38679-99-1Relevant academic research and scientific papers
Low-temperature x-ray structural studies of the ester and ether derivatives of cis- and trans-4-tert-butyl cyclohexanol and 2-adamantanol: Application of the variable oxygen probe to determine the relative σ-donor ability of C-H and C-C bonds
Spiniello, Marisa,White, Jonathan M.
, p. 3094 - 3101 (2003)
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 pKa(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.
