Carbon-fluorine compounds

The results of studies of the related fluoroparaffins t-butyl fluoride and tris(trifluoromethyl)methane i (see Table 15) show that the C-F lengths in these molecules compare favourably with their counterparts in Table 14, particularly when allowance is made for the high nominal e.s.d. plus parameter correlation, in t-butyl fluoride. The C-C distances are quite normal for paraffins, suggesting that the electronegativity of fluorine has little effect except on the bonds directly involving fluorine. However, F F non-bonded interactions in (CF3)3CH influence the conformation of the molecule the CF groups are found to be rotated 18° from their staggered positions, and they have 10° torsional amplitudes of vibration about the C-C bonds. 

Stnlevik and E. Thom, Acta Chem. Scand., 1971, 25, 320S. 

In perfluorocyclopropane. C-C = 1.506 0.003 A, little different from the QTclopropane value. TTie C-F length, 1.316 0.001 A, is shorter even 

---

Carbon-Fluorine Compounds Chemistry, Biochemistry, and Biological Activities A Ciba Foundation Symposium, Elsevier Amsterdam, 1972... 

Kent, P.W. In Carbon—Fluorine Compounds. Chemistry. Biochemistry and Biological Activities Ciba Found. Svmp. Elsevier Amsterdam, 1972 pp 169—213. 

Graphite Fluorides and Carbon Fluorine Compounds CRC Press Boca Raton, FL, 1991. 

K. Elliott and J. Birch, eds., "Carbon-Fluorine Compounds," Elsevier, Amsterdam, 1972. 

The present chapter deals with recent advances in carbon-fluorine compounds, in particular focusing on their electrochemical properties. 

T. Nakajima, N. Watanabe, Graphite Fluorides and Carbon-Fluorine Compounds, CRC Press, Inc., Boca Raton, FL, (1991). 

Buffa, P., Guarriero-Bobyleva, V., Pasquali-Ronchetti, J. (1972). Biochemical effects of fluoroacetate poisoning in rat liver. In Carbone-Fluorine Compounds, pp. 303-30. Associated Scientific Compounds, Amsterdam. 

Peters, R.A. (1972). Some metabolic aspects of fluoroacetate especially related to fluorocitrate. In Carbon Fluorine Compounds. A Ciba Foundation Symposium, pp. 55-70. Associated Scientific Publishers., Amsterdam. 

Sharpe, A. The physical properties of the carbon-fluorine bond. In Carbon-fluorine compounds. A Ciba Foundation Symp. Amsterdam Elsevier-Excerpta Medica 1972. 

Wettstein, A. (1972) Chemistry of fluorosteroids and their hormonal properties, in A Ciba Foundation Symposium Carbon-Fluorine Compounds, Elsevier Excerpta Medica, Amsterdam, pp. 281-301. 

Elliott, K. Birch, J. Carbon-Fluorine Compounds Chemistry, Biochemistry and Biological Activities. Amsterdam Elsevier Scientific Publishers, 1972. 

Gibble, G. W. (1973) /. Chem. Educ. 50,460-462 ElHott, K., and Birch, eds. (1972) Carbon-Fluorine Compounds, Elsevier, Amsterdam... 

Taylor, N.F.in Ciba Fdn. Svmp Carbon-Fluorine Compounds. Elsevier and Associated Scientific Publishers, Amsterdam, 1972, 212-38. 

Dwek, R.A. in Ciba Found. Svmp Carbon-Fluorine Compounds. 1972, 239-79. 

Kent, P.W. Chem. Ind. (London 1969, 1128-1132. Barnett, J.E.G. In Ciba Fdn. Symo. Carbon Fluorine Compounds Elsevier Associated Scientific Publishers, Amsterdam, 1972 95-115. 

Dwek, R.A. In Ciba Fdn. Symp. Carbon Fluorine Compounds Elsevier Associated Scientific... 

Ihe diverse chemical, biological, and industrial applications of the numerous synthetic carbon-fluorine compounds are almost legendary. In 1944, Marais identified fluoroacetate in the leaves of the South African shrub Dichapetalum cymosum since then chemists and biologists continue to be intrigued by the natural occurrence, synthesis, and properties of the C-F bond. 

Fluorine is used to prepare fluorocarbons— very stable carbon—fluorine compounds used as refrigerants, lubricants, and plastics. Teflon ( FIGURE 22.9) is a polymeric fluorocarbon noted for its high thermal stability and lack of chemical reactivity. 

It is clear from the discussion in this section that there are a great many gaps in our knowledge and understanding of the molecular struchues of carbon-fluorine compounds. 

---