Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 1, Issue 17, Pages 3094-3101Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/b303453d
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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 x 10(-3), -2.86 x 10(03) and -3.05 x 10(-3), respectively. Given that the relative differences in the slopes are modest, no clear distinction can be made about the relative sigma-donor ability of a C-H bond and a C-C bond.
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