Origin of the X-Hal (Hal = Cl, Br) bond-length change in the halogen-bonded complexes

Journal of Physical Chemistry A

Volumn 112, Issue 17, 2008, Pages 4114-4119

  Wang, Weizhou ^a   Hobza, Pavel ^a  

^a INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY   (Czech Republic)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL BONDS; COMPLEXATION; ELECTROSTATICS; HYDROGEN; HYDROGEN BONDS; NONMETALS; ORBITAL TRANSFER; ROCKETS;

AMERICAN CHEMICAL SOCIETY (ACS); ANTIBONDING ORBITAL; ATOMS-IN-MOLECULES (AIM); BLUE-SHIFTING; BOND CONTRACTION; ELECTROSTATIC POTENTIAL (ESP); FITTING METHODS; HALOGEN BONDS; NATURAL BOND ORBITAL (NBO) ANALYSIS;

BOND LENGTH;

HALOGEN; PROTON;

ARTICLE; CHEMISTRY; DIMERIZATION; HYDROGEN BOND; VIBRATION;

DIMERIZATION; HALOGENS; HYDROGEN BONDING; PROTONS; VIBRATION;

EID: 44949169876     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp710992h     Document Type: Article

References (40)

1. Jeffrey, G. A. An Introduction to Hydrogen Bonding; Oxford University Press: New York, 1997.
2. Scheiner, S. Hydrogen Bonding; Oxford University Press: New York, 1997.
3. Nishio, M.; Hirota, M.; Umezawa, Y. The CW/* Interaction: Evidence, Nature, and Consequences; Wiley-VCH: New York, 1998.
4. Desiraju, G. R.; Steiner, T. The Weak Hydrogen Bond; Oxford University Press: Oxford, 1999.
5. It must be pointed out that the definition of the hydrogen bond is still being debated. See, for example, Arunan, E.; Klein, R. A. IUPAC Workshop, "Hydrogen Bonding and Other Molecular Interactions", Pisa, Italy, Sept 5-9, 2005 and Bangalore, India, Sept 18-22, 2006; http://ipc.iisc.ernet.in/
6. Guthrie, F. J. Chem. Soc. 1863, 16, 239.
7. Metrangolo, P.; Resnati, G. Chem.-Eur. J. 2001, 7, 2511, and references therein.
8. Metrangolo, P.; Neukirch, H.; Pilati, T.; Resnati, G. Acc. Chem. Res. 2005, 38, 386, and references therein.
9. Metrangolo, P.; Resnati, G.; Pilati, T.; Liantonio, R.; Meyer, F. J. Polym. Sci., Part A: Polym. Chem. 2007, 45, 1, and references therein.
10. Auffinger, P.; Hays, F. A.; Westhof, E.; Ho, P. S. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 16789.
11. Politzer, P.; Lane, P.; Concha, M. C.; Ma, Y. G.; Murray, J. S. J. Mol. Model. 2007, 13, 305.
12. Clark, T.; Hennemann, M.; Murray, J. S.; Politzer, P. J. Mol. Model. 2007, 13, 291.
13. Lommerse, J. P. M.; Stone, A. J.; Taylor, R.; Allen, F. H. J. Am. Chem. Soc. 1996, 118, 3108.
14. Riley, K. E.; Hobza, P. J. Theor. Comput. Chem. 2008, 4, 232.
15. Metrangolo, P.; Piláti, T.; Resnati, G. Cryst. Eng. Commun. 2006, 5, 946.
16. Wang, W. Z.; Wong, N. B.; Zheng, W. X.; Tian, A. M. J. Phys. Chem. A 2004, 108, 1799.
17. 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.
18. Wang, W. Z.; Tian, A. M.; Wong, N. B. J. Phys. Chem. A 2005, 109, 8035.
19. Riley, K. E.; Merz, K. M. J. Phys. Chem. A 2007, 111, 1688.
20. Lu, Y. X.; Zou, J. W.; Wang, Y. H.; Jiang, Y. J.; Yu, Q. S. J. Phys. Chem. A 2007, 111, 10781.
21. Valerio, G.; Raos, G.; Meule, S. V.; Metrangolo, P.; Resnati, G. J. Phys. Chem. A 2000, 104, 1617.
22. Farina, A.; Meille, S. V.; Messina, M. T.; Metrangolo, P.; Resnati, G.; Vecchio, G. Angew. Chem., Int. Ed. Engl. 1999, 38, 2433.
23. Liantonio, R.; Luzzati, S.; Metrangolo, P.; Pilati, T.; Resnati, G. Tetrahedron 2002, 58, 4023.
24. Fox, D. B.; Liantonio, R.; Metrangolo, P.; Pilati, T.; Resnati, G. J. Fluorine Chem. 2004, 125, 271.
25. Metrangolo, P.; Resnati, G.; Pilati, T.; Biella, S. Halogen Bonding in Crystal Engineering. In Halogen Bonding: Fundamentals and Applications; Metrangolo, P., Resnati, G., Eds.; Springer: Berlin/Heidelberg, 2008, pp 105-136.
26. Hobza, P.; Spirko, V.; Selzle, H. L.; Schlag, E. W. J. Phys. Chem. A 1998, 102, 2501.
27. Hobza, P.; Havlas, Z. Chem. Rev. 2000, 100, 4253.
28. At the MP2/SDD theory level.
29. Hobza, P.; Havlas, Z. Chem. Phys. Lett. 1999, 303, 447.
30. Hermansson, K. J. Phys. Chem. A 2002, 106, 4695.
31. Li, X.; Liu, L.; Schlegel, H. B. J. Am. Chem. Soc. 2002, 124, 9639.
32. Alabugin, I. V.; Manoharan, M.; Peabody, S.; Weinhold, F. J. Am. Chem. Soc. 2003, 125, 5973.
33. Joseph, J.; Jemmis, E. D. J. Am. Chem. Soc. 2007, 129, 4620.
34. McDowell, S. A. C.; Buckingham, A. D. J. Am. Chem. Soc. 2005, 127, 15515.
35. Lu, P.; Liu, G.; Li, J. J. Mol. Struct. (THEOCHEM) 2005, 723, 95.
36. Boys, S. F.; Bernardi, F. Mol. Phys. 1970, 19, 553.
37. Reed, A. E.; Curtiss, L. A.; Weinhold, F. Chem. Rev. 1988, 88, 889.
38. Breneman, C. M.; Wiberg, K. B. J. Comput. Chem. 1990, 11, 361.
39. Bader, R. W. F. Atoms in Molecules. A Quantum Theory; Oxford University Press: Oxford, 1990.
40. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; 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.; Pople, J. A. Gaussian 03, revision C.02; Gaussian: Wallingford, CT, 2004.