Acid dissociation constant
Acidity in nonaqueous solutions
A solvent will be more likely to promote ionization of a dissolved acidic molecule in the following circumstances: It is a protic solvent, capable of forming hydrogen bonds.

Acid dissociation constant

Section Title: Acidity in nonaqueous solutions
Table Section Text: A solvent will be more likely to promote ionization of a dissolved acidic molecule in the following circumstances: It is a protic solvent, capable of forming hydrogen bonds.

HA ⇌ A− + H+	ACN	DMSO	Water

p-Toluenesulfonic acid	8.5	0.9	Strong

2,4-Dinitrophenol	16.66	5.1	3.9

Benzoic acid	21.51	11.1	4.2

Acetic acid	23.51	12.6	4.756

Phenol	29.14	18.0	9.99

BH+ ⇌ B + H+	ACN	DMSO	Water

Pyrrolidine	19.56	10.8	11.4

Triethylamine	18.82	9.0	10.72

Proton sponge	18.62	7.5	12.1

Pyridine	12.53	3.4	5.2

Aniline	10.62	3.6	4.6

Sentence(s)

Proton sponge has a pKₐ value of 12.1.

final_sentence: Proton sponge has a pKₐ value of 12.1.