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R-CO2H
pKa 4
Ar-CO2H
pKa 4
CF3-CO2H
pKa 1
R-SO3H
pKa 1
Ar-SO3H
pKa 1
R-OH
pKa 14
Ph-OH
pKa 10
R-SH
pKa 11
H2O
pKa 14
NH3
pKb 5 (3H)
R-NH2
pKb 5 (2H)
R2-NH
pKb 5 (1H)
R3-N
pKb 5 (0H)
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 (3 basic centers)