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Alcohols
pKa 16-19
ALWAYS UNIONIZED AT pH 2 OR 7.4
Carboxylic acid
pKa 5
Ionized at pH 7.4
Unionized at pH 2
Amine
pKa 10
Ionized at both pH 7.4 and 2

Phenol
pKa 9-11
Weak acid - unionized at pH 7.2 and 2

Sulfonamide
pKa 9-10
Weak acid - unionized at pH 7.2 and 2

Imide
pKa 9-10
Weak acid- unionized at pH 7.2 and 2

Alkylthiol
pKa 10-11
Weak acid - unionized at pH 7.2 and 2

Thiophenol
pKa 9-10
Weak acid - unionized at pH 7.2 and 2

N-arylsulfonamide
pKA 6-7 ;)
Weak acid
Unionized at pH 2
Ionized at pH 7.4

sulfonimide
pKa 5-6
Weak acid
Unionized at pH 2
Ionized at pH 7.4

Alkylcarboxylic acid
pKa 5-6
Weak acid
Unionized at pH 2
Ionized at pH 7.4

arylcarboxylic acid
pKa 4-5
Unionized at pH 2
Ionized at pH 7.4

Sulfonic acid
Weak acid
pKa 0-1
Ionized at pH 2 and 7.4

aniline
Weak base
pKa 4.6
ionized at pH 2
Unionized at pH 7.4

alkylamines
pKa 10-11 if secondary
pKa 9-10 if primary
Ionized at pH 2 and 7.4

Amidine
pKa 10-11
Ionized at pH 2 and 7.4

Guanidine
pKa 12-13
Ionized at pH 2 and 7.4