Thermodynamic Effects of Fluorine As a Substituent in Alkenes
Thermodynamic Effects of Fluorine As a Substituent in Alkenes
Medinger, Karl S
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Assuming two such gauche effects in 18, and using the AH for 17 ^=:± 18, one can estimate the group value for [C-Y^CC^] (equation 17). gauche corr. (18) = -0.82 16 [C-F^CCj^] = -103.9 17 Previously, it was shown that a fluoroalkyl group value could be converted to a f luoroallylic group value by estimating the destabilization per fluorine, which was estimated to be 0.5 per fluorine. Assuming that the effect is the same whether the fluorines are on a terminal car- bon or on an internal carbon, a...llows one to estimate [C-F^C^] (equation 18). [C-F2C2] = -104.9 18 The group values estimated in this work are siommarized below. 38 Equation [C-H2FC] - -52.7 1 (C-HF2C] = -108.6 2 [C-F3C] = -167.8 3 [C-F2C2] = -104.9 18 [C-H2FCJJ] = -52.2 12 [C-HF^Cj^] = -107.6 10 [C-FgCj^] = -166.0 11 [C-F^CCj^] = -103.9 17 [Cj^-HF] = -38.4 13 [CJ5-F2] = -88.0 15 cis corr. (CHF2 cis to CH2) = 1.37 6 cis corr. (CF^ cis to CE^) = 1.63 7 cis corr. (F cis to CHo) = -0.64 14 gauche corr. (22) =0.89 8 gauche corr. (25) = 1.05 9 gauche corr.
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