Low-temperature X-ray structural studies of the ester and ether derivatives of cis- and trans-4-tert-butyl cyclohexanol and 2-adamantanol:L application of the variable oxygen probe to determine the relative σ-donor ability of C-H and C-C bonds

摘要

Results of low-temperature X-ray structural studies for five cis-, and three trans-4-tert-butyl cyclohexanol, and six 2-adamantanol ester and ether derivatives are reported. Plots of C-OR bond distance against pK_a(ROH) for derivatives of axial alcohol (5), equatorial alcohol (6) and 2-adamantanol derivatives (7) give slopes of -2.77 * 10~(-3), -2.86 * 10~(-3) and -3.05 * 10~(-3), respectively. Given that the relative differences in the slopes are modest, no clear distinction can be made about the relative σ-donor ability of a C-H bond and a C-C bond.