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pKa Values
For complex chelating agents, see also reference 77.
Note. This document was compiled by W.P. Jencks and has been added to by F.H. Westheimer Compound
* Indicates a thermodynamic value. PHOSPHATES AND PHOSPHONATES
Phosphates
Compound
Arylphosphonic acids
Phosphonates
H2O3PCH2CH(CH3)PO3H2 <2, 2.6, 7.00, 9.27 57 **These values were obtained in 50% ethanol.
(a) The compounds were not sufficiently soluble.
For graphical plots of a large number of substituted Acetic acids, substituted
Phosphonates (Ref. 2)
-NH3+ -NH3+
Phosphines in acetonitrile, see ref. 89.
CARBOXYLIC ACIDS
Aliphatic
Compound
Unsaturated acids (25°)
Compound

Compound
Unsaturated acids, Cis- and Trans-
Dicarboxylic acids, unsaturated*
Maleic
Alicyclic Dicarboxylic acids
Itaconic (1-Propene-2-3-dicarboxylic acid) Aliphatic
Alicyclic Dicarboxylic acids
Compound
Compound
Dicarboxylic acids*
oxalic
Aliphatic
Bicyclo[2.2.2]octane-1-carboxylic acids, 4-
substituted
Lysergic acid, etc.
Hydroxycyclohexanecarboxylic acids
Aromatic
Substituted benzoic acids (ref. 2)
*thermodynamicfor complex chelating agents, see also ref. 84.
Benzoic acid
see also page 9a for more carboxylic acids.
Ortho-substituted benzoic acids
Benzoic acid
Benzene Polycarboxylic acids
Position of carboxyl pKI
Carboxylic Acids
N-2-sulfoethyliminodiacetic 1.92, 2.28, 8.16 Di-(carboxymethyl)-aminomethyl phosphonic Compound
Compound
4,5-dihydroxybenzene-1,3 disulphonic acid 7.66 ALCOHOLS and other OXYGEN ACIDS
Alcohols
Compound
Compound
Triphenylmethanols in H2SO4 HC1O4 HNO3 ref
Unsubstituted triphenyl-
Substituent effects for ionization of RCH2OH
Hydroxamic acids
Other oxygen acids
OTHER OXYGEN ACIDS
Hydroxamic acids
Aceto-
Compound
Pyridine oxides
5-Methyl-1,2,3-cyclohexanetrione-1,3-dioxime 5-Methyl-1,2,3-cyclohexane-trionetrioxime 2-Methylamino-1-methoxypyridinium toluene-p-sulphonate Oxygen acids
sulfinic acids
Pyridine 1-oxides
Peroxyacids
Peroxides ROOH (Ref. 70)
H
2-Pyrrolidoone-5-carboxylic acid (glucamicacid) Hydroxamic acids
Amino Acids
Compound
Peptides
Compound
-NH2 Ref.
Compound
NITROGEN COMPOUNDS
Aliphatic Amines pK

X(CH2)2NH3
X(CH2)3NH3
X(CH2)4NH3
X(CH2)5NH3
Secondary amines
Aliphatic Amines
Secondary Amines
Tertiary amines
1-Diethylamino-hexane-thiol-(6)
Cyanoamines
Phenylethylamines
For complex chelating agents of aliphatic amines, N-methyl-2-(3,4-dihydroxyphenyl)-ethylamine Fluoro-substituted amines
Ring amines and imines (in 80% methyl cellosolve) (ref. 2)
Pentamethylene
Amines other
Anilines
Monosubstituted
Substituent
Dimethyl
H
Dimethyl (in 50% ethanol)
Substituent XC6H4N(CH3)2
Ortho-substituted anilines (in 50% ethanol)
Substituted Naphthylamines
N-substituted anilines*
C6H5N(CH3)R C6H5NR2 2-CH3C6H4NHR
2-CH3C6H4NR2
Secondary amines
N-Butylaminoacetic acid
Primary amines
N,N'-di-n-propylethylenediamine 8.14, 10.97 Ethylenediamine-N,N'-diacetic acid 6.42, 9.46 1,3-diamino-2,2-dimethylpropane 8.18, 10.22 Ethylenediamine-N,N-diacetic acid 5.58, 11.05Furfurylamine Tertiary amines
2-(2-hydroxypropylamino)-ethylamine 6.94, Methyl-α-amino-β-mercaptoproionate 6.56, N-2-hydroxyethyliminodiacetic acid 2.2, 8.73 ANILINES (Ref. 88)
m-Substituted anilines
NAPHTHALAMINES
substituted naphthalamines
2-naphthalamine

2-naphthalamine
Anilines (in 50% ethanol)
Unhindered
5-Methylcytosine deoxyriboside 5'-phosphate Hindered
o-Aminophenols
Indicators
N,N-Dimethyl-2,4-dinitroaniline -1.00, -- Heterocyclics
Nucleosides, etc.
Heterocyclics
Acridine
a 50% ethanol; ref. 398-amino-1,2-benzacridine Heterocyclics
hydantoin
Imidazoles
isoQuinolines
Pyridines
Carbobenzoxy-L-histidyl-L-tyrosine ethylester 1-Methylpyrid-4-one benzylimine 9.89 464-COO– Pyridine N-oxides (see oxygen acids) Substituted Pyridines
Pyridine

Ortho-Substituted Pyridines (in 50% ethanol)
Substituent
For complex chelating agents, see also ref. 77 Heterocyclics
Pyrazines
Miscellaneous
Quinoline
Quinoline
Quinazoline
SPECIAL NITROGEN COMPOUNDS
Hydroxylamines
Hydroxylamine
Heterocyclics
Quinoxaline
Hydrazines (30°)
Nitrogen compounds, miscellaneous
Other
S-Methylisothiourea
Hydrazones Hydrazone of:
Cinchona Alkaloids (in 80% aqueous methyl
Semicarbazones of:
Amidoximes
Ox-
Mercaptans, RSH
R
CH3CCH2-
CARBON ACIDS
Bis-( -Diketones):[(RCO)(R'CO)CH]2CHR (in 50% dioxane)
Bis-( -Diketones) (RCO)-(R'CO)CH-Y-CH(COR)(COR') (in 50% dioxane)
Bis-( -Diketones) RCOCH2CO-Y-COCH2COR (in 75% dioxane)
Indicators
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