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Volumn 3, Issue 1, 1997, Pages 89-98

Organic fluorine hardly ever accepts hydrogen bonds

Author keywords

ab initio calculations; Cambridge structural database; fluorine compounds; hydrogen bonds; protein data bank

Indexed keywords


EID: 0030937244     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.19970030115     Document Type: Article
Times cited : (939)

References (82)
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    • Note that fluoroalkanes are even more hydrophobic than hydrocarbons: for example, the solubility of tetrafluoromethane in water is only about a seventh of that of methane (on a mol basis); J. H. Hildebrand, J. M. Prausnitz, R. L. Scott, Regular and Related Solutions, Van Nostrand Reinhold, New York, 1970, p. 204.
    • (1970) Regular and Related Solutions , pp. 204
    • Hildebrand, J.H.1    Prausnitz, J.M.2    Scott, R.L.3
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    • note
    • CSD User Manuals; Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, UK.
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    • To correct for the systematic shortening of X-H bonds measured by X-ray diffraction, normalized H-atom positions were used throughout this study. They are obtained by moving the H atom position along the observed X-H bond direction so that the X-H distance is equal to the standard neutron-diffraction value (0.983 Å for O-H, 1.009 Å for N-H): a) G. A. Jeffrey, L. Lewis, Carhohydr. Res. 1978, 60, 179;
    • (1978) Carhohydr. Res. , vol.60 , pp. 179
    • Jeffrey, G.A.1    Lewis, L.2
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    • Ref. [6a], p. 187
    • Ref. [6a], p. 187.
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    • Tripos Associates, St Louis, MO
    • Tripos Associates, St Louis, MO.
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    • University of Cambridge, UK
    • R. D. Amos, 1994, CADPAC4.2, University of Cambridge, UK.
    • (1994) CADPAC4.2
    • Amos, R.D.1
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    • note
    • Throughout the text, small molecule and protein crystal structures will be referred to by their CSD and PDB reference codes, respectively (refs. [7,8]).
  • 58
    • 0342375398 scopus 로고    scopus 로고
    • 2 the F atoms play no part in the respective hydrogen-bonding patterns. The structures show only O-H ⋯ O and N-H ⋯ N hydrogen bonds; M. K. Klapdor, H. Willner, W. Poll, D. Mootz, Angew. Chem. 1996, 108, 336; Angew. Chem. Int. Ed. Engl. 1996, 35, 320; W. Poll, G. Pawelke, D. Mootz, E. H. Appelman, ibid. 1988, 100, 425 and Angew. Chem. Int. Ed. Engl. 1988, 27, 392.
    • (1996) Angew. Chem. , vol.108 , pp. 336
    • Klapdor, M.K.1    Willner, H.2    Poll, W.3    Mootz, D.4
  • 59
    • 33748240891 scopus 로고    scopus 로고
    • 2 the F atoms play no part in the respective hydrogen-bonding patterns. The structures show only O-H ⋯ O and N-H ⋯ N hydrogen bonds; M. K. Klapdor, H. Willner, W. Poll, D. Mootz, Angew. Chem. 1996, 108, 336; Angew. Chem. Int. Ed. Engl. 1996, 35, 320; W. Poll, G. Pawelke, D. Mootz, E. H. Appelman, ibid. 1988, 100, 425 and Angew. Chem. Int. Ed. Engl. 1988, 27, 392.
    • (1996) Angew. Chem. Int. Ed. Engl. , vol.35 , pp. 320
  • 60
    • 0343245056 scopus 로고
    • 2 the F atoms play no part in the respective hydrogen-bonding patterns. The structures show only O-H ⋯ O and N-H ⋯ N hydrogen bonds; M. K. Klapdor, H. Willner, W. Poll, D. Mootz, Angew. Chem. 1996, 108, 336; Angew. Chem. Int. Ed. Engl. 1996, 35, 320; W. Poll, G. Pawelke, D. Mootz, E. H. Appelman, ibid. 1988, 100, 425 and Angew. Chem. Int. Ed. Engl. 1988, 27, 392.
    • (1988) Angew. Chem. Int. Ed. Engl. , vol.100 , pp. 425
    • Poll, W.1    Pawelke, G.2    Mootz, D.3    Appelman, E.H.4
  • 61
    • 84990167974 scopus 로고
    • 2 the F atoms play no part in the respective hydrogen-bonding patterns. The structures show only O-H ⋯ O and N-H ⋯ N hydrogen bonds; M. K. Klapdor, H. Willner, W. Poll, D. Mootz, Angew. Chem. 1996, 108, 336; Angew. Chem. Int. Ed. Engl. 1996, 35, 320; W. Poll, G. Pawelke, D. Mootz, E. H. Appelman, ibid. 1988, 100, 425 and Angew. Chem. Int. Ed. Engl. 1988, 27, 392.
    • (1988) Angew. Chem. Int. Ed. Engl. , vol.27 , pp. 392
  • 73
    • 0000955395 scopus 로고
    • American Chemical Society, Washington, DC
    • It is remarkable that in spite of their shared hydrophobicity, hydrocarbons and fluorocarbons show even stronger mutual phobicity: P. Mukerjee, K. J. Mysels, ACS Symposia Series 9, American Chemical Society, Washington, DC, 1975 p. 239; P. Mukerjee, Colloids and Surfaces A: Physicochemical and Engineering Aspects 1994, 84, 1.
    • (1975) ACS Symposia Series , vol.9 , pp. 239
    • Mukerjee, P.1    Mysels, K.J.2
  • 74
    • 0028409408 scopus 로고
    • It is remarkable that in spite of their shared hydrophobicity, hydrocarbons and fluorocarbons show even stronger mutual phobicity: P. Mukerjee, K. J. Mysels, ACS Symposia Series 9, American Chemical Society, Washington, DC, 1975 p. 239; P. Mukerjee, Colloids and Surfaces A: Physicochemical and Engineering Aspects 1994, 84, 1.
    • (1994) Colloids and Surfaces A: Physicochemical and Engineering Aspects , vol.84 , pp. 1
    • Mukerjee, P.1
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    • Dechema, Frankfurt/Main
    • To keep perspective, we note that the mutual solubilities of benzene and water are areater than those of fluorobenzene and water; J. M. Sorensen, W. Arlt, Liquid-Liquid Equilibrium Data Collection, Binary Systems, Chemistry Data Series, Vol. 5, Part 1, Dechema, Frankfurt/Main, 1979. Clearly, in the liquid, other geometric arrangements and other sorts of interactions are involved.
    • (1979) Liquid-Liquid Equilibrium Data Collection, Binary Systems, Chemistry Data Series , vol.5 , Issue.1 PART
    • Sorensen, J.M.1    Arlt, W.2
  • 79
    • 0343245052 scopus 로고
    • SERC Daresbury Laboratory, Daresbury, UK
    • For example, the calculated Mulliken charges on the oxygen atoms of formaldehyde and benzaldehyde are -0.44 and -0.51, respectively. These may he compared with the partial charges on the fluorine atoms of fluoromethane (-0.39) and fluorobenzene (-0.38). In methyl trifluoroacetate, the fluorine atoms have partial charges of -0.36, while the charges on the oxygens are -0.54 and -0.61. Charges calculated with GAMESS-UK (M. F. Guest, P. Sherwood, GAMESS Users Guide, SERC Daresbury Laboratory, Daresbury, UK, 1990) at the 6-31G* basis set level.
    • (1990) GAMESS Users Guide
    • Guest, M.F.1    Sherwood, P.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.