Experimental and theoretical study of the Br⋯N halogen bond in complexes of 1,4-dibromotetrafluorobenzene with dipyridyl derivatives

Journal of Physical Chemistry A

Volumn 113, Issue 14, 2009, Pages 3403-3412

  Forni, Alessandra ^a  

^a CNR   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

DFT CALCULATIONS; ELECTRON DENSITY DISTRIBUTIONS; GAS-PHASE; HALOGEN BONDINGS; HALOGEN BONDS; HALOGEN SPECIES; INFINITE CHAINS; PYRIDYL; QUANTITATIVE EVALUATIONS; QUANTUM THEORY OF ATOMS IN MOLECULES; THEORETICAL DENSITIES; THEORETICAL STUDIES; TOPOLOGICAL FEATURES;

ETHYLENE; QUANTUM THEORY; SULFUR COMPOUNDS;

HALOGEN COMPOUNDS;

1,4 DIBROMOTETRAFLUOROBENZENE; 1,4-DIBROMOTETRAFLUOROBENZENE; 2,2' BIPYRIDINE; BROMINE; FLUOROBENZENE; NITROGEN;

ARTICLE; CHEMISTRY; ELECTRON; QUANTUM THEORY; X RAY CRYSTALLOGRAPHY;

2,2'-DIPYRIDYL; BROMINE; CRYSTALLOGRAPHY, X-RAY; ELECTRONS; FLUOROBENZENES; NITROGEN; QUANTUM THEORY;

EID: 64849114736     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp8107182     Document Type: Article

References (64)

1. Metrangolo, P., Resnati, G., Eds.; Halogen Bonding: Fundamentals and Applications; Springer: Berlin, 2008, and references therein.
2. (a) Desiraju, G. R.; Harlow, R. L. J. Am. Chem. Soc. 1989, 111, 6757-6764.
3. (b) Bailey, R. D.; Grabarczyk, M.; Hanks, T. W.; Pennington, W. T. J. Chem. Soc., Perkin Trans. 1997, 2, 2781-2786.
4. (c) Metrangolo, P.; Neukirch, H.; Pilati, T.; Resnati, G. Acc. Chem. Res. 2005, 38, 386- 395.
5. (d) Metrangolo, P.; Meyer, F.; Pilati, T.; Resnati, G.; Terraneo, G. Angew. Chem., Int. Ed. 2008, 47, 6114-6127.
6. (a) Fourmigué, M.; Batail, P. Chem. Rev. 2004, 104, 5379-5418.
7. (b) Shirahata, T.; Kibune, M.; Maesato, M.; Kawashima, T.; Saito, G.; Imakubo, T. J. Mater. Chem. 2006, 16, 3381-3390.
8. (c) Metrangolo, P.; Präsang, C.; Resnati, G.; Liantonio, R.; Whitwood, A. C.; Bruce, D. W. Chem. Commun. 2006, 3290-3292.
9. (d) Xu, J.; Liu, X.; Kok-Peng Ng, J.; Lin, T.; He, C. J. Mater. Chem. 2006, 16, 3540-3545.
10. (e) Sarma, J. A. R. P.; Allen, F. H.; Hoy, V. J.; Howard, J. A. K.; Thaimattam, R.; Biradha, K.; Desiraju, G. R. Chem. Commun. 1997, 101-102.
11. (f) Thallapally, P. K.; Desiraju, G. R.; Bagieu-Beucher, M.; Masse, R.; Bourgogne, C.; Nicoud, J. F. Chem. Commun. 2002, 1052-1053.
12. (g) Cariati, E.; Forni, A.; Biella, S.; Metrangolo, P.; Meyer, F.; Resnati, G.; Righetto, S.; Tordin, E.; Ugo, R. Chem. Commun. 2007, 2590-2592.
13. (h) Kamal Boubekeur, K.; Syssa-Magalé, J.-L.; Palvadeau, P.; Schöllhorn, B. Tetrahedron Lett. 2006, 47, 1249-1252.
14. Auffinger, P.; Hays, F. A.; Westhof, E.; Ho, P. S. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 16789-16794.
15. Wojtczak, A.; Cody, V.; Luft, J. R.; Pangborn, W. Acta Crystallogr., Sect. D 2001, 57, 1061-1070.
16. (a) Howard, E. I.; Sanishvili, R.; Cachau, R. E.; Mitschler, A.; Chevrier, B.; Barth, P.; Lamour, V.; Van Zandt, M.; Sibley, E.; Bon, C.; Moras, D.; Schneider, T. R.; Joachimiak, A.; Podjarny, A. Proteins 2004, 55, 792-804.
17. (b) Muzet, N.; Guillot, B.; Jelsch, C.; Howard, E.; Lecomte, C. Proc. Natl. Acad. Sci. U.S.A. 2003, 100, 8742-8747.
18. (a) Hassel, O.; Hvoslef, J. Acta Chem. Scand. 1954, 8, 1953.
19. (b) Hassel, O. Mol. Phys. 1958, 241-246.
20. (c) Hassel, O. Science 1970, 170, 497-502.
21. (d) Bent, H. A. Chem. Rev. 1968, 68, 587-648.
22. Metrangolo, P.; Resnati, G. Chem. Eur. J. 2001, 7, 2511-2519.
23. (a) De Santis, A.; Forni, A.; Liantonio, R.; Metrangolo, P.; Pilati, T.; Resnati, G. Chem. Eur. J. 2003, 9, 3974-3983.
24. (b) Forni, A.; Metrangolo, P.; Pilati, T.; Resnati, G. Cryst. Growth Des. 2004, 4, 291-295.
25. (c) Walsh, R. B.; Padgett, C. W.; Metrangolo, P.; Resnati, G.; Hanks, T. W.; Pennington, W. T. Cryst. Growth Des. 2001, 1, 165-175.
26. (d) Corradi, E.; Meille, S. V.; Messina, M. T.; Metrangolo, P.; Resnati, G. Angew. Chem., Int. Ed. 2000, 39, 1782-1786.
27. Lommerse, J. P. M.; Stone, A. J.; Taylor, R.; Allen, F. H. J. Am. Chem. Soc. 1996, 118, 3108-3116.
28. (a) Brinck, T.; Murray, J. S.; Politzer, P. Int. J. Quantum Chem. Quantum Biol. Symp. 1992, 44, 57-64.
29. (b) Politzer, P.; Lane, P.; Concha, M. C.; Ma, Y.; Murray, J. S. J. Mol. Model. 2007, 13, 305-311.
30. (a) Clark, T.; Hennemann, H.; Murray, J. S.; Politzer, P. J. Mol. Model. 2007, 13, 291-296.
31. (b) Politzer, P.; Murray, J. S.; Lane, P. Int. J. Quantum Chem. 2007, 107, 3046-3052.
32. (c) Murray, J. S.; Concha, M. C.; Lane, P.; Hobza, P.; Politzer, P. J. Mol. Model. 2008, 14, 699-704.
33. Wang, W. Z.; Wong, N. B.; Zheng, W. X.; Tian, A. M. J. Phys. Chem. A 2004, 108, 1799-1805.
34. Zou, J. W.; Jiang, Y. J.; Guo, M.; Hu, G. X.; Zhang, B.; Liu, H. C.; Yu, Q. S. Chem. Eur. J. 2005, 11, 740-751.
35. Wang, W.; Hobza, P. J. Phys. Chem. A 2008, 112, 4114-4119.
36. Hermansson, K. J. Phys. Chem. A 2002, 106, 4695-4702.
37. Qian, W.; Krimm, S. J. Phys. Chem. A 2002, 106, 6628-6636.
38. Bianchi, R.; Forni, A.; Pilati, T. Chem. Eur. J. 2003, 9, 1631-1638.
39. Bianchi, R.; Forni, A.; Pilati, T. Acta Crystallogr. Sect. B 2004, 60, 559-568.
40. Stewart, R. Acta Crystallogr., Sect. A 1976, 32, 565-574.
41. Bianchi, R.; Forni, A. J. Appl. Crystallogr. 2005, 38, 232-236.
42. Clementi, E.; Roetti, C. At. Data Nucl. Data Tables 1974, 14, 177-478.
43. (a) Hehre, W. J.; Ditchfield, R.; Stewart, R. F.; Pople, J. A. J. Chem. Phys. 1970, 52, 2769-2773.
44. (b) Pietro, W. J.; Levi, B. A.; Hehre, W. J.; Stewart, R. F. Inorg. Chem. 1980, 19, 2225-2229.
45. 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.; Bakken, V.; 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.; Pople, J. A. Gaussian 03, Revision D.01; Gaussian Inc.: Pittsburgh, PA, 2003.
46. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789.
47. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.
48. Boys, S. F.; Bernardi, F. Mol. Phys. 1970, 19, 553-566.
49. Bader, R. F. W. AIMPAC: A set of programs for the theory of atoms in molecules; McMaster University: Hamilton, Ontario, Canada L8S 4M1, 1994.
50. Saunders, V. R.; Dovesi, R.; Roetti, C.; Causà M., Harrison, N. M.; Orlando, R.; Zicovich-Wilson, C. M. CRYSTAL98 User'S Manual; University of Torino, Torino, Italy, 1998.
51. Gatti, C. TOPOND-98: an electron density topological program for systems periodic in N (N = 0-3) dimensions, User's Manual; CNRCSRSRC, Milan, Italy;http://www.istm.cnr.it/~gatti/TOPOND.ppt, 1999.
52. Bader, R. F. W. Atoms in Molecules-A Quantum Theory; Oxford University Press: Oxford, UK, 1994.
53. Bondi, A. J. Phys. Chem. 1964, 68, 441-451.
54. Note that the different appearance of the contour levels around bromine in parts a and b of Figure 5 is due to the noncoplanarity of the two molecular modules. The two parts are in fact plotted in different molecular planes.
55. Bader, R. F. W.; Beddall, P. M. J. Chem. Phys. 1972, 56, 3320-3329.
56. Abramov, Yu. A. Acta Crystallogr., Sect. A 1997, 53, 264-272.
57. Espinosa, E.; Molins, E.; Lecomte, C. Chem. Phys. Lett. 1998, 285, 170-173.
58. Espinosa, E.; Alkorta, I.; Elguero, J.; Molins, E. J. Chem. Phys. 2002, 117, 5529-5542.
59. Koritsanszky, T. S.; Coppens, P. Chem. Rev. 2001, 101, 1583-1627.
60. Matta, C. F.; Hernandez-Trujillo, J.; Tang, T.-H.; Bader, R. F. W. Chem. Eur. J. 2003, 9, 1940-1951.
61. Hibbs, D. E.; Overgaard, J.; Platts, J. A.; Waller, M. P.; Hursthouse, M. B. J. Phys. Chem. B 2004, 108, 3663-3672.
62. The values of molecular charge reported here and in Table 8 refer in all cases to full molecules, but integration of course has been done on only the independent half molecule.
63. Note that there is not an equal and opposite charge on dimer B, which in fact lacks 1.04(2) e (0.52(2) e on the asymmetric unit), owing to the error connected to the integration procedure (see section 2 (Methods: Evaluation of Atomic Charges).
64. 2 to the other one prompted us to perform further multipole refinements of this structure where the core and the spherical valence populations of each atom of a dimer were constrained to be equal to those of the corresponding atoms of the other dimer of the asymmetric unit. This refinement did not imply any significant variation in the topological properties at BCPs and, obviously, no charge transfer between dimers has been obtained. In this case, charge transfer within each dimer was virtually zero.