr., T. Costello and R. Wattley, J. Am. Chem. Soc., 1985, 107, 7487.
18. SHELXTL 6.12, Bruker AXS, Inc., Madison, WI, 1997.