
%0 Journal Article
%A Green, Alison J. 
%A Giordano, Josie 
%A White, Jonathan M. 
%T Gauging the Donor Ability of the C-Si Bond. Results from Low-Temperature Structural Studies of <emph type="2">gauche</emph> and Antiperiplanar &#946;-Trimethylsilyl-cyclohexyl Esters and Ethers by Use of the Variable Oxygen Probe.
%J Australian Journal of Chemistry
%D 2000/07/21
%V 53
%N 4
%P 285-292
%K pKa; silicon substituent; synthesis; X-ray structure.
%R https://doi.org/10.1071/CH99138
%U https://www.publish.csiro.au/paper/CH99138 
%X A plot of C&#8211;OR bond distance against pKa(ROH) for esters and ether derivatives of the antiperiplanar &#946;-silyl alcohol (4) has a slope of &#8211;5.310&#8211;3. This represents a stronger response of the C&#8211;OR distance than was observed for the corresponding gauche &#946;-silyl alcohol (5) and its derivatives. This result is consistent with the greater donor ability of a C&#8211;Si bond compared with a C&#8211;C bond. Comparison of these plots with those previously reported for derivatives (3) of tetrahydropyran-2-ol reveals that a C&#8211;Si bond is a weaker donor than an oxygen non-bonded pair of electrons. An estimate of the pKa value for 2,4-dinitrobenzenesulfenic acid (14) was derived from these plots. 
