Journal of the American Chemical Society p. 5581 - 5583 (1991)
Update date:2022-08-10
Topics:
Shepherd, Brian D.
The relative basicities of ten siloxanes and an ether were studied in benzene by determining from visible spectroscopic measurements the thermodynamic constants for the competition between the substrate and a reference base (4-chloro-2-nitroaniline) for acid (trifluoromethanesulfonic acid): RB-HA + S ? RB + S·HA. The Keq values were considered as a measure of basicity with the following order established and explained by inductive effects in the protonated species: permethyl linear siloxanes (Me3Si(OSiMe2)nOSiMe3, n = 0-3) > dibutyl ether > HMe2SiOSiMe2H > branched siloxanes ((Me3SiO)3SiMe, (Me3SiO)4Si) > cyclic siloxanes ((Me2SiO)n, n = 3-5). The ΔH and ΔS values were positive and increased with higher basicity; this behavior was attributed to differential solvation of ion pairs.
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