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Volumn 1, Issue 4, 2001, Pages 277-290

Understanding the Behavior of Halogens as Hydrogen Bond Acceptors

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EID: 0000243556     PISSN: 15287483     EISSN: None     Source Type: Journal    
DOI: 10.1021/cg015522k     Document Type: Article
Times cited : (640)

References (86)
  • 29
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    • (a) For a discussion of the protonation of metal halides, see: Kuhlman, R. Coord. Chem. Rev. 1997, 167, 205.
    • (1997) Coord. Chem. Rev. , vol.167 , pp. 205
    • Kuhlman, R.1
  • 46
    • 0345954819 scopus 로고    scopus 로고
    • C-H⋯Cl-C, R factor ≤0.070 and sigflag <3; C-H⋯ F-C R factor ≤0.060 and sigflag ≤3; C-H⋯Cl-M, R factor ≤0.040 and sigflag <3
    • (a) C-H⋯Cl-C, R factor ≤0.070 and sigflag <3; C-H⋯ F-C R factor ≤0.060 and sigflag ≤3; C-H⋯Cl-M, R factor ≤0.040 and sigflag <3.
  • 50
    • 0003689963 scopus 로고
    • GAMESS-UK is a package of ab initio programs written by: Guest, M. F.; van Lenthe, J. H.; Kendrick, J.; Schoffel, K.; Sherwood, P. with contributions from Amos, R. D.; Buenker, R. J.; van Dam, H. J.J.; Dupuis, M.; Handy, N. C.; Hillier, I. H.; Knowles, P. J.; Bonacic-Koutecky, V.; von Niessen, W.; Harrison, R. J.; Rendell, A. P.; Saunders, V. R.; Stone, A. J.; de Vries, A. H. The package is derived from the original GAMESS code of: Program No. QG01 (GAMESS)
    • (a) GAMESS-UK is a package of ab initio programs written by: Guest, M. F.; van Lenthe, J. H.; Kendrick, J.; Schoffel, K.; Sherwood, P. with contributions from Amos, R. D.; Buenker, R. J.; van Dam, H. J.J.; Dupuis, M.; Handy, N. C.; Hillier, I. H.; Knowles, P. J.; Bonacic-Koutecky, V.; von Niessen, W.; Harrison, R. J.; Rendell, A. P.; Saunders, V. R.; Stone, A. J.; de Vries, A. H. The package is derived from the original GAMESS code of: Dupuis, M.; Spangler, D.; Wendoloski, J. NRCC Software Catalog, Vol. 1, Program No. QG01 (GAMESS), 1980.
    • (1980) NRCC Software Catalog , vol.1
    • Dupuis, M.1    Spangler, D.2    Wendoloski, J.3
  • 52
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    • and references therein
    • (c) Sadlej, A. J. Theor. Chim. Acta 1992, 81, 45 and references therein.
    • (1992) Theor. Chim. Acta , vol.81 , pp. 45
    • Sadlej, A.J.1
  • 56
    • 0345954817 scopus 로고    scopus 로고
    • Basis sets were obtained from the Extensible Computational Chemistry Environment Basis Set Database, Version 1.0, as developed and distributed by the Molecular Science Computing Facility, Environmental and Molecular Sciences Laboratory, which is part of the Pacific Northwest Laboratory, P.O. Box 999, Richland, WA 99352, and funded by the U.S. Department of Energy. The Pacific Northwest Laboratory is a multiprogram laboratory operated by Battelle Memorial Institute for the U.S. Department of Energy under Contract DE-AC06-76RLO 1830. Contact David Feller, Karen Schuchardt, or Don Jones for further information
    • (g) Basis sets were obtained from the Extensible Computational Chemistry Environment Basis Set Database, Version 1.0, as developed and distributed by the Molecular Science Computing Facility, Environmental and Molecular Sciences Laboratory, which is part of the Pacific Northwest Laboratory, P.O. Box 999, Richland, WA 99352, and funded by the U.S. Department of Energy. The Pacific Northwest Laboratory is a multiprogram laboratory operated by Battelle Memorial Institute for the U.S. Department of Energy under Contract DE-AC06-76RLO 1830. Contact David Feller, Karen Schuchardt, or Don Jones for further information.
  • 58
    • 0345954818 scopus 로고    scopus 로고
    • 25 assigns what is almost certainly an unrealistic importance to this single observation. To a lesser extent the same could be said of the smaller spike at 155° in the (O)H⋯Br-M histogram, since this is derived from only two observations
    • 25 assigns what is almost certainly an unrealistic importance to this single observation. To a lesser extent the same could be said of the smaller spike at 155° in the (O)H⋯Br-M histogram, since this is derived from only two observations.
  • 61
    • 0000553568 scopus 로고
    • -, exhibits an even stronger hydrogen bond, calculated at 39 kcal/mol: Gronert, S. J. Am. Chem. Soc. 1993, 115, 10258.
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 10258
    • Gronert, S.1
  • 62
    • 0347216096 scopus 로고    scopus 로고
    • 30b removal of these structures has no effect on the trends in geometry already reported
    • 30b removal of these structures has no effect on the trends in geometry already reported,
  • 65
    • 0345954812 scopus 로고    scopus 로고
    • 1b in which idealized geometries were used. Optimized geometries are provided in the Supporting Information
    • 1b in which idealized geometries were used. Optimized geometries are provided in the Supporting Information.
  • 66
    • 0345954809 scopus 로고    scopus 로고
    • Examination of the variation of H⋯Cl-M angle with increasing coordination number at the metal suggests that there is a small steric effect on this angle arising from repulsions between ligands cis to the halide and the hydrogen bond donor group. This effect is anticipated to be greater for fluorine than for chlorine due to the shorter F-M and H⋯F distances involved, but appears to be insufficient to account for the differences in H⋯X-M angle observed between fluorine and the other halogens
    • Examination of the variation of H⋯Cl-M angle with increasing coordination number at the metal suggests that there is a small steric effect on this angle arising from repulsions between ligands cis to the halide and the hydrogen bond donor group. This effect is anticipated to be greater for fluorine than for chlorine due to the shorter F-M and H⋯F distances involved, but appears to be insufficient to account for the differences in H⋯X-M angle observed between fluorine and the other halogens.
  • 67
    • 0346586074 scopus 로고    scopus 로고
    • 34b,c
    • 34b,c
  • 70
    • 0345954808 scopus 로고    scopus 로고
    • This failure of O-H⋯X-C interactions to follow anticipated trends in H⋯X-C angle is consistent with the anomalous behavior observed for H⋯X distance trends in Q-H⋯X-C interactions (see prior discussion and footnote 30)
    • (a) This failure of O-H⋯X-C interactions to follow anticipated trends in H⋯X-C angle is consistent with the anomalous behavior observed for H⋯X distance trends in Q-H⋯X-C interactions (see prior discussion and footnote 30).
  • 71
    • 0347216098 scopus 로고    scopus 로고
    • The two observations of N-H⋯I-C interactions exhibit H⋯I-C angles in the range 90-110°, while the four O-H⋯I-C interactions have angles of 80-120°
    • (b) The two observations of N-H⋯I-C interactions exhibit H⋯I-C angles in the range 90-110°, while the four O-H⋯I-C interactions have angles of 80-120°.
  • 72
    • 0345954810 scopus 로고    scopus 로고
    • 2 can be traced to a qualitative similarity between the orbital descriptions of M-X and C-X σ-bonds
    • 2 can be traced to a qualitative similarity between the orbital descriptions of M-X and C-X σ-bonds.
  • 78
    • 0345954811 scopus 로고    scopus 로고
    • Personal communication
    • Strauss, S. H. Personal communication.
    • Strauss, S.H.1
  • 79
    • 0347216097 scopus 로고    scopus 로고
    • Brammer, L. Unpublished work
    • Brammer, L. Unpublished work.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.