Organofluorine Chemistry

Part of the series Topics in Applied Chemistry pp 57-88

Characteristics of C-F Systems

  • Bruce E. SmartAffiliated withDuPont Central Research and Development, Experimental Station

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The physical properties and chemical reactivities of organic molecules can be dramatically affected by fluorination. Today’s diverse commercial applications of organo-fluorine materials clearly manifest the possible beneficial effects of fluorination, and the numerous ways in which industry has taken practical advantage of these effects are the subjects of the following chapters in this book. This chapter focuses on the characteristic substituent effects that underlie the physicochemical properties of organofluorine compounds, especially those important to the design of commercial products. Fortunately, advances in both experimental and theoretical physical organofluorine chemistry over the past two decades have made the “unusual” behavior of fluorinated compounds much more understandable and predictable. General principles that govern the characteristic effects of fluorination will be presented, but important exceptions also will be noted. Misleading generalizations like “fluorination increases lipophilicity” and myths about fluorine steric effects will be dispelled, for example.