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Table 1.

Properties of the Tested Fluoroalcohols and Their Nonfluorinated Counterparts

Namea Structureb pKac D (mM)d Kpe malcf
Ethanol graphic file with name fx1.gif 15.9 147 ± 13 1.9 ± 3.3 0.20
2-Propanol graphic file with name fx2.gif 16.5 93.3 ± 5.9 4.9 ± 2.4 0.29
tert-Butanol graphic file with name fx3.gif 16.5 48.3 ± 4.5 7.9 ± 1.3 0.26
TFE graphic file with name fx4.gif 12.4 54.3 ± 1.8 (pH 7) 7.2 ± 4.4 0.26
51.9 ± 6.8 (pH 4)
HFIP graphic file with name fx5.gif 9.3 5.6 ± 0.4 (pH 7) 66.7 ± 4.9 0.25
7.8 ± 1.0 (pH 4)
PFTB graphic file with name fx6.gif 5.4 1.4 ± 0.2 (pH 7) 878 ± 10 0.49
2.1 ± 0.3 (pH 4)
a

Name, alcohol name.

b

Structures were drawn using MarvinSketch 5.0.3 from ChemAxon (Budapest, Hungary).

c

pKa, the logarithmic acid dissociation constant; values from (71) to (72) for the regular and fluoroalcohols, respectively.

d

D, the concentration ± fit error (in mM) at which the alcohols double the fluorescence quench rate at pH 7.0 (and also at pH 4.0 for the fluoroalcohols).

e

Kp, the alcohol bilayer/aqueous phase partition coefficients (Kp) as determined by lipid depletion in the stopped flow assay (mean ± SD).

f

malc, the mole-fraction of alcohol in the bilayer at D.