Paper
Bond length and reactivity. The effect of β-fluorine. Structures of the 4-phenylbenzoate, the diphenyl phosphate and the 2-naphthalenesulfonate esters of trans-2-fluorocyclohexanol
Published May 15, 1992 · P. Jones, A. Kirby, J. Parker
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Abstract
trans-2-Fluorocyclohexyl 4-phenyl- benzoate, (1), Cl9H19FO2, M r = 298.36, monoclinic, P21/n, a = 6.9710 (1), b = 9.3896 (11), c = 23.826 (4) A,/3 = 93.518 (12) °, V= 1556.6/~3, Z = 4, Dx = 1.273 Mg m -a, A(Mo Ka) = 0.71069/~, /z = 0.08 mm-1, F(000) = 632, T = 293 K. Final R = 0.062 for 2396 unique observed reflections, trans-2- Fluorocyclohexyl diphenyl phosphate, (2), C18H2oFOaP, Mr=350.32, monoclinic, Cc, a= 16.644 (5), b = 9.27'.(3), c = 12.048 (4) A, /3 = 109.80 (3) °, V = 1750 A 3, Z = 4, Dx = 1.329 Mg m- A(Mo Ka) = 0.71069 A, /~ = 0.18 mm -1, F(000) = 736, T= 293 K. Final R = 0.029 for 2977 unique observed reflections, trans-2-Fluorocyclohexyl 2- naphthalenesulfonate, (3), C16HITFO35, Mr = 308.37, monocliuic, P21/c, a = 11.7709 (15), b= 15.601 (2), c = 8.2119 (12) A,/3=94.728(15) °, V= 1502.9 A 3, Z = 4, Dx = 1.363 Mg m -3, a(Mo Ka) = 0.71069 A,/z = 0.22 mm-1, F(000) = 648, T = 293 K. Final R = 0.053 for 2098 unique observed reflections. The three related structures have both substituents equatorial, and C--F thus gauche to the C---OX bond. The introduction of the 2-fluorine atom is associated with a significant shortening of the C---O bond only in the sulfonate ester.
The 2-fluorine atom significantly shortens the C-O bond in trans-2-fluorocyclohexanol's 2-naphthalenesulfonate ester, affecting bond length and reactivity.
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