Carbanion
Carbon acids
Any compound containing hydrogen can, in principle, undergo deprotonation to form its conjugate base. A compound is a carbon acid if deprotonation results in loss of a proton from a carbon atom.

Carbanion

Section Title: Carbon acids
Table Section Text: Any compound containing hydrogen can, in principle, undergo deprotonation to form its conjugate base. A compound is a carbon acid if deprotonation results in loss of a proton from a carbon atom.

name	formula	structural formula	pKaDMSO

Cyclohexane	C6H12	-	~ 60

Methane	CH4	-	~ 56

Benzene	C6H6	-	~ 49

Propene	C3H6	-	~ 44

Toluene	C6H5CH3	-	~ 43

Ammonia (N-H)	NH3	-	~ 41

Dithiane	C4H8S2	-	~ 39

Dimethyl sulfoxide	(CH3)2SO	-	35.1

Diphenylmethane	C13H12	-	32.3

Acetonitrile	CH3CN	-	31.3

Aniline (N-H)	C6H5NH2	-	30.6

Triphenylmethane	C19H16	-	30.6

Fluoroform	CHF3	-	30.5

Xanthene	C13H10O	-	30.0

Ethanol (O-H)	C2H5OH	-	29.8

Phenylacetylene	C8H6	-	28.8

Thioxanthene	C13H10S	-	28.6

Acetone	C3H6O	-	26.5

Chloroform	CHCl3	-	24.4

Benzoxazole	C7H5NO	-	24.4

Fluorene	C13H10	-	22.6

Indene	C9H8	-	20.1

Cyclopentadiene	C5H6	-	18.0

Nitromethane	CH3NO2	-	17.2

Diethyl malonate	C7H12O4	-	16.4

Acetylacetone	(H3CC(O))2CH2	-	13.3

Hydrogen cyanide	HCN	-	12.9

Acetic acid (O-H)	CH3COOH	-	12.6

Malononitrile	C3H2N2	-	11.1

Dimedone	C8H12O2	-	10.3

Meldrum's acid	C6H8O4	-	7.3

Hexafluoroacetylacetone	(F3CC(O))2CH2	-	2.3

Hydrogen chloride (Cl-H)	HCl	HCl (g)	–2.0

Triflidic acid	HC(SO2CF3)3	-	~ –16

Table 1. Carbon acid acidities by pKa in DMSO. These values may differ significantly from aqueous pKa values.

Sentence(s)

The diphenylmethane has pKₐ DMSO of 32.3.
Diphenylmethane's pKₐDMSO is 32.3.

final_sentence: The diphenylmethane has pKₐ DMSO of 32.3.
final_sentence: Diphenylmethane's pKₐDMSO is 32.3.