Crystal and molecular structure of pyrrole-2-carboxylic acid; π-electron delocalization of its dimers-DFT and MP2 calculations

Journal of Physical Chemistry A

Volumn 108, Issue 27, 2004, Pages 5815-5822

  Grabowski, Sławomir J ^a,b   Dubis, Alina T ^c   Martynowski, Dariusz ^d   Główka, Marek ^d   Palusiak, Marcin ^a   Leszczynski, Jerzy ^b  

^a UNIVERSITY OF LODZ   (Poland)

^b JACKSON STATE UNIVERSITY   (United States)

^c UNIVERSITY OF BIALYSTOK   (Poland)

^d LODZ UNIVERSITY OF TECHNOLOGY   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

DELOCALIZATION; PYRROLE MOIETY;

CRYSTALS; DATA REDUCTION; ELECTRONS; HYDROGEN BONDS; MOLECULAR STRUCTURE; X RAY DIFFRACTION ANALYSIS;

CARBOXYLIC ACIDS;

EID: 3142772679     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp0373595     Document Type: Article

References (50)

1. Jeffrey, G. A.; Saenger, W. Hydrogen Bonding in Biological Structures; Springer-Verlag: Berlin, 1991.
2. Allen, F. H.; Motherwell, W. D. S.; Raithby, P. R.; Shields, G. P.; Taylor, R. New J. Chem. 1999, 23, 25.
3. Desiraju, G. R. Crystal Engineering - The Design of Organic Solids; Elsevier: Amsterdam, 1989.
4. Jeffrey, G. A. An Introduction to Hydrogen Bonding; Oxford University Press: New York, 1997.
5. Desiraju, G. R.; Steiner, T. The Weak Hydrogen Bond in Structural Chemistry and Biology; Oxford University Press, Inc.: New York, 1999.
6. Rybarczyk-Pirek, A. J.; Grabowski, S. J.; Małecka, M.; Nawrot-Modranka, J. J. Phys. Chem. A 2002, 106, 11956.
7. (a) Gilli, G.; Bellucci, F.; Ferretti, V.; Bertolasi, V. J. Am. Chem. Soc. 1989, 111, 1023.
8. (b) Bertolasi, V.; Gilli, P.; Ferretti, V.; Gilli, G. J. Am. Chem. Soc. 1991, 113, 4917.
9. (c) Gilli, P.; Bertolasi, V.; Ferretti, V.; Gilli, G. J. Am. Chem. Soc. 1994, 116, 909.
10. (d) Gilli, P.; Bertolasi, V.; Ferretti, V.; Gilli, G. J. Am. Chem. Soc. 2000, 122, 10405.
11. (e) Gilli, P.; Bertolasi, V.; Pretto, L.; Lyčka, A.; Gilli, G. J. Am. Chem. Soc. 2002, 124, 13554.
12. (f) Gilli, P.; Bertolasi, V.; Pretto, L.; Ferretti, V.; Gilli, G. J. Am. Chem. Soc. 2004, 126, 3845.
13. Madsen, G. K. H.; Iversen, B. B.; Larsen, F. K.; Kapon, M.; Reisner, G. M.; Herbstein, F. H. J. Am. Chem. Soc. 1998, 120, 10040.
14. Wojtulewski, S.; Grabowski, S. J. Chem. Phys. Lett. 2003, 378, 388.
15. Grabowski, S. J. J. Mol. Struct. 2001, 562, 137.
16. (a) González, L.; Mó, O.; Yáñez, M. J. Org. Chem. 1999, 64, 2314.
17. (b) Sanz, P.; Yáñez, M.; Mó, O. J. Phys. Chem. A 2002, 106, 4661.
18. Rybarczyk, A. J.; Małecka, M.; Grabowski, S. J.; Nawrot-Modranka, J. Acta Crystallogr., Sect. C 2002, 55, 405.
19. Bertolasi, V.; Gilli, P.; Ferretti, V.; Gilli, G. Acta Crystallogr., Sect. B 1995, 51, 1004.
20. Dubis, A.; Grabowski, S. J.; Romanowska, D. B.; Misiaszek, T.; Leszczynski, J. J. Phys. Chem. A 2002, 106, 10613.
21. Bader, R. F. W. Atoms in Molecules. A Quantum Theory; Oxford University Press: New York, 1990.
22. Anderson, H. J.; Hopkins, L. C. Can. J. Chem. 1964, 42, 1279.
23. Sheldrick, G. M. SHELXS, Program for Crystal Structure Solution; University of Göttingen: Germany, 1997.
24. Sheldrick G. M. SHELXL, Program for Refinement of Crystal Structures; University of Göttingen: Germany, 1997.
25. Nardelli, M. J. Appl. Crystallogr. 1996, 29, 296.
26. Spek, A. L. PLATON, Molecular Geometry Program; University of Utrecht: The Netherlands, 1998.
27. Cambridge Structural Database System; Cambridge Crystallographic Data Centre: Cambridge, U.K., 2003.
28. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, L. R.; Fox, D. J.; Keith, T.; Al.-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, G.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.: Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, revision A.6; Gaussian, Inc.: Pittsburgh, PA, 1998.
29. Boys, S. F.; Bernardi, F. Mol. Phys. 1970, 19, 553.
30. Carrol, M. T.; Chang, C.; Bader, R. F. W. Mol. Phys. 1988, 63, 387.
31. Carrol, M. T.; Bader, R. F. W. Mol. Phys. 1988, 65, 695.
32. AIM2000 designed by Friedrich Biegler-König, University of Applied Sciences, Bielefeld, Germany.
33. Jeffrey, G. A.; Lewis, L. Carbohydr. Res. 1978, 60, 179.
34. Taylor, R.; Kennard, O. Acta Crystallogr. 1983, B39, 133.
35. Leiserowitz, L. Acta Crystallogr., Sect. B 1976, 32, 775.
36. Bernstein, J.; Etter, M. C.; Leiserowitz, L. The Role of Hydrogen Bonding in Molecular Assemblies. In Structure Correlation; Bürgi, H.-B., Dunitz, J. D., Eds.; VCH: Weinheim, 1994.
37. Etter, M. C. Acc. Chem. Res. 1990, 23, 120.
38. Taylor, R.; Kennard, O. J. Am. Chem. Soc. 1982, 104, 5063.
39. Grabowski, S. J. Monatsh. Chem. 2002, 133, 1373.
40. Chojnacki, H.; Andzelm, J. W.; Nguyen, D. T.; Sokalski, W. A. Comput. Chem. 1995, 19, 181.
41. Kim, Y. J. Am. Chem. Soc. 1996, 118, 1522.
42. Miura, S.; Tuckerman, M. E.: Klein, M. L. J. Chem. Phys. 1998, 109, 5290.
43. Ushiyama, H.; Takatsuka, K. J. Chem. Phys. 2001, 115, 5903.
44. Grabowski, S. J.; Krygowski, T. M. Chem. Phys. Lett. 1988, 151, 425.
45. Grabowski, S. J.; Krygowski, T. M. Chem. Phys. Lett. 1999, 305, 247.
46. (a) Alkorta, I.; Rozas, I.; Elguero, J. Struct. Chem. 1998, 9, 243.
47. (b) Alkorta, I.; Barrios, L.; Rozas, I.; Elguero, J. J. Mol. Struct (THEOCHEM) 2000, 496,131.
48. (c) Alkorta, I.; Elguero, J.; Mó, O.; Yánez, M.; Del Bene, J. E. J. Phys. Chem. A 2002, 106, 9325.
49. (d) Pacios, L. F. J. Phys. Chem. A 2004, 108, 1177.
50. Rybarczyk-Pirek, A. J.; Grabowski, S. J.; Nawrot-Modranka, J. J. Phys. Chem. A 2003, 107, 9232.