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User:Itub/Table of pKa's

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These pKa values were extracted from the chemboxes.

1,2,3-Triazole 1.2
1,2,4-Triazole 2.2
1,2-Ethanedithiol ~11
1,8-Bis(dimethylamino)naphthalene 12.1[1]
1-Naphthaleneacetic_acid 4.24 (25 °C)[2]
2-Butoxyethanol high pKa for -OH group
2-Pyridone 11.65
3-Nitroaniline 2.47
Acetic_acid 4.76 at 25 °C
Acetonitrile 25
Acetylene 25
Acrylic_acid 4.25
Adenosine_triphosphate 6.5
Adipic_acid 4.43, 5.41
Ammonium_bromide <7
Aniline 27 (conjugate acid pKa=4.87)
Arsenic_acid 2.19, 6.94, 11.5
Arsenic_trioxide 9.2
Ascorbic_acid 4.17 (first), 11.6 (second)
Azelaic_acid 4.550, 5.598[3]
Azobenzene 3.3
Benzoic_acid 4.21
Benzotriazole 8,37 [4]
Benzylamine 9.33 (value for protonated amine, pKaH)
Bis-tris_methane 5.80-7.30 @25°C
Boric_acid 9.24 (see text)
Bromothymol_blue 7.10
Caffeine −0.13 – 1.22[5]
Caprylic_acid 4.89[6]
Carbendazim 4.48
Carbon_dioxide 6.35 and 10.33
Carbonic_acid 3.60 (see text)
10.25
Chloric_acid ca. −1
Chloroacetic_acid 2.87[7]
Chlorous_acid 1.96
Cinnamic_acid 4.44
Citric_acid pKa1=3.15
pKa2=4.77
pKa3=6.40
Cyclohexanol 16
Cyclopentane ~45
Dichloroacetic_acid 1.25[8]
Diisopropylamine 11.05
Dimethyl_sulfoxide 35
Ethane 50
Ethanol 15.9
Ethyl_acetoacetate 10.68 (in H2O)
14.2 (inDMSO)
Fluoroantimonic_acid −25
Fluoroboric_acid -0.4
Fluoroform 25 - 28
Fluorosulfuric_acid -10
Folic_acid 1st: 2.3, 2nd: 8.3
Formamide 23.5 (in DMSO)[9]
Formic_acid 3.744
Fumaric_acid pka1=3.03, pka2=4.44
Fusaric_acid ?
Gallic_acid COOH: 4.5, OH: 10.
Gluconic_acid 3.86
Glycolic_acid 3.83
HEPES 3 and 7.55
Hexanoic_acid 4.88
Hydrazoic_acid 4.6 to 4.7
Hydrobromic_acid −9
Hydrochloric_acid −8.0
Hydrofluoric_acid 3.15 (inwater)
Hydrogen_bromide ≈ –9
Hydrogen_chloride -4
Hydrogen_cyanide 9.2 - 9.3
Hydrogen_iodide –10
Hydrogen_peroxide 11.65
Hydrogen_selenide 3.89 (11.0 at 25C)
Hydrogen_sulfide 6.89
19±2 (See Text)
Hydronium −1.7
Hypochlorous_acid 7.497[10]
Imidazole pKa=14.5, pKBH+=6.993
Indole 16.2
(21.0 inDMSO)
Iodic_acid 0.75
Isobutylamine (Alkaline) 12.5 at 20°C at 100g/l -->
Isobutyric_acid 4.84 at 20 °C
Isopropyl_alcohol 16.5 for H onhydroxyl
Lactic_acid 3.85
Lithium_diisopropylamide 34
Maleic_acid pka1=1.83, pka2=6.07
Malic_acid pKa1=3.4, pKa2=5.13
Mandelic_acid 3.37
Meta-Chloroperoxybenzoic_acid 7.57
Methanethiol ~10.4
Methanol ~ 15.5
Methylamine 10.64 (value for protonated amine, pKaH)
N-Butylamine (Alkaline) 12.5 at 20°C at 100g/l
N-Butyllithium >35 (need source)
Nitromethane 10.2
Nonanoic_acid 4.96[6]
O-Cresol 10.26
P-Toluenesulfonic_acid -2.8
Pentane ~45
Peracetic_acid 8.20
Perfluorooctanoic_acid 0
Perrhenic_acid -1.25[citation needed]
Phenol 9.95
Phenothiazine approx 23 in DMSO
Phosphoric_acid 2.12, 7.21, 12.67
Phthalimide 8.3
Picric_acid 0.38
Piperazine 5.68, 9.82
Piperidine 11.24
Piperine 1.98[11]
Polylysine 9
Potassium_acetate 9.7 (0.1M solution)
Potassium_manganate 7.1
Propan-1-ol (~16)
Propionic_acid 4.88
Pyrocatechol 9.5
Pyrrolidine 11.27
Rhodium(III)_chloride acidic in solution
Rongalite decomp. at low pH
Sebacic_acid 4.720, 5.450[3]
Sec-Butylamine (Alkaline) 12.3[12]
Selenic_acid similar to H2SO4
Selenium_dioxide 2.62 (H2SeO3⇌HSeO3− + H+)
8.32 (HSeO3−⇌SeO32− + H+)
Silver_oxide -4
Sodium_amide 38 [13]
Sodium_bisulfate 1.9
Sodium_formate 7.0-8.5 (0.1M)
Sodium_persulfate 6.0 (1% solution)
Sorbic_acid 4.76 at 25 °C
Suberic_acid 4.526, 5.498[3]
Sulfamic_acid 1.18 (1% solution @25 °C (77 °F)
Sulfur_dioxide 1.81
Tebufenpyrad 5.9 in water
Tetramethylethylenediamine 8.97
Tetrazole 4.90 [14]
Trichloroacetic_acid 0.77[15]
Triclopyr 2.68
Trifluoroacetic_acid 0.3
Tris 8.1
Urea 26.9
Uric_acid 3.89
Valeric_acid 4.82
Water_(molecule) 15.74
~35-36
Wurster's_blue 6.35
Zinc_peroxide ~7 (3% solution)

References and notes

edit
  1. ^ R. W. Alder, P. S. Bowman, W. R. S. Steele, and D. R. Winterman (1968). "The remarkable basicity of 1,8-bis(dimethylamino)naphthalene". Chem. Commun.: 723. doi:10.1039/C19680000723.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  2. ^ J. Chem. Soc. (1954) 4102
  3. ^ a b c Bretti, C.; Crea, F.; Foti, C.; Sammartano, S. (2006). "Solubility and Activity Coefficients of Acidic and Basic Nonelectrolytes in Aqueous Salt Solutions. 2. Solubility and Activity Coefficients of Suberic, Azelaic, and Sebacic Acids in NaCl(aq), (CH3)4NCl(aq), and (C2H5)4NI(aq) at Different Ionic Strengths and at t=25 C". J. Chem. Eng. Data. 51 (5): 1660–1667. doi:10.1021/je060132t.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  4. ^ Cite error: The named reference SRC was invoked but never defined (see the help page).
  5. ^ This is the pKa for protonated caffeine, given as a range of values included inHarry G. Brittain, Richard J. Prankerd (2007). Profiles of Drug Substances, Excipients and Related Methodology, volume 33: Critical Compilation of Pka Values for Pharmaceutical Substances. Academic Press. ISBN 012260833X.
  6. ^ a b Lide, D. R. (Ed.) (1990). CRC Handbook of Chemistry and Physics (70th Edn.). Boca Raton (FL):CRC Press.
  7. ^ Ionization Constants of Heteroatom Organic Acids
  8. ^ Ionization Constants of Heteroatom Organic Acids
  9. ^ F. G. Bordwell, J. E. Bartmess and J. A. Hautala (1978). "Alkyl effects on equilibrium acidities of carbon acids in protic and dipolar aprotic media and the gas phase". J. Org. Chem. 43 (16): 3095–3101. doi:10.1021/jo00410a001.
  10. ^ Morris, J. C. 1966. The acid ionization constant of HOCl from 5 to 35 °. J. Phys. Chem. 70:3798-3805.
  11. ^ Harry G. Brittain, Richard J. Prankerd (2007). Profiles of Drug Substances, Excipients and Related Methodology, volume 33: Critical Compilation of Pka Values for Pharmaceutical Substances. Academic Press. ISBN 012260833X.
  12. ^ "sec-BUTYLAMINE." Website of chemicalland21.com (accessed 16 April 2007).
  13. ^ Buncel; Menon J. Organomet. Chem. 1977, 141, 1
  14. ^ Phys. Chem. Chem. Phys., 2002, 4, 4314-4318
  15. ^ Ionization Constants of Heteroatom Organic Acids
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