The C-H···Cl hydrogen bond: Does it exist?

New Journal of Chemistry

Volumn 23, Issue 2, 1999, Pages 145-152

  Aakeröy, Christer B ^a   Evans, Timothy A ^b   Seddon, Kenneth R ^b   Pálinkó, István ^c  

^a KANSAS STATE UNIVERSITY   (United States)

^b QUEEN'S UNIVERSITY BELFAST   (United Kingdom)

^c UNIVERSITY OF SZEGED   (Hungary)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; CHLORIDE ION; HALIDE; HYDROGEN;

ARTICLE; CHEMICAL BOND; CONTROLLED STUDY; HYDROGEN BOND; MOLECULAR INTERACTION; PRIORITY JOURNAL;

EID: 0032766231     PISSN: 11440546     EISSN: None     Source Type: Journal    
DOI: 10.1039/a809309a     Document Type: Article

References (42)

1. S. Glasstone, Trans. Faraday Soc., 1937, 33, 200.
2. J. Donohue, in Structural Chemistry and Molecular Biology, ed. A. Rich and N. Davidson, W. H. Freeman, San Francisco, CA, 1968.
3. R. Taylor and O. Kennard, J. Am. Chem. Soc., 1982, 104, 5063.
4. D. Braga, F. Grepioni, K. Biradha, V. R. Pedireddi and G. R. Desiraju, J. Am. Chem. Soc., 1995, 117, 3156.
5. L. J. W. Shimon, M. Vaida, L. Addadi, M. Lahav and L. Leiserowitz, J. Am. Chem. Soc., 1990, 112, 6215; E. M. D. Keegstra, A. L. Spek, J. W. Zwikker and L. W. Jenneskens, J. Chem. Soc., Chem. Commun., 1994, 1633; G. R. Desiraju, Angew. Chem., Int. Ed. Engl., 1995, 34, 2311.
6. L. J. W. Shimon, M. Vaida, L. Addadi, M. Lahav and L. Leiserowitz, J. Am. Chem. Soc., 1990, 112, 6215; E. M. D. Keegstra, A. L. Spek, J. W. Zwikker and L. W. Jenneskens, J. Chem. Soc., Chem. Commun., 1994, 1633; G. R. Desiraju, Angew. Chem., Int. Ed. Engl., 1995, 34, 2311.
7. G. A. Jeffrey and W. A. Saenger, in Hydrogen Bonding in Biological Structures, Springer-Verlag, Berlin, 1991; Z. S. Derewenda, U. Derewenda and P. M. Kobos, J. Mol. Biol., 1994, 241, 83; Z. S. Derewenda, L. Lee and U. Derewenda, J. Mol. Biol., 1995, 252, 248.
8. G. A. Jeffrey and W. A. Saenger, in Hydrogen Bonding in Biological Structures, Springer-Verlag, Berlin, 1991; Z. S. Derewenda, U. Derewenda and P. M. Kobos, J. Mol. Biol., 1994, 241, 83; Z. S. Derewenda, L. Lee and U. Derewenda, J. Mol. Biol., 1995, 252, 248.
9. G. A. Jeffrey and W. A. Saenger, in Hydrogen Bonding in Biological Structures, Springer-Verlag, Berlin, 1991; Z. S. Derewenda, U. Derewenda and P. M. Kobos, J. Mol. Biol., 1994, 241, 83; Z. S. Derewenda, L. Lee and U. Derewenda, J. Mol. Biol., 1995, 252, 248.
10. T. Steiner and W. Saenger, J. Chem. Soc., Chem. Commun., 1995, 2087; D. Braga, F. Grepioni, J. J. Byrne and A. Wolf, J. Chem. Soc., Chem. Commun., 1995, 125.
11. T. Steiner and W. Saenger, J. Chem. Soc., Chem. Commun., 1995, 2087; D. Braga, F. Grepioni, J. J. Byrne and A. Wolf, J. Chem. Soc., Chem. Commun., 1995, 125.
12. J. A. R. P. Sarma and G. R. Desiraju, Acc. Chem. Res., 1986, 19, 222.
13. G. Müller, M. Lutz and S. Harder, Acta Crystallogr., Sect. B, 1996, 52, 1014.
14. A. K. Abdul-Sada, A. M. Greenway, P. B. Hitchcock, T. J. Mohammed, K. R. Seddon and J. A. Zora, J. Chem. Soc., Chem. Commun, 1986, 1753; A. G. Avent, P. A. Chaloner, M. P. Day, K. R. Seddon and T. Welton, J. Chem. Soc., Dalton Trans., 1994, 23, 3405.
15. A. K. Abdul-Sada, A. M. Greenway, P. B. Hitchcock, T. J. Mohammed, K. R. Seddon and J. A. Zora, J. Chem. Soc., Chem. Commun, 1986, 1753; A. G. Avent, P. A. Chaloner, M. P. Day, K. R. Seddon and T. Welton, J. Chem. Soc., Dalton Trans., 1994, 23, 3405.
16. S. Moran, R. X.-F. Ren, S. Rumney IV and E. T. Kool, J. Am. Chem. Soc., 1997, 119, 2056.
17. T. A. Evans and K. R. Seddon, Chem. Commun., 1997, 2023
18. H. Umeyama and K. Morokuma, J. Am. Chem. Soc., 1977, 99, 1316.
19. G. R. Desiraju, Acc. Chem. Res., 1991, 24, 290; T. Steiner and W. Saenger, J. Am. Chem. Soc., 1992, 114, 10146; T. Steiner and W. Saenger, J. Am. Chem. Soc., 1993, 115, 4540; T. Steiner, Chem. Commun., 1997, 727.
20. G. R. Desiraju, Acc. Chem. Res., 1991, 24, 290; T. Steiner and W. Saenger, J. Am. Chem. Soc., 1992, 114, 10146; T. Steiner and W. Saenger, J. Am. Chem. Soc., 1993, 115, 4540; T. Steiner, Chem. Commun., 1997, 727.
21. G. R. Desiraju, Acc. Chem. Res., 1991, 24, 290; T. Steiner and W. Saenger, J. Am. Chem. Soc., 1992, 114, 10146; T. Steiner and W. Saenger, J. Am. Chem. Soc., 1993, 115, 4540; T. Steiner, Chem. Commun., 1997, 727.
22. G. R. Desiraju, Acc. Chem. Res., 1991, 24, 290; T. Steiner and W. Saenger, J. Am. Chem. Soc., 1992, 114, 10146; T. Steiner and W. Saenger, J. Am. Chem. Soc., 1993, 115, 4540; T. Steiner, Chem. Commun., 1997, 727.
23. G. R. Desiraju, Angew. Chem., Int. Ed. Engl, 1995, 34, 2311.
24. J. J. Novoa, B. Tarron, M.-H. Whangbo and J. M. Williams, J. Chem. Phys., 1991, 95, 5179; T. van Mourik and F. B. van Duijneveldt, J. Mol. Struct. (THEOCHEM), 1995, 341, 63.
25. J. J. Novoa, B. Tarron, M.-H. Whangbo and J. M. Williams, J. Chem. Phys., 1991, 95, 5179; T. van Mourik and F. B. van Duijneveldt, J. Mol. Struct. (THEOCHEM), 1995, 341, 63.
26. K. Hensen, P. Pullmann and J. W. Bats, Z. Anorg. Allg. Chem., 1988, 556, 62; D Mootz and J. Hocken, Z. Naturforsch, Teil B, 1989, 44, 1239.
27. K. Hensen, P. Pullmann and J. W. Bats, Z. Anorg. Allg. Chem., 1988, 556, 62; D Mootz and J. Hocken, Z. Naturforsch, Teil B, 1989, 44, 1239.
28. C. B. Aakeröy and K. R. Seddon, Z. Naturforsch., Teil B, 1993, 48, 1023.
29. T. Steiner, Acta Crystallogr., Sect. B, 1998, 54, 456.
30. Y. V. Zefirov, Crystallogr. Rep., 1998, 43, 283.
31. Cambridge Structural Database version 5.14 (October 1997); F. H. Allen and O. Kennard, Chem. Des. Automat. News, 1993, 8, 3137.
32. Cambridge Structural Database version 5.14 (October 1997); F. H. Allen and O. Kennard, Chem. Des. Automat. News, 1993, 8, 3137.
33. T. Steiner and G. R. Desiraju, Chem. Commun., 1998, 891.
34. T. A. Evans, QUESTPLUS, The Queen's University of Belfast, 1994-1998.
35. J. Kroon and J. A. Kanters, Nature (London), 1974, 248, 667.
36. L. Pauling, The Nature of the Chemical Bond, Cornell University Press, USA, 1947
37. A. Bondi, J. Phys. Chem., 1964, 68, 441.
38. H. F. J. Savage and J. L. Finney, Nature (London), 1986, 322, 717.
39. G. Aullón, D. Bellamy, L. Brammer, E. A. Bruton and G. Orpen, Chem. Commun., 1998, 653.
40. G. R. Desiraju, Crystal Engineering, The Design of Organic Solids, Elsevier, Amsterdam, 1989.
41. T. A. Evans and K. R. Seddon, unpublished work.