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RCO2H, ArCO2H
pKa 4
RSO3H, ArSO3H
pKa -1
ROH
pKa 14
PhOH
pKa 10
RSH
pKa -11
H2O
pKa 14
NH3, NH2, R2NH, R3N
pKb 5
imidazole
pKb 7
pyridine
pKb -9
aniline
pKb -10
DBU (amidine base)
pKb -2
guanidine
pKb -1
pyrrole
pKb 14
pyrrolidine
pKb -3
purine
pKb 4, 5, ~12
CF3CO2H
pKa -1