Organic & Biomolecular Chemistry 2003-09-07

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 sigma-donor ability of C-H and C-C bonds.

Marisa Spiniello, Jonathan M White

文献索引：Org. Biomol. Chem. 1(17) , 3094-101, (2003)

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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 pKa(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(-3) 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.

相关化合物

  • 2-金刚烷醇

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