Classification of hydrogen-bond motives in crystals of NH-pyrazoles: A mixed empirical and theoretical approach

Arkivoc

Volumn 2006, Issue 2, 2006, Pages 15-30

  Alkorta, Ibon ^a   Elguero, José ^a   Foces Foces, Concepción ^b   Infantes, Lourdes ^b  

^a INSTITUTO DE QUÍMICA MÉDICA   (Spain)

^b INSTITUTO DE QUÍMICA FÍSICA ROCASOLANO   (Spain)

Author keywords

Cambridge Structural Database; Crystal structures; DFT calculations; Hydrogen bonds; Molar refractivity; Pyrazoles

Indexed keywords

EID: 27844608985     PISSN: 14246376     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (19)

1. Cammers, A.; Parkin, S. Cryst. Eng. Comm. 2004, 6, 168.
2. (a) Etter, M. C. Acc. Chem. Res. 1990, 23, 120.
3. (b) Etter, M. C.; MacDonald, J.; Bernstein, J. Acta Crystallogr. Sect. B 1990, B46, 256.
4. (a) Bernstein, J.; Etter, M. C.; Leiserowitz, L. "The Role of Hydrogen Bonding in Molecular Assemblies" In Structure Correlations; Dunitz, J. D.; Burgi, H.-B. Eds. Vol. 2, VCH: Weinheim, 1994, pp 431-507.
5. (b) Bernstein, J.; Davis, R. E.; Shimoni, L. Chang, N.-L. Angew. Chem, Int. Ed. 1995, 34, 1555.
6. Foces-Foces, C.; Alkorta, I.; Elguero, J. Acta Crystallogr. Sect. B 2000, B56, 1018.
7. Hansch, C.; Leo, A.; Hoekman, D. Exploring QSAR. Hydrophobic, Electronic, and Steric Constants, American Chemical Society, Washington, 1995.
8. (a) Infantes, L.; Motherwell, S. Struct. Chem. 2004, 15, 173.
9. (b) Infantes, L.; Motherwell, S. Chem. Commun. 2004, 1166.
10. Fayos, J.; Infantes, L.; Cano, F. H. Cryst. Growth Design 2005, 5, 191.
11. (a) Becke, A. D. Phys. Rev. A 1988, 38, 3098.
12. (b) Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
13. (c) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
14. Hariharan, P. A.; Pople, J. A. Theor. Chim. Acta 1973, 28, 213.
15. Gaussian 03, Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, Jr., J. A.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C. and Pople, J. A. Gaussian, Inc., Pittsburgh PA, 2003.
16. RPluto, A program for crystal structure visualization, Cambridge Crystallographic Data Centre, Cambridge, 2002 (http://www.ccdc.cam.ac.uk, freely downloadable for noncommercial use).
17. (a) Elguero, J.; Marzin, C.; Katritzky, A. R.; Linda, P. The Tautomerism of Heterocycles, Academic Press: New York, 1976.
18. (b) Minkin, V. I.; Garnovskii, A. D.; Elguero, J.; Katritzky, A. R.; Denisko, O. V. Adv. Heterocycl. Chem. 2000, 76, 157.
19. Allen, F. H. Acta Crystallogr. Sect. B 2002, 58, 380.