Hydrogen bonding and electron donor-acceptor (EDA) interactions controlling the crystal packing of picric acid and its adducts with nitrogen bases. Their rationalization in terms of the p K a equalization and electron-pair saturation concepts

Crystal Growth and Design

Volumn 11, Issue 7, 2011, Pages 2724-2735

  Bertolasi, Valerio ^a   Gilli, Paola ^a   Gilli, Gastone ^a  

^a UNIVERSITY OF FERRARA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

CLOSED SHELLS; CRYSTAL PACKINGS; ELECTRON ACCEPTOR; ELECTRON DONOR ACCEPTORS; ELECTRON DONORS; ELECTRON-PAIR; H-BONDS; INTERACTION STRENGTH; INTERMOLECULAR CONTACTS; LONE PAIR; MULTIPLE BONDS; NITROGEN BASIS; PICRIC ACID; VAN DER WAALS RADIUS;

HYDROGEN BONDS; VAN DER WAALS FORCES; X RAY DIFFRACTION;

ELECTRONS;

EID: 79960055703     PISSN: 15287483     EISSN: 15287505     Source Type: Journal    
DOI: 10.1021/cg101007a     Document Type: Article

References (67)

1. Kitaigorodsky, A. I. Molecular Crystals and Molecules; Academic Press: New York, 1973.
2. Jeffrey, G. A. An Introduction to Hydrogen Bonding; Oxford University Press: Oxford, 1997.
3. Desiraju, G. R.; Steiner, Th. The Weak Hydrogen Bond in Structural Chemistry and Biology; Oxford University Press: Oxford, 1999.
4. Gilli, G.; Gilli, P. The Nature of the Hydrogen Bond. Outline of a Comprehensive Hydrogen Bond Theory; Oxford University Press: Oxford, 2009.
5. Gilli, P.; Pretto, L.; Gilli, G. J. Mol. Struct. 2007, 844-845, 328-339
6. Gilli, P.; Pretto, L.; Bertolasi, V.; Gilli, G. Acc. Chem. Res. 2009, 42, 33-44
7. Gilli, P.; Gilli, G. J. Mol. Struct. 2010, 972, 2-10
8. Taylor, R.; Kennard, O. J. Am. Chem. Soc. 1982, 104, 5063-5070
9. Mulliken, R. S. J. Phys. Chem. 1952, 56, 801-822
10. Mulliken, R. S.; Person, W. B. Molecular Complexes: A Lecture and Reprint Volume; Wiley-Interscience: New York, 1969.
11. Herbstein, F. H. Crystalline Molecular Complexes and Compounds; Oxford University Press: Oxford, 2005.
12. Rosokha, S. V.; Kochi, J. K. Acc. Chem. Res. 2008, 41, 641-653
13. Gilli, G.; Gilli, P. Molecules and Molecular Crystals. In Fundamentals of Crystallography, 3 rd ed.; Giacovazzo, C. Ed.; Oxford University Press: Oxford, 2011; Chapter 8.
14. Dumas, J.-M.; Peurichard, H.; Gomel, M. J. Chem. Res. 1978, (S), 54-57
15. Legon, A. C. Angew. Chem., Int. Ed. 1999, 38, 2686-2714
16. Metrangolo, P.; Resnati, G. Chem.Eur.J. 2001, 7, 2511-2519
17. Auffinger, P.; Hays, F. A.; Weshtof, E.; Ho, P. S. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 16789-16794
18. Metrangolo, P.; Neukirch, H.; Pilati, T.; Resnati, G. Acc. Chem. Res. 2005, 38, 386-395
19. Ratajczak, H.; Orville-Thomas, W. J., Eds.; Molecular Interactions; John Wiley & Sons: Chichester, 1980; Vol. 1, p 15.
20. Donahue, J. J. Phys. Chem. 1952, 56, 502-510
21. Etter, M. C. J. Phys. Chem. 1991, 95, 4601-4610
22. Bertolasi, V.; Gilli, P.; Ferretti, V.; Gilli, G. Acta Crystallogr. 2001, B57, 591-598
23. Bertolasi, V.; Pretto, L; Gilli, P.; Ferretti, V.; Gilli, G. New J. Chem. 2002, 26, 1559-1566
24. Gilli, G.; Bertolasi, V.; Gilli, P.; Ferretti, V. Acta Crystallogr. 2001, B57, 859-865
25. Otwinowski, Z.; Minor, W. Methods Enzymol. 1997, 276, 307-326
26. Duesler, E. N.; Engelmann, J. H.; Curtin, D. Y.; Paul, I. C. Cryst. Struct. Commun. 1978, 7, 449-453
27. Srikrishnan, P.; Soriano-Garcia, M.; Parthasarathy, R. Z. Kristallogr. 1980, 151, 317-323
28. Altomare, A.; Burla, M. C.; Camalli, M.; Cascarano, G. L.; Giacovazzo, C.; Guagliardi, A.; Moliterni, A. G.; Polidori, G.; Spagna, R. SIR97. J. Appl. Crystallogr. 1999, 32, 115 - 119.
29. Sheldrick, G. M. SHELX-97, Program for Crystal Structure Refinement; University of Göttingen: Germany, 1997.
30. Nardelli, M. J. Appl. Crystallogr. 1995, 28, 659
31. Spek, A. L. PLATON, A Multipurpose Crystallographic Tool; Utrecht University: The Netherlands, 2002.
32. Farrugia, L. J. J. Appl. Crystallogr. 1999, 32, 837
33. Burnett, M. N.; Johnson, C. K. ORTEP III, Report ORNL-6895; Oak Ridge National Laboratory: Oak Ridge, TN, 1996.
34. Bondi, A. J. Phys. Chem. 1964, 68, 441-451
35. Lippincott, E. R.; Schroeder, R. J. Chem. Phys. 1955, 23, 1099-1106
36. Schroeder, R.; Lippincott, E. R. J. Phys. Chem. 1957, 61, 921-928
37. Gilli, P.; Gilli, G. LSHB. A Computer Program for Performing Lippincott and Schroeder HB Calculations; University of Ferrara: Italy, 1992.
38. Bock, H.; Dienelt, R.; Schödel, H.; Havlas, Z. J. Chem. Soc. Chem. Commun. 1993, 1792-1793
39. Artali, R.; Bombieri, G.; Carvalho, C. Z. Kristallogr. 2002, 217, 88-90
40. Zukerman-Schpector, J.; Vega-Telijido, M.; Carvalho, C. C.; Isolani, P. C.; Caracelli, I. Z. Kristallogr. 2007, 222, 427-431
41. Llamas-Saiz, A. L.; Foces-Foces, C.; Echevarría, A.; Elguero, J. Acta Crystallogr. 1995, C51, 1401-1404
42. Steiner, Th.; Majerz, I.; Wilson, C. C. Angew. Chem., Int. Ed. 2001, 40, 2651-2654
43. Majerz, I.; Sawka-Dobrowolska, W.; Sobczyk, L. J. Mol. Struct. 1993, 297, 177-184
44. Huyskens, P.; Sobczyk, L.; Majerz, I. J. Mol. Struct. 2002, 615, 61-72
45. Ratajczak, H.; Sobczyk, L. J. Chem. Phys. 1969, 50, 556-557
46. Malarski, Z.; Rospenk, M.; Sobczyk, L.; Grech, E. J. Phys. Chem. 1982, 86, 401-406
47. Majerz, I.; Malarski, Z.; Sobczyk, L. Chem. Phys. Lett. 1997, 274, 361-364
48. Sobczyk, L. Ber. Bunsenges. Phys. Chem. 1998, 102, 377-383
49. Brycki, B.; Szafran, M. J. Chem. Soc. Perkin Trans. II 1982, 1333-1338
50. Dega-Szafran, Z.; Dulewicz, E. J. Chem. Soc. Perkin Trans. II 1983, 345-351
51. Dega-Szafran, Z.; Katrusiak, A.; Szafran, M.; Tykarska, E. J. Mol. Struct. 1999, 484, 49-61
52. Arey, J. S.; Aeberhard, P. C.; Lin, I.-C.; Rothlisberger, U. J. Phys. Chem. 2009, B113, 4726-4732
53. Day, G. M.; Cooper, T. G.; Cruz-Cabeza, A. J. Acta Crystallogr. 2009, B65, 107-125
54. Neumann, M. A.; Leusen, F. J. J.; Kendrick, J. Angew. Chem., Int. Ed. 2008, 47, 2427-2430
55. London, F. Z. Phys. Chem. 1930, B11, 222-251
56. London, F. Z. Phys. 1930, 63, 245-279
57. Kresse, G.; Joubert, D. Phys. Rev. 1999, B59, 1758-1775
58. Neumann, M. A.; Perrin, M. A. J. Phys. Chem. 2005, B109, 15531-15541
59. Politzer, P.; Truhlar, D. G., Eds.; Chemical Applications of Atomic and Molecular Electrostatic Potentials; Plenum Press: New York, 1981.
60. Coppens, P.; Hall, M. B., Eds.; Electron Distributions and the Chemical Bond; Plenum Press: New York, 1982.
61. Coppens, P. X-Ray Charge Densities and Chemical Bonding; Oxford University Press: New York, 1997.
62. Koritsanszky, T. S.; Coppens, P. Chem. Rev. 2001, 101, 1583-1627
63. Bader, R. F. W. Atoms in Molecules: A Quantum Theory; Oxford University Press: Oxford, 1990.
64. Bader, R. F. W.; Gatti, C. Chem. Phys. Lett. 1998, 287, 233-238
65. Gatti, C.; Cargnoni, F.; Bertini, L. J. Comput. Chem. 2003, 24, 422-436
66. Becke, A. D.; Edgecombe, K. E. J. Chem. Phys. 1990, 92, 5397-5403
67. Fuster, F.; Silvi, B. Theor. Chem. Acc. 2000, 104, 13-21