Halogen bond and its counterparts: Bent's rule explains the formation of nonbonding interactions

Journal of Physical Chemistry A

Volumn 115, Issue 44, 2011, Pages 12340-12347

  Grabowski, Sławomir J ^a,b  

^a UNIVERSITY OF THE BASQUE COUNTRY UPV EHU   (Spain)

^b BASQUE FOUNDATION FOR SCIENCE   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

AB INITIO CALCULATIONS; BENT'S RULE; ELECTRON CHARGE REDISTRIBUTION; HALOGEN BONDS; LEWIS ACID; LEWIS BASE; NATURAL BOND ORBITAL; NON-BONDING INTERACTIONS;

CALCULATIONS; CHLORINE; FLUORINE; HALOGEN COMPOUNDS; HYDROGEN; HYDROGEN BONDS;

COMPLEXATION;

HALOGEN;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; HYDROGEN BOND;

HALOGENS; HYDROGEN BONDING; MODELS, MOLECULAR;

EID: 80455132432     PISSN: 10895639     EISSN: 15205215     Source Type: Journal    
DOI: 10.1021/jp205019s     Document Type: Article

References (72)

1. Jeffrey, G. A. An Introduction to Hydrogen Bonding; Oxford University Press: New York, 1997.
2. Desiraju, G. R.; Steiner, T. The weak hydrogen bond in structural chemistry and biology; Oxford University Press Inc.: New York, 1999.
3. Hydrogen Bonding - New Insights; Grabowski, S. J., Eds.; Vol. 3 of the series Challenges and Advances in Computational Chemistry and Physics; Leszczynski, J., Ed.; Springer: Berlin, 2006.
4. Jeffrey, G. A.; Saenger, W. Hydrogen Bonding in Biological Structures; Springer-Verlag: Berlin, 1991.
5. Lehn, J.-M. Angew. Chem., Int. Ed. Engl. 1990, 29, 1304
6. Lehn, J.-M. Supramolecular Chemistry; Verlag-Chemie, Weinheim, 1995.
7. Hobza, P.; Müller-Dethlefs, K. Non-Covalent Interactions, Theory and Experiment; Royal Society of Chemistry: Thomas Graham House, Science Park, Milton Road, Cambridge, U.K., 2010.
8. Lipkowski, P.; Grabowski, S. J.; Leszczynski, J. J. Phys. Chem. A 2006, 110, 10296
9. Peris, E.; Lee, J. C., Jr.; Rambo, J.; Eisenstein, O.; Crabtree, R. H. J. Am. Chem. Soc. 1995, 117, 3485
10. Wessel, J.; Lee, J. C., Jr.; Peris, E.; Yap, G. P. A.; Fortin, J. B.; Ricci, J. S.; Sini, G.; Albinati, A.; Koetzle, T. F.; Eisenstein, O.; Rheingold, A. L.; Crabtree, R. H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2507
11. Crabtree, R. H.; Siegbahn, P. E. M.; Eisenstein, O.; Rheingold, A. L.; Koetzle, T. F. Acc. Chem. Res. 1996, 29, 348
12. Bakhmutow, V. I. Dihydrogen Bonds; John Wiley & Sons, Inc.: Hoboken, NJ, 2008.
13. Alkorta, I.; Rozas, I.; Elguero, J. Chem. Soc. Rev. 1998, 27, 163
14. Rozas, I.; Alkorta, I.; Elguero, J. J. Phys. Chem. A 1997, 101, 4236
15. Grabowski, S. J.; Sokalski, W. A.; Leszczynski, J. Chem. Phys. Lett. 2006, 422, 334
16. Pauling, L. The Nature of the Chemical Bond, 3rd ed.; Cornell University Press: Ithaca, NY, 1960.
17. Metrangolo, P.; Resnati, G. Chem.-Eur. J. 2001, 7, 2511
18. Zordan, F.; Brammer, L.; Sherwood, P. J. Am. Chem. Soc. 2005, 127, 5979
19. Formigué, M.; Batail, P. Chem. Rev. 2004, 104, 5379
20. Grabowski, S. J.; Leszczynski, J. Dihydrogen Bonds: Novel feature of Hydrogen Bond Interactions. In Practical Aspects of Computational Chemistry, Methods, Concepts and Applications; Leszczynki, J.; Shukla, M. K., Eds.; Springer Science+Business Media B.V.: Berlin, 2009.
21. Metrangolo, P.; Neukirch, H.; Pilati, T.; Resnati, G. Acc. Chem. Res. 2005, 38, 386
22. Clark, T.; Hennemann, M.; Murray, J. S.; Politzer, P. J. Mol. Model. 2007, 13, 291
23. Politzer, P.; Lane, P.; Concha, M. C.; Ma, Y.; Murray, J. S. J. Mol. Model. 2007, 13, 305
24. Murray, J. S.; Lane, P.; Clark, T.; Politzer, P. J. Mol. Model. 2007, 13, 1033
25. Politzer, P.; Murray, J. S.; Concha, M. C. J. Mol. Model. 2008, 14, 659
26. Murray, J.; Concha, M. C.; Lane, P.; Hobza, P.; Politzer, P. J. Mol. Model. 2008, 14, 699
27. Murray, J.; Lane, P.; Politzer, P. J. Mol. Model. 2009, 15, 723
28. Scheiner, S. J. Chem. Phys. 2011, 134, 094315
29. Scheiner, S. J. Phys. Chem. A 2011, 115, 11202
30. Alabugin, I. V.; Manoharan, M.; Peabody, S.; Weinhold, F. J. Am. Chem. Soc. 2003, 125, 5973
31. Weinhold, F.; Landis, C. Valency and Bonding, A Natural Bond Orbital Donor - Acceptor Perspective; Cambridge University Press: Cambridge, U.K., 2005.
32. Reed, A. E.; Curtiss, L. A.; Weinhold, F. Chem. Rev. 1988, 88, 899
33. Weinhold, F. J Mol. Struct. (THEOCHEM) 1997, 398-399, 181
34. Grabowski, S. J.; Ugalde, J. M. J. Phys. Chem. A 2010, 114, 7223
35. Alkorta, I.; Elguero, J.; Solimannejad, M.; Grabowski, S. J. J. Phys. Chem. A 2011, 115, 201
36. Bent, H. A. Chem. Rev. 1961, 61, 275
37. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A., Jr.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, N. J.; Klene, M.; Knox, J. E.; 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.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, Ö.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09, Revision A.1; Gaussian, Inc.: Wallingford, CT, 2009.
38. Boys, S. F.; Bernardi, F. Mol. Phys. 1970, 19, 553
39. Grabowski, S. J. Annu. Rep. Prog. Chem., Sect. C 2006, 102, 131
40. Grabowski, S. J.; Sadlej, A. J.; Sokalski, W. A.; Leszczynski, J. Chem. Phys. 2006, 327, 151
41. Glendening, E. D.; Streitwieser, A., Jr. J. Chem. Phys. 1994, 100, 2900
42. Schenter, G. K.; Glendening, E. D. J. Phys. Chem. 1996, 100, 17152
43. Glendening, E. D. J. Am. Chem. Soc. 1996, 118, 2473
44. Glendening, E. D.; Badenhoop, J; K.; Reed; A. E.; Carpenter; J. E.; Bohmann; J. A.; Morales; C. M.; Weinhold; Theoretical, F. NBO 5.0; Chemistry Institute, University of Wisconsin: Madison, 2001.
45. Schmidt, M. W.; Baldridge, K. K.; Boatz, J. A.; Elbert, S. T.; Gordon, M. S.; Jensen, J. H.; Koseki, S.; Matsunaga, N.; Nguyen, K. A.; Su, S. J.; Windus, T. L.; Dupuis, M.; Montgomery, J. A. J. Comput. Chem. 1993, 14, 1347
46. Gilli, P.; Bertolasi, V.; Ferretti, V.; Gilli, G. J. Am. Chem. Soc. 1994, 116, 909
47. Gilli, G.; Gilli, P. J. Mol. Struct. 2000, 552, 1
48. Allen, F. H.; Davies, J. E.; Galloy, J. E.; Johnson, J. J.; Kennard, O.; Macrave, C. F.; Mitchel, E. M.; Smith, J. M.; Watson, D. G. J. Chem. Inf. Comput. Sci. 1991, 31, 187
49. Cotton, F. A.; Matonic, J. H.; Murillo, C. A. J. Am. Chem. Soc. 1998, 120, 6047
50. Murray, J. S.; Riley, K. E.; Politzer, P.; Clark, T. Aust. J. Chem. 2010, 63, 1598
51. Desiraju, G. R.; Harlow, R. L. J. Am. Chem. Soc. 1989, 111, 6757
52. Auffinger, P.; Hays, F. A.; Westhof, E.; Ho, P. S. Proc. Natl. Acad. Sci. U. S. A. 2004, 101, 16789
53. Bilewicz, E.; Rybarczyk-Pirek, A. J.; Dubis, A. T.; Grabowski, S. J. J. Mol. Struct. 2007, 829, 208
54. Lommerse, J. P. M.; Stone, A. J.; Taylor, R.; Allen, F. H. J. Am. Chem. Soc. 1996, 118, 3108
55. Wang, W.; Wong, N.-B.; Zheng, W.; Tian, A. J. Phys. Chem. A 2004, 108, 1799
56. Pinchas, S. Anal. Chem. 1955, 27, 2
57. Trudeau, G.; Dumas, J. M.; Dupuis, P.; Guerin, M.; Sandorfy, C. Top. Curr. Chem. 1980, 93, 91
58. Hobza, P.; Havlas, Z. Chem. Rev. 2000, 100, 4253 and references cited therein
59. Kryachko, E. S. Neutral Blue-Shifting and Blue-Shifted Hydrogen Bonds. In Hydrogen Bonding - New Insights; Grabowski, S. J., Ed.; Springer: Dordrecht, The Netherlands, 2006; Chapter 8.
60. Palusiak, M. J. Mol. Struct. (THEOCHEM) 2010, 945, 89
61. Riley, K. E.; Hobza, P. J. Chem. Theory Comput. 2008, 4, 232
62. Morokuma, K; Kitaura, K. In Molecular Interactions; Ratajczak, H.; Orville-Thomas, W. J., Eds.; John Wiley and Sons Ltd.: New York, 1980; Vol. 1, pp 21-66.
63. Sokalski, W. A.; Roszak, S.; Pecul, K. Chem. Phys. Lett. 1988, 153, 153
64. Sokalski, W. A.; Roszak, S. J.Mol.Struct. (THEOCHEM) 1991, 234, 387
65. Corcoran, C. T.; Weinhold, F. J. Chem. Phys. 1980, 72, 2866
66. Weinhold, F.; Carpenter, J. E. J. Mol. Struct. (THEOCHEM) 1988, 165, 189
67. Jeziorski, B.; Moszynski, R.; Szalewicz, K. Chem. Rev. 1994, 94, 1887
68. Weinhold, F. Angew. Chem., Int. Ed. 2003, 42, 4188
69. Politzer, P.; Murray, J. S.; Clark, T. Phys. Chem. Chem. Phys. 2010, 12, 7748
70. Sobczyk, L.; Grabowski, S. J.; Krygowski, T. M. Chem. Rev. 2005, 105, 3513
71. Grabowski, S. J. Croat. Chem. Acta 2009, 185, 82
72. Grabowski, S. J. Chem. Rev. 2011, 11, 2597