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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.
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Dechema, Frankfurt/Main
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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.
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0343245052
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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.
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GAMESS Users Guide
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Guest, M.F.1
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J. Bernstein, M. C. Etter, L. Leiserowitz, in Structure Correlation, Vol. 2 (Eds: H.-B. Buergi, J. D. Dunitz), VCH, Weinheim, 1994, p. 432.
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A similar opinion has recently been expressed by G. Gilli, Program and Abstracts of NATO Advanced Research Workshop on Crystals: Supramolecular Materials, Sestri Levante, Italy, Aug 31-Sept 4, 1995, p.36.
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Gilli, G.1
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