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Sulfonic acid
pKa = -2 to 1

Phosphonic acid
pKa1 = 1-3
pKa2 = 5-8

Carboxylic acid
pKa = 3-5

Tetrazole
pKa = 4.5-5.5

Sulfonamide
pKa = 7-10

Imide
pKa = 6-9

phenol
pKa = 9-11

thiol
pKa = 8-10.5

Alcohol
pKa = 15-18

Guanidine
pKa = 12-13.5

Amidine
pKa = 11-13

Aliphatic amines
pKa = 8-11

Piperidine
pKa = 10-11.5

Morpholine
pKa = 7-8.5

imidazole
pKa = 6-7.5

pyridine
pKa = 5-6.5

aniline
pKa = 4-6

amide
pKa = -1 to 1

quaternary ammonium
NONE