DISSOCIATION CONSTANTS OF INORGANIC ACIDS AND BASES The data in this table are presented as values of pKa, defined as the negative logarithm of the acid dissociation constant Ka for the reaction BH 1 B– + H+ Thus pKa = –log Ka , and the hydrogen ion concentration [H+] can be calculated from [H ] [B ] + Ka = – [BH] In the case of bases, the entry in the table is for the conjugate acid; e.g., ammonium ion for ammonia. The OH– concentration in the system NH3 + H2O 1 NH4+ + OH– can be calculated from the equation [OH ] [NH ] – K b = K water / K a = [NH 3 ] 4 + where Kwater = 1.01 × 10–14 at 25 °C. Note that pKa + pKb = pKwater. All values refer to dilute aqueous solutions at zero ionic strength at the temperature indicated. The table is arranged alphabetically by compound name. REFERENCE 1. Perrin, D. D., Ionization Constants of Inorganic Acids and Bases in Aqueous Solution, Second Edition, Pergamon, Oxford, 1982. Name Formula Aluminum(III) ion Ammonia Arsenic acid Al+3 NH3 H3AsO4 Arsenious acid Barium(II) ion Boric acid H2AsO3 Ba+2 H3BO3 Calcium(II) ion Carbonic acid Ca+2 H2CO3 Chlorous acid Chromic acid HClO2 H2CrO4 Cyanic acid Germanic acid HCNO H2GeO3 Hydrazine Hydrazoic acid Hydrocyanic acid Hydrofluoric acid Hydrogen peroxide Hydrogen selenide N2H4 HN3 HCN HF H2O2 H2Se Hydrogen sulfide H2S Hydrogen telluride H2Te Hydroxylamine Hypobromous acid NH2OH HBrO Step 1 2 3 1 2 1 2 1 2 1 2 1 2 1 2 1 2 © 2000 CRC Press LLC TeamLRN t/°C 25 25 25 25 25 25 25 20 20 25 25 25 25 25 25 25 25 25 25 25 25 25 25 25 25 25 25 18 25 25 25 pKa 5.0 9.25 2.26 6.76 11.29 9.29 13.4 9.27 >14 12.6 6.35 10.33 1.94 0.74 6.49 3.46 9.01 12.3 8.1 4.6 9.21 3.20 11.62 3.89 11.0 7.05 19 2.6 11 5.94 8.55 DISSOCIATION CONSTANTS OF INORGANIC ACIDS AND BASES (continued) Name Formula Hypochlorous acid Hypoiodous acid Iodic acid Lithium ion Magnesium(II) ion Nitrous acid Perchloric acid Periodic acid Phosphoric acid HClO HIO HIO3 Li+ Mg+2 HNO2 HClO4 HIO4 H3PO4 Phosphorous acid H3PO3 Pyrophosphoric acid H4P2O7 Selenic acid Selenious acid H2SeO4 H2SeO3 Silicic acid H4SiO4 Sodium ion Strontium(II) ion Sulfamic acid Sulfuric acid Sulfurous acid Na+ Sr+2 NH2SO3H H2SO4 H2SO3 Telluric acid H2TeO4 Tellurous acid H2TeO3 Tetrafluoroboric acid Thiocyanic acid Water HBF4 HSCN H2O © 2000 CRC Press LLC Step 1 2 3 1 2 1 2 3 4 2 1 2 1 2 3 4 2 1 2 1 2 1 2 t/°C pKa 25 25 25 25 25 25 20 25 25 25 25 20 20 25 25 25 25 25 25 25 30 30 30 30 25 25 25 25 25 25 18 18 25 25 25 25 25 7.40 10.5 0.78 13.8 11.4 3.25 -1.6 1.64 2.16 7.21 12.32 1.3 6.70 0.91 2.10 6.70 9.32 1.7 2.62 8.32 9.9 11.8 12 12 14.8 13.2 1.05 1.99 1.85 7.2 7.68 11.0 6.27 8.43 0.5 -1.8 13.995 DISSOCIATION CONSTANTS OF ORGANIC ACIDS AND BASES This table lists the dissociation (ionization) constants of over 1070 organic acids, bases, and amphoteric compounds. All data apply to dilute aqueous solutions and are presented as values of pKa, which is defined as the negative of the logarithm of the equilibrium constant Ka for the reaction HA 1 H+ + Ai.e., Ka = [H+][A-]/[HA] where [H+], etc. represent the concentrations of the respective species in mol/L. It follows that pKa = pH + log[HA] - log[A-], so that a solution with 50% dissociation has pH equal to the pKa of the acid. Data for bases are presented as pKa values for the conjugate acid, i.e., for the reaction BH+ 1 H+ + B In older literature, an ionization constant Kb was used for the reaction B + H2O 1 BH+ + OH- . This is related to Ka by pKa + pKb = pKwater = 14.00 (at 25°C) Compounds are listed by molecular formula in Hill order. REFERENCES 1. Perrin, D.D., Dissociation Constants of Organic Bases in Aqueous Solution, Butterworths, London, 1965; Supplement, 1972. 2. Serjeant, E.P., and Dempsey, B., Ionization Constants of Organic Acids in Aqueous Solution, Pergamon, Oxford, 1979. 3. Albert, A., “Ionization Constants of Heterocyclic Substances”, in Katritzky, A.R., Ed., Physical Methods in Heterocyclic Chemistry, Academic Press, New York, 1963. 4. Sober, H.A., Ed., CRC Handbook of Biochemistry, CRC Press, Boca Raton, FL, 1968. 5. Perrin, D.D., Dempsey, B., and Serjeant, E.P., pKa Prediction for Organic Acids and Bases, Chapman and Hall, London, 1981. 6. Albert, A., and Serjeant, E. P., The Determination of Ionization Constants, Third Edition, Chapman and Hall, London, 1984. 7. Budavari, S., Editor, The Merck Index, Twelth Edition, Merck & Co., Whitehouse Station, NJ, 1996. Mol. Form. Name CHNO CH2N2 CH2O CH2O2 CH3NO2 CH3NS2 CH4N2O CH4N2S CH4O CH4S CH5N CH5NO CH5N3 C2HCl3O C2HCl3O2 C2HF3O2 C2H2Cl2O2 C2H2O3 C2H2O4 Cyanic acid Cyanamide Formaldehyde Formic acid Nitromethane Carbamodithioic acid Urea Thiourea Methanol Methanethiol Methylamine O-Methylhydroxylamine Guanidine Trichloroacetaldehyde Trichloroacetic acid Trifluoroacetic acid Dichloroacetic acid Glyoxylic acid Oxalic acid C2H3BrO2 C2H3ClO2 C2H3Cl3O C2H3FO2 C2H3F3O C2H3IO2 C2H3NO4 C2H3N3 C2H3N3 Bromoacetic acid Chloroacetic acid 2,2,2-Trichloroethanol Fluoroacetic acid 2,2,2-Trifluoroethanol Iodoacetic acid Nitroacetic acid 1H-1,2,3-Triazole 1H-1,2,4-Triazole Step 1 2 t/°C pKa Mol. Form. 25 29 25 25 25 25 25 25 25 25 25 3.7 1.1 13.27 3.75 10.21 2.95 0.10 -1 15.5 10.33 10.66 12.5 13.6 10.04 0.66 0.52 1.35 3.18 1.25 3.81 2.90 2.87 12.24 2.59 12.37 3.18 1.48 1.17 2.27 C2H4N2 C2H4O C2H4OS C2H4O2 C2H4O2S C2H4O3 C2H5N C2H5NO C2H5NO2 C2H5NO2 C2H5NO2 Aminoacetonitrile Acetaldehyde Thioacetic acid Acetic acid Thioglycolic acid Glycolic acid Ethyleneimine Acetamide Acetohydroxamic acid Nitroethane Glycine C2H6N2 C2H6O C2H6OS C2H6O2 C2H7AsO2 Ethanimidamide Ethanol 2-Mercaptoethanol Ethyleneglycol Dimethylarsinic acid C2H7N C2H7N C2H7NO C2H7NO3S C2H7NS Ethylamine Dimethylamine Ethanolamine 2-Aminoethanesulfonic acid Cysteamine C2H7N5 Biguanide C2H8N2 1,2-Ethanediamine 25 25 20 25 25 25 25 25 25 25 25 25 25 25 24 20 20 TeamLRN Name Step t/°C 25 25 25 25 25 25 25 25 1 2 1 2 1 2 1 2 1 2 1 2 25 25 25 25 25 25 25 25 25 25 25 25 25 25 25 25 25 25 pKa 5.34 13.57 3.33 4.756 3.68 3.83 8.04 15.1 8.70 8.46 2.35 9.78 12.1 15.5 9.72 15.1 1.57 6.27 10.65 10.73 9.50 1.5 9.06 8.27 10.53 11.52 2.93 9.92 6.86 DISSOCIATION CONSTANTS OF ORGANIC ACIDS AND BASES (continued) Mol. Form. C2H8O7P2 C3H2O2 C3H3NO C3H3NO C3H3NO2 C3H3NS C3H3N3O3 Name 1-Hydroxy-1,1diphosphonoethane 2-Propynoic acid Oxazole Isoxazole Cyanoacetic acid Thiazole Cyanuric acid C3H4N2 C3H4N2 C3H4N2S C3H4O C3H4O2 C3H4O3 C3H4O4 1H-Pyrazole Imidazole 2-Thiazolamine Propargyl alcohol Acrylic acid Pyruvic acid Malonic acid C3H4O5 C3H6O C3H6O2 C3H6O2S C3H6O3 C3H6O3 C3H6O4 C3H7N C3H7N C3H7NO C3H7NO2 Hydroxypropanedioic acid 3-Bromopropanoic acid 2-Chloropropanoic acid 3-Chloropropanoic acid 3-Aminopropanenitrile 1,3,5-Triazine-2,4,6triamine Allyl alcohol Propanoic acid (Methylthio)acetic acid Lactic acid 3-Hydroxypropanoic acid Glyceric acid Allylamine Azetidine 2-Propanone oxime L-Alanine C3H7NO2 β-Alanine C3H7NO2 Sarcosine C3H7NO2S L-Cysteine C3H5BrO2 C3H5ClO2 C3H5ClO2 C3H6N2 C3H6N6 C3H7NO3 L-Serine C3H7NO5S DL-Cysteic acid C3H7N3O2 C3H8O2 Glycocyamine Ethylene glycol monomethyl ether Glycerol Propylamine Isopropylamine Trimethylamine C3H8O3 C3H9N C3H9N C3H9N Step t/°C 1 2 1 2 1 2 1 2 25 20 25 25 25 25 20 20 20 20 9.40 4.65 9.82 6.61 10.55 8.88 9.69 7.93 9.59 7.95 3.26 0.65 1.23 2.24 9.45 4.01 6.64 0.35 2.62 1.92 6.23 3.02 4.38 2.55 4.37 13.03 -3.8 9.62 3.45 5.71 4.60 12.16 7.6 C3H9NO C3H9NO C3H10N2 2-Methoxyethylamine Trimethylamine oxide 1,2-Propanediamine, (±) C3H10N2 1,3-Propanediamine C3H10N2O 1,3-Diamino-2-propanol C3H11N3 1,2,3-Triaminopropane C4H4FN3O C4H4N2 C4H4N2 C4H4N2 C4H4N2O2 C4H4N2O3 C4H4N2O5 C4H4N4O2 C4H4O2 C4H4O4 Flucytosine Pyrazine Pyrimidine Pyridazine Uracil Barbituric acid Alloxanic acid 5-Nitropyrimidinamine 2-Butynoic acid Maleic acid C4H4O4 Fumaric acid 25 25 25 20 25 C4H4O5 Oxaloacetic acid 25 25 25 25 25 25 25 25 25 25 25 25 25 25 25 25 25 25 25 25 25 25 25 25 25 15.5 4.87 3.66 3.86 4.51 3.52 9.49 11.29 12.42 2.34 9.87 3.55 10.24 2.21 10.1 1.5 8.7 10.2 2.19 9.21 1.3 1.9 8.70 2.82 14.8 C4H5N C4H5NO2 C4H5N3 C4H5N3 C4H5N3O Pyrrole Succinimide 2-Pyrimidinamine 4-Pyrimidinamine Cytosine C4H5N3O2 25 25 25 25 14.15 10.54 10.63 9.80 6-Methyl-1,2,4-triazine3,5(2H,4H)-dione 1-Methylimidazol Allantoin Acetazolamide trans-Crotonic acid 3-Butenoic acid Cyclopropanecarboxylic acid 2-Oxobutanoic acid Acetoacetic acid Succinic acid 1 2 Methylmalonic acid 1 2 Malic acid 1 2 DL-Tartaric acid 1 2 meso-Tartaric acid 1 2 L-Tartaric acid 1 2 Dihydroxytartaric acid 2-Chlorobutanoic acid 3-Chlorobutanoic acid 4-Chlorobutanoic acid 1 2 3 1 2 1 2 1 2 1 2 3 1 2 1 2 3 pKa 1.35 2.87 7.03 11.3 1.84 0.8 -2.0 2.47 2.52 6.88 11.40 13.5 2.49 6.99 5.36 13.6 4.25 2.39 2.85 5.70 2.42 4.54 4.00 2.83 3.98 7.80 5.00 25 33 25 25 25 1 2 1 2 t/°C Mol. Form. 1 2 3 4 25 25 20 25 25 25 25 25 C4H6N2 C4H6N4O3 C4H6N4O3S2 C4H6O2 C4H6O2 C4H6O2 C4H6O3 C4H6O3 C4H6O4 C4H6O4 C4H6O5 C4H6O6 C4H6O6 C4H6O6 C4H6O8 C4H7ClO2 C4H7ClO2 C4H7ClO2 Name Step pKa 1 2 1 2 1 2 3 20 20 20 25 25 25 20 25 25 25 25 25 25 25 25 25 25 20 20 1 2 25 25 25 25 25 25 25 25 25 25 25 25 25 25 25 25 25 25 25 25 6.95 8.96 7.2 4.69 4.34 4.83 2.50 3.6 4.21 5.64 3.07 5.76 3.40 5.11 3.03 4.37 3.17 4.91 2.98 4.34 1.92 2.86 4.05 4.52 DISSOCIATION CONSTANTS OF ORGANIC ACIDS AND BASES (continued) Mol. Form. Name C4H7NO2 C4H7NO3 C4H7NO4 4-Cyanobutanoic acid N-Acetylglycine Iminodiacetic acid C4H7NO4 L-Aspartic acid Step 1 2 1 2 3 1 2 C4H7N3O Creatinine C4H7N5 C4H8N2O3 2,4,6-Pyrimidinetriamine L-Asparagine C4H8N2O3 N-Glycylglycine C4H8O2 C4H8O2 C4H8O3 C4H8O3 C4H8O3 C4H9N C4H9NO C4H9NO2 Butanoic acid 2-Methylpropanoic acid 3-Hydroxybutanoic acid, (±) 4-Hydroxybutanoic acid Ethoxyacetic acid Pyrrolidine Morpholine 2-Methylalanine 1 2 N,N-Dimethylglycine DL-2-Aminobutanoic acid 1 2 4-Aminobutanoic acid 1 2 DL-Homocysteine 1 2 3 L-Threonine 1 2 L-Homoserine 1 2 Creatine 1 2 Piperazine 1 2 2,4-Diaminobutanoic acid 1 2 3 1,2,3,4-Butanetetrol Butylamine sec-Butylamine tert-Butylamine Diethylamine Tris(hydroxymethyl) methylamine 1,4-Butanediamine 1 2 3-Bromopyridine 2-Chloropyridine 3-Chloropyridine 4-Chloropyridine 2-Fluoropyridine 4-Nitropyridine 1H-Purine 1 2 C4H9NO2 C4H9NO2 C4H9NO2 C4H9NO2S C4H9NO3 C4H9NO3 C4H9N3O2 C4H10N2 C4H10N2O2 C4H10O4 C4H11N C4H11N C4H11N C4H11N C4H11NO3 C4H12N2 C5H4BrN C5H4ClN C5H4ClN C5H4ClN C5H4FN C5H4N2O2 C5H4N4 1 2 1 2 t/°C pKa Mol. Form. 25 25 C5H4N4O C5H4N4O C5H4N4O3 C5H4N4S 25 25 25 25 20 2.42 3.67 2.98 9.89 1.99 3.90 9.90 4.8 9.2 6.84 2.1 8.80 3.14 8.17 4.83 4.84 4.70 4.72 3.65 11.31 8.50 2.36 10.21 9.89 2.29 9.83 4.031 10.556 2.22 8.87 10.86 2.09 9.10 2.71 9.62 2.63 14.3 9.73 5.33 1.85 8.24 10.44 13.9 10.60 10.56 10.68 10.84 8.3 25 25 25 25 25 25 25 25 20 20 10.80 9.63 2.84 0.49 2.81 3.83 -0.44 1.61 2.30 8.96 25 25 25 25 20 20 20 25 25 20 25 25 18 25 25 25 25 25 25 25 25 25 25 25 25 25 25 25 25 25 25 25 25 25 25 25 C5H4O2S C5H4O2S C5H4O3 C5H4O3 C5H5N C5H5NO C5H5NO C5H5NO C5H5NO C5H5NO C5H5NO2 C5H5NO2 C5H5N3O C5H5N5 C5H5N5O C5H6N2 C5H6N2 C5H6N2 C5H6N2 C5H6N2O2 C5H6O4 C5H6O4 C5H6O4 C5H6O5 C5H7NO3 C5H7NO3 C5H7N3 C5H7N3 C5H7N3O4 C5H8N2 C5H8N4O3S2 C5H8O2 C5H8O4 C5H8O4 C5H8O4 C5H9NO2 C5H9NO3 C5H9NO3 TeamLRN Name Step Hypoxanthine Allopurinol Uric acid 1,7-Dihydro-6H1 purine-6-thione 2 2-Thiophenecarboxylic acid 3-Thiophenecarboxylic acid 2-Furancarboxylic acid 3-Furancarboxylic acid Pyridine 2-Pyridinol 1 2 3-Pyridinol 1 2 4-Pyridinol 1 2 2(1H)-Pyridinone 1 2 Pyridine-1-oxide 1H-Pyrrole-2-carboxylic acid 1H-Pyrrole-3-carboxylic acid Pyrazinecarboxamide Adenine 1 2 Guanine 2-Pyridinamine 3-Pyridinamine 4-Pyridinamine 2-Methylpyrazine Thymine 1,1-Cyclopropanedi1 carboxylic acid 2 trans-1-Propene-1,21 dicarboxylic acid 2 1-Propene-2,31 dicarboxylic acid 2 2-Oxoglutaric acid 1 2 5,5-Dimethyl-2,4oxazolidinedione L-Pyroglutamic acid 2,5-Pyridinediamine Methylaminopyrazine Azaserine 2,4-Dimethylimidazole Methazolamide trans-3-Pentenoic acid Dimethylmalonic acid Glutaric acid 1 2 Methylsuccinic acid 1 2 L-Proline 1 2 5-Amino-4-oxopentanoic 1 acid 2 trans-4-Hydroxyproline 1 t/°C pKa 25 25 25 25 25 25 20 20 20 20 20 20 20 20 24 20 8.7 10.2 3.89 7.77 11.17 3.49 4.1 3.16 3.9 5.23 0.75 11.65 4.79 8.75 3.20 11.12 0.75 11.65 0.79 4.45 20 5.00 40 20 25 25 27 25 25 25 25 25 25 25 25 25 37 0.5 4.3 9.83 9.92 6.82 6.04 9.11 1.45 9.94 1.82 7.43 3.09 4.75 3.85 5.45 2.47 4.68 6.13 12 25 20 25 25 25 25 18 25 25 25 25 25 25 25 25 3.32 6.48 3.39 8.55 8.36 7.30 4.51 3.15 4.32 5.42 4.13 5.64 1.95 10.64 4.05 8.90 1.82 DISSOCIATION CONSTANTS OF ORGANIC ACIDS AND BASES (continued) Mol. Form. Name Step t/°C pKa Mol. Form. 2 1 2 3 1 2 25 25 25 9.66 2.13 4.31 9.67 6.04 9.75 3.15 2.17 9.13 2.98 8.38 4.83 4.80 4.77 5.03 12.61 12.22 12.14 11.123 10.46 7.38 2.29 9.74 2.36 9.72 2.32 9.81 2.35 10.19 4.27 10.77 1.83 2.13 9.27 2 1.71 8.69 10.76 10.63 10.59 10.60 10.85 10.15 10.35 13.9 10.05 10.93 3.6 C6H5ClO C6H5ClO C6H5ClO C6H5Cl2N C6H5FO C6H5FO C6H5FO C6H5IO C6H5IO C6H5IO C6H5NO C6H5NO C6H5NO2 C6H5NO2 C5H9NO4 L-Glutamic acid C5H9N3 Histamine C5H10N2O3 C5H10N2O3 Glycylalanine L-Glutamine C5H10N2O4 Glycylserine C5H10O2 C5H10O2 C5H10O2 C5H10O2 C5H10O4 C5H10O5 C5H10O5 C5H11N C5H11N C5H11NO C5H11NO2 Pentanoic acid 2-Methylbutanoic acid 3-Methylbutanoic acid 2,2-Dimethylpropanoic acid D-2-Deoxyribose L-Ribose D-Xylose Piperidine N-Methylpyrrolidine 4-Methylmorpholine L-Valine 1 2 DL-Norvaline 1 2 L-Norvaline 1 2 N-Propylglycine 1 2 5-Aminopentanoic acid 1 2 Betaine L-Methionine 1 2 Tetramethylurea L-Ornithine 1 2 3 Pentylamine 3-Pentanamine 3-Methyl-1-butanamine 2-Methyl-2-butanamine 2,2-Dimethylpropylamine Diethylmethylamine Choline 1,5-Pentanediamine 1 2 4-Amino-3,5,6-trichloro2-pyridinecarboxlic acid 2,4,6-Trinitrophenol 2,3-Dichlorophenol 2,4-Dinitrophenol 2,5-Dinitrophenol Pteridine 2-Bromophenol 3-Bromophenol 4-Bromophenol 3,5-Dibromoaniline C5H11NO2 C5H11NO2 C5H11NO2 C5H11NO2 C5H11NO2 C5H11NO2S C5H12N2O C5H12N2O2 C5H13N C5H13N C5H13N C5H13N C5H13N C5H13N C5H14NO C5H14N2 C6H3Cl3N2O2 C6H3N3O7 C6H4Cl2O C6H4N2O5 C6H4N2O5 C6H4N4 C6H5BrO C6H5BrO C6H5BrO C6H5Br2N 1 2 1 2 25 25 25 25 25 25 25 20 25 25 20 25 25 18 25 25 25 25 25 25 25 25 25 25 25 0 25 25 25 25 25 25 17 25 19 25 25 25 25 25 C6H5NO2 C6H5NO2 C6H5NO3 C6H5NO3 C6H5NO3 C6H5N3 C6H5N5O C6H5N5O2 C6H6BrN C6H6BrN C6H6BrN C6H6ClN C6H6ClN C6H6ClN C6H6FN C6H6FN C6H6FN C6H6IN C6H6IN C6H6IN C6H6N2O C6H6N2O C6H6N2O2 C6H6N2O2 C6H6N2O2 C6H6O C6H6O2 C6H6O2 24 25 25 15 20 25 25 25 25 0.42 7.44 4.07 5.15 4.05 8.45 9.03 9.37 2.34 C6H6O2 C6H6O2S C6H6O3S C6H6O4 C6H6O4S Name Step 2-Chlorophenol 3-Chlorophenol 4-Chlorophenol 2,4-Dichloroaniline 2-Fluorophenol 3-Fluorophenol 4-Fluorophenol 2-Iodophenol 3-Iodophenol 4-Iodophenol 2-Pyridinecarboxaldehyde 4-Pyridinecarboxaldehyde Nitrobenzene 2-Pyridinecarboxylic acid 1 2 3-Pyridinecarboxylic acid 1 2 4-Pyridinecarboxylic acid 1 2 2-Nitrophenol 3-Nitrophenol 4-Nitrophenol 1H-Benzotriazole 2-Amino-41 hydroxypteridine 2 Xanthopterin 2 3 2-Bromoaniline 3-Bromoaniline 4-Bromoaniline 2-Chloroaniline 3-Chloroaniline 4-Chloroaniline 2-Fluoroaniline 3-Fluoroaniline 4-Fluoroaniline 2-Iodoaniline 3-Iodoaniline 4-Iodoaniline 3-Pyridinecarboxamide 2-Pyridinecarbox1 aldehyde oxime 2 2-Nitroaniline 3-Nitroaniline 4-Nitroaniline Phenol p-Hydroquinone 1 2 Pyrocatechol 1 2 Resorcinol 1 2 Benzenesulfinic acid Benzenesulfonic acid 5-Hydroxy-2-(hydroxymethyl)-4H-pyran-4-one 3-Hydroxybenzenesulfonic acid t/°C pKa 25 25 25 22 25 25 25 25 25 25 25 30 0 20 20 25 25 25 25 25 25 25 20 20 20 20 20 25 25 25 25 25 25 25 25 25 25 25 25 20 20 20 25 25 25 25 25 25 25 25 25 25 20 25 8.56 9.12 9.41 2.05 8.73 9.29 9.89 8.51 9.03 9.33 12.68 12.05 3.98 0.99 5.39 2.00 4.82 1.77 4.84 7.23 8.36 7.15 1.6 2.27 7.96 6.59 9.31 2.53 3.53 3.89 2.66 3.52 3.98 3.20 3.59 4.65 2.54 3.58 3.81 3.3 3.59 10.18 -0.25 2.46 1.02 9.99 9.85 11.4 9.34 12.6 9.32 11.1 1.3 0.70 7.9 25 9.07 DISSOCIATION CONSTANTS OF ORGANIC ACIDS AND BASES (continued) Mol. Form. C6H6O4S Name C6H6S C6H7BO2 C6H7N C6H7N C6H7N C6H7N C6H7NO 4-Hydroxybenzenesulfonic acid cis-1-Propene-1,2,3tricarboxylic acid trans-1-Propene-1,2,3tricarboxylic acid Benzenethiol Benzeneboronic acid Aniline 2-Methylpyridine 3-Methylpyridine 4-Methylpyridine 2-Aminophenol C6H7NO 3-Aminophenol C6H7NO 4-Aminophenol C6H7NO C6H7NO C6H7NO C6H7NO3S C6H8N2 C6H8N2 2-Methoxypyridine 3-Methoxypyridine 4-Methoxypyridine 2-Aminobenzenesulfonic acid 3-Aminobenzenesulfonic acid 4-Aminobenzenesulfonic acid N-Methylpyridinamine o-Phenylenediamine C6H8N2 m-Phenylenediamine C6H8N2 p-Phenylenediamine C6H8N2 C6H8O2 C6H8O2 C6H8O4 Phenylhydrazine 2,4-Hexadienoic acid 1,3-Cyclohexanedione 2,2-Dimethyl-1,3dioxane-4,6-dione L-Ascorbic acid C6H6O6 C6H6O6 C6H7NO3S C6H7NO3S C6H8O6 C6H8O7 C6H8O7 C6H9NO6 C6H9NO6 C6H9N3 C6H9N3O2 Step 1 2 1 2 1 2 1 2 1 2 1 2 1 2 1 2 Citric acid 1 2 3 Isocitric acid 1 2 3 Nitrilotriacetic acid 1 2 3 L-γ-Carboxyglutamic acid 1 2 3 4 4,6-Dimethylpyrimidinamine L-Histidine 1 2 3 t/°C pKa Mol. Form. 25 9.11 C6H10O2 25 1.95 25 25 25 25 25 25 25 20 20 20 20 25 25 20 25 25 25 2.80 4.46 6.62 8.83 4.87 6.00 5.70 5.99 4.78 9.97 4.37 9.82 5.48 10.30 3.28 4.78 6.58 2.46 C6H10O3 C6H10O4 C6H10O4 25 3.74 25 3.23 20 20 20 20 20 20 20 15 25 25 9.65 4.57 0.80 5.11 2.50 6.31 2.97 8.79 4.76 5.26 5.1 25 16 25 25 25 25 25 25 20 20 20 25 25 25 25 20 4.04 11.7 3.13 4.76 6.40 3.29 4.71 6.40 3.03 3.07 10.70 1.7 3.2 4.75 9.9 4.82 25 25 25 1.80 6.04 9.33 C6H11NO2 C6H11NO3 C6H11NO4 C6H11N3O4 C6H11N3O4 C6H12N2 C6H12N2O4S2 C6H12O2 C6H12O2 C6H12O6 C6H12O6 C6H12O6 C6H13N C6H13N C6H13N C6H13NO C6H13NO2 C6H13NO2 C6H13NO2 C6H13NO2 C6H13NO4 C6H13N3O3 C6H14N2 C6H14N2 C6H14N2 C6H14N2O2 C6H14N4O2 C6H14O6 C6H15N C6H15N C6H15N TeamLRN Name Cyclopentanecarboxylic acid Ethyl acetoacetate 3-Methylglutaric acid Adipic acid 2-Piperidinecarboxylic acid Adipamic acid 2-Aminoadipic acid Step 1 2 1 2 1 2 3 N-(N-Glycylglycyl)glycine 1 2 Glycylasparagine 1 2 Triethylenediamine 1 2 L-Cystine 1 2 3 4 Hexanoic acid 4-Methylpentanoic acid β-D-Fructose α-D-Glucose D-Mannose Cyclohexylamine 1-Methylpiperidine 1,2-Dimethylpyrrolidine N-Ethylmorpholine L-Leucine 1 2 L-Isoleucine 1 2 L-Norleucine 1 2 6-Aminohexanoic acid 1 2 N,N-Bis(2-hydroxy2 ethyl)glycine Citrulline 1 2 cis-1,2-Cyclohexane1 diamine 2 trans-1,2-Cyclohexane1 diamine 2 cis-2,5-Dimethyl1 piperazine 2 L-Lysine 1 2 3 L-Arginine 1 2 3 D-Mannitol Hexylamine Diisopropylamine Triethylamine t/°C pKa 25 4.99 25 25 18 18 25 25 25 25 25 25 25 25 25 18 25 18 25 25 25 25 25 26 25 25 25 25 25 25 25 25 25 20 10.68 4.24 4.41 5.41 2.28 10.72 4.63 2.14 4.21 9.77 3.225 8.09 2.942 8.44 3.0 8.7 1 2.1 8.02 8.71 4.85 4.84 12.27 12.46 12.08 10.64 10.38 10.20 7.67 2.33 9.74 2.32 9.76 2.34 9.83 4.37 10.80 8.35 25 25 20 20 20 20 25 25 25 25 25 25 25 25 18 25 25 25 2.43 9.69 9.93 6.13 9.94 6.47 9.66 5.20 2.16 9.06 10.54 1.82 8.99 12.5 13.5 10.56 11.05 10.75 DISSOCIATION CONSTANTS OF ORGANIC ACIDS AND BASES (continued) Mol. Form. C6H15NO3 C6H16N2 C6H16N2 Name Triethanolamine 1,6-Hexanediamine N,N,N’,N’-Tetramethyl1,2-ethanediamine C6H19NSi2 Hexamethyldisilazane Pentafluorobenzoic acid C7HF5O2 C7H3Br2NO 3,5-Dibromo-4hydroxybenzonitrile C7H3N3O8 2,4,6-Trinitrobenzoic acid C7H4Cl3NO3 Triclopyr C7H4N2O6 2,4-Dinitrobenzoic acid 2-Bromobenzoic acid C7H5BrO2 C7H5BrO2 3-Bromobenzoic acid C7H5BrO2 4-Bromobenzoic acid 2-Chlorobenzoic acid C7H5ClO2 C7H5ClO2 3-Chlorobenzoic acid C7H5ClO2 4-Chlorobenzoic acid 2-Fluorobenzoic acid C7H5FO2 C7H5FO2 3-Fluorobenzoic acid C7H5FO2 4-Fluorobenzoic acid C7H5F3O 2-(Trifluoromethyl)phenol C7H5F3O 3-(Trifluoromethyl)phenol C7H5IO2 2-Iodobenzoic acid C7H5IO2 3-Iodobenzoic acid C7H5IO2 4-Iodobenzoic acid C7H5NO 2-Hydroxybenzonitrile C7H5NO 3-Hydroxybenzonitrile C7H5NO 4-Hydroxybenzonitrile C7H5NO3S Saccharin C7H5NO4 2-Nitrobenzoic acid C7H5NO4 3-Nitrobenzoic acid C7H5NO4 4-Nitrobenzoic acid C7H5NO4 2,3-Pyridinedicarboxylic acid C7H5NO4 2,4-Pyridinedicarboxylic acid C7H5NO4 2,6-Pyridinedicarboxylic acid C7H5NO4 3,5-Pyridinedicarboxylic acid C7H6ClN3O4S2 Chlorothiazide C7H6F3N C7H6F3N C7H6N2 C7H6N2 C7H6N2 C7H6N2 C7H6O C7H6O2 C7H6O2 C7H6O2 C7H6O2 C7H6O3 C7H6O3 C7H6O3 Step t/°C pKa 1 2 1 2 25 0 0 25 25 7.76 11.86 10.76 10.40 8.26 7.55 1.75 4.06 25 25 1 2 1 25 25 25 25 25 25 25 25 25 25 25 25 25 25 25 25 25 25 18 25 25 25 25 25 25 0.65 2.68 1.43 2.85 3.81 3.96 2.90 3.84 4.00 3.27 3.86 4.15 8.95 8.68 2.86 3.87 4.00 6.86 8.61 7.97 11.68 2.17 3.46 3.43 2.43 4.78 2.15 1 2 1 25 25 25 2.16 4.76 2.80 25 25 25 25 25 25 25 25 25 25 25 20 20 25 19 25 6.85 9.45 3.49 2.45 5.53 0.77 2.75 1.74 14.90 4.204 8.37 8.98 7.61 2.98 13.6 4.08 9.92 4.57 1 2 3-(Trifluoromethyl)aniline 4-(Trifluoromethyl)aniline 1H-Benzimidazole 2-Aminobenzonitrile 3-Aminobenzonitrile 4-Aminobenzonitrile Benzaldehyde Benzoic acid Salicylaldehyde 3-Hydroxybenzaldehyde 4-Hydroxybenzaldehyde 2-Hydroxybenzoic acid 1 2 3-Hydroxybenzoic acid 1 2 4-Hydroxybenzoic acid 1 Mol. Form. Name Step 2 2,4-Dihydroxybenzoic acid 1 2 3 C7H6O4 2,5-Dihydroxybenzoic acid 1 C7H6O4 3,4-Dihydroxybenzoic acid 1 2 3 C7H6O4 3,5-Dihydroxybenzoic acid 1 2,4,6-Trihydroxybenzoic C7H6O5 acid C7H6O5 3,4,5-Trihydroxybenzoic acid C7H7NO Benzamide C7H7NO2 Aniline-2-carboxylic acid 1 2 C7H7NO2 Aniline-3-carboxylic acid 1 2 C7H7NO2 Aniline-4-carboxylic acid 1 2 C7H7NO3 4-Amino-2-hydroxybenzoic acid 1 C7H8ClN3O4S2 Hydrochlorothiazide 2 C7H8N4O2 Theobromine C7H8N4O2 Theophylline 1 C7H8O o-Cresol C7H8O m-Cresol C7H8O p-Cresol C7H8OS 4-(Methylthio)phenol C7H8O2 2-Methoxyphenol C7H8O2 3-Methoxyphenol C7H8O2 4-Methoxyphenol C7H8S Benzenemethanethiol C7H9N Benzylamine C7H9N 2-Methylaniline C7H9N 3-Methylaniline C7H9N 4-Methylaniline C7H9N N-Methylaniline C7H9N 2-Ethylpyridine C7H9N 2,3-Dimethylpyridine C7H9N 2,4-Dimethylpyridine C7H9N 2,5-Dimethylpyridine C7H9N 2,6-Dimethylpyridine C7H9N 3,4-Dimethylpyridine 3,5-Dimethylpyridine C7H9N C7H9NO 2-Methoxyaniline C7H9NO 3-Methoxyaniline C7H9NO 4-Methoxyaniline C7H9NS 2-(Methylthio)aniline C7H9NS 4-(Methylthio)aniline C7H9N5 2-Dimethylaminopurine 1 2 C7H11N3O2 L-1-Methylhistidine 1 2 3 C7H11N3O2 L-3-Methylhistidine 1 2 3 C7H6O4 t/°C pKa 25 25 25 25 25 25 25 25 25 25 9.46 3.11 8.55 14.0 2.97 4.48 8.83 12.6 4.04 1.68 25 4.41 25 25 25 25 25 25 25 ˜13 2.17 4.85 3.07 4.79 2.50 4.87 3.25 18 25 25 25 25 25 25 25 25 25 25 25 25 25 25 25 25 25 25 25 25 25 25 25 25 25 25 20 20 25 25 25 25 25 25 7.9 9.2 7.89 8.77 10.29 10.09 10.26 9.53 9.98 9.65 10.21 9.43 9.34 4.45 4.71 5.08 4.85 5.89 6.57 6.99 6.40 6.65 6.46 6.15 4.53 4.20 5.36 3.45 4.35 4.00 10.24 1.69 6.48 8.85 1.92 6.56 8.73 DISSOCIATION CONSTANTS OF ORGANIC ACIDS AND BASES (continued) Mol. Form. C7H12O2 C7H12O4 Name Step Cyclohexanecarboxylic acid Heptanedioic acid 1 2 C7H12O4 Butylpropanedioic acid 1 C7H13NO4 α-Ethylglutamic acid 1 2 C7H14O2 Heptanoic acid C7H14O6 α-Methylglucoside C7H15N 1-Ethylpiperidine 1,2-Dimethylpiperidine,(±) C7H15N C7H15NO3 Carnitine C7H17N Heptylamine 2-Heptanamine C7H17N C8H5NO2 3-Cyanobenzoic acid C8H5NO2 4-Cyanobenzoic acid Cinnoline C8H6N2 C8H6N2 Quinazoline C8H6N2 Quinoxaline Phthalazine C8H6N2 C8H6N4O5 Nitrofurantoin C8H6O3 3-Formylbenzoic acid C8H6O3 4-Formylbenzoic acid C8H6O4 Phthalic acid 1 2 C8H6O4 Isophthalic acid 1 2 Terephthalic acid 1 C8H6O4 2 C8H7ClO2 2-Chlorobenzeneacetic acid C8H7ClO2 3-Chlorobenzeneacetic acid C8H7ClO2 4-Chlorobenzeneacetic acid C8H7ClO3 2-Chlorophenoxyacetic acid C8H7ClO3 3-Chlorophenoxyacetic acid C8H7NO4 2-Nitrobenzeneacetic acid C8H7NO4 3-Nitrobenzeneacetic acid C8H7NO4 4-Nitrobenzeneacetic acid C8H8F3N3O4S2 Hydroflumethiazide 1 2 C8H8N2 2-Methyl-1H-benzimidazole C8H8O2 o-Toluic acid C8H8O2 m-Toluic acid C8H8O2 p-Toluic acid C8H8O2 Benzeneacetic acid C8H8O2 1-(2-Hydroxyphenyl)ethanone C8H8O2 1-(3-Hydroxyphenyl)ethanone C8H8O2 1-(4-Hydroxyphenyl)ethanone C8H8O3 2-Methoxybenzoic acid C8H8O3 3-Methoxybenzoic acid C8H8O3 4-Methoxybenzoic acid C8H8O3 Phenoxyacetic acid C8H8O3 Mandelic acid C8H8O4 2,5-Hydroxybenzeneacetic acid C8H9NO Acetanilide C8H9NO2 2-(Methylamino)benzoic acid C8H9NO2 3-(Methylamino)benzoic acid t/°C pKa Mol. Form. 25 25 25 5 25 25 25 25 23 25 25 25 19 25 25 20 29 20 20 C8H9NO2 25 25 25 25 25 25 25 25 25 25 25 25 25 25 4.91 4.71 5.58 2.96 3.846 7.838 4.89 13.71 10.45 10.22 3.80 10.67 10.7 3.60 3.55 2.37 3.43 0.56 3.47 7.2 3.84 3.77 2.943 5.432 3.70 4.60 3.54 4.34 4.07 4.14 4.19 3.05 3.10 4.00 3.97 3.85 8.9 9.7 6.19 3.91 4.25 4.37 4.31 10.06 9.19 8.05 4.08 4.10 4.50 3.17 3.37 4.40 25 25 0.5 5.34 25 5.10 25 25 25 25 25 25 25 25 25 25 25 25 25 25 25 25 C8H9NO2 C8H10BrN C8H10ClN C8H10ClN C8H10N2O2 C8H11N C8H11N C8H11N C8H11N C8H11N C8H11NO C8H11NO C8H11NO C8H11NO C8H11NO C8H11NO2 C8H11NO3 C8H11N3O6 C8H11N5 C8H12N2O3 C8H12O2 C8H13NO2 C8H14O2S2 C8H14O4 C8H15NO C8H15NO C8H16N2O3 C8H16N2O3 C8H16N2O4S2 C8H16O2 C8H16O2 C8H17N C8H17N C8H17NO C8H19N C8H19N C8H19N C8H20N2 C9H6BrN C9H7ClO2 TeamLRN Name 4-(Methylamino)benzoic acid N-Phenylglycine 4-Bromo-N,Ndimethylaniline 3-Chloro-N,Ndimethylaniline 4-Chloro-N,Ndimethylaniline N,N-Dimethyl-3nitroaniline N-Ethylaniline N,N-Dimethylaniline 2,6-Dimethylaniline Benzeneethanamine 2,4,6-Trimethylpyridine 2-Ethoxyaniline 3-Ethoxyaniline 4-Ethoxyaniline 4-(2-Aminoethyl)phenol Step 1 2 1 2 2-(2-Methoxyethyl)pyridine Dopamine 1 2 Norepinephrine 1 2 6-Azauridine Phenylbiguanide 1 2 Barbital 5,5-Dimethyl-1,3cyclohexanedione Arecoline Thioctic acid Octanedioic acid 1 Tropine Pseudotropine N-Glycylleucine N-Leucylglycine 1 2 Homocystine 1 2 3 4 Octanoic acid 2-Propylpentanoic acid 2-Propylpiperidine,(S) 2,2,4-Trimethylpiperidine trans-6-Propyl-3piperidinol,(3S) Octylamine N-Methyl-2-heptanamine Dibutylamine 1,8-Octanediamine 1 2 3-Bromoquinoline trans-o-Chlorocinnamic acid t/°C pKa 25 5.04 25 25 1.83 4.39 4.23 20 3.83 20 4.39 25 2.62 25 25 25 25 25 28 25 28 25 25 5.12 5.07 3.89 9.83 7.43 4.43 4.18 5.20 9.74 10.52 5.5 8.9 10.6 8.64 9.70 6.70 10.76 2.13 7.43 5.15 25 25 25 25 25 25 25 15 15 25 25 25 25 25 25 25 25 30 25 17 21 20 20 25 25 6.84 5.4 4.52 3.80 3.80 3.18 3.25 8.2 1.59 2.54 8.52 9.44 4.89 4.6 10.9 11.04 10.3 10.65 10.99 11.25 11.00 10.1 2.69 4.23 DISSOCIATION CONSTANTS OF ORGANIC ACIDS AND BASES (continued) Mol. Form. C9H7ClO2 Name Step C9H7N C9H7N C9H7NO trans-m-Chlorocinnamic acid trans-p-Chlorocinnamic acid Quinoline Isoquinoline 2-Quinolinol C9H7NO 3-Quinolinol C9H7NO 4-Quinolinol C9H7NO 6-Quinolinol C9H7NO 8-Quinolinol C9H7NO 7-Isoquinolinol C9H7NO3 C9H7NO3 C9H7NO3 C9H7N7O2S C9H8N2 C9H8N2 C9H8N2 C9H8N2 C9H8N2 C9H8O2 C9H8O2 C9H8O2 2-Cyanophenoxyacetic acid 3-Cyanophenoxyacetic acid 4-Cyanophenoxyacetic acid Azathioprine 2-Quinolinamine 3-Quinolinamine 4-Quinolinamine 1-Isoquinolinamine 3-Isoquinolinamine cis-Cinnamic acid trans-Cinnamic acid α-Methylenebenezeneacetic acid 2-(Acetyloxy)benzoic acid 3,5-Dibromo-L-tyrosine 1 2 3 3-(2-Chlorophenyl)propanoic acid 3-(3-Chlorophenyl)propanoic acid 3-(4-Chlorophenyl)propanoic acid L-3,5-Diiodotyrosine 1 2 3 N-Benzoylglycine 3-(2-Nitrophenyl)propanoic acid 3-(4-Nitrophenyl)propanoic acid Carbendazim Sulfathiazole L-3-Iodotyrosine 1 2 3 2-Ethylbenzimidazole 3,5-Dimethylbenzoic acid Benzenepropanoic acid α-Methylbenzeneacetic acid α-Hydroxy-α-methylbenezeneacetic acid C9H7ClO2 C9H8O4 C9H9Br2NO3 C9H9ClO2 C9H9ClO2 C9H9ClO2 C9H9I2NO3 C9H9NO3 C9H9NO4 C9H9NO4 C9H9N3O2 C9H9N3O2S2 C9H10INO3 C9H10N2 C9H10O2 C9H10O2 C9H10O2 C9H10O3 t/°C 25 1 2 1 2 1 2 1 2 1 2 1 2 pKa 4.29 25 4.41 20 20 20 20 20 20 20 20 20 20 25 25 20 20 25 25 25 4.90 5.40 -0.31 11.76 4.28 8.08 2.23 11.28 5.15 8.90 4.91 9.81 5.68 8.90 2.98 3.03 2.93 8.2 7.34 4.91 9.17 7.62 5.05 3.88 4.44 4.35 20 20 20 20 20 25 25 25 25 3.48 2.17 6.45 7.60 4.58 25 4.59 25 4.61 25 25 25 25 25 2.12 5.32 9.48 3.62 4.50 25 4.47 25 25 25 25 25 25 25 25 4.48 7.2 2.2 8.7 9.1 6.18 4.32 4.66 4.64 3.47 Mol. Form. Name C9H11Cl2N3O4S2 Methylclothiazide C9H11N N-Allylaniline C9H11N 1-Indanamine 4-(Dimethylamino)C9H11NO2 benzoic acid C9H11NO2 Ethyl 4-aminobenzoate L-Phenylalanine C9H11NO2 Step 25 22 1 2 1 2 1 2 3 1 2 3 4 C9H11NO3 L-Tyrosine C9H11NO4 Levodopa C9H12N2O2 C9H13N C9H13NO3 Tyrosineamide N-Isopropylaniline Epinephrine C9H13N2O9P 5'-Uridylic acid C9H13N3O5 Cytidine C9H14ClNO C9H14N2O3 C9H14N3O8P Phenylpropanolamine hydrochloride Metharbital 3'-Cytidylic acid C9H14N4O3 Carnosine C9H15NO3S Captopril C9H15N5O C9H16O4 Minoxidil Nonanedioic acid C9H18O2 C9H19N C9H19N Nonanoic acid N-Butylpiperidine 2,2,6,6-Tetramethylpiperidine Nonylamine 8-Quinolinecarboxylic acid 1-Naphthol 2-Naphthol 1-Naphthylamine 2-Naphthylamine 2-Methylquinoline 4-Methylquinoline 5-Methylquinoline 5-Amino-1-naphthol 6-Methoxyquinoline 1H-Indole-3-acetic acid o-Methylcinnamic acid m-Methylcinnamic acid p-Methylcinnamic acid Tryptamine 5-Hydroxytryptamine 1 2 C9H21N C10H7NO2 C10H8O C10H8O C10H9N C10H9N C10H9N C10H9N C10H9N C10H9NO C10H9NO C10H9NO2 C10H10O2 C10H10O2 C10H10O2 C10H12N2 C10H12N2O t/°C 1 2 1 2 1 2 1 2 3 1 2 3 1 2 1 2 25 25 25 25 25 25 25 25 25 25 25 25 25 20 20 20 25 25 25 23 25 25 25 25 25 25 25 20 20 20 25 20 25 25 25 25 25 25 pKa 9.4 4.17 9.21 6.03 11.49 2.5 2.20 9.31 2.20 9.11 10.1 2.32 8.72 9.96 11.79 7.33 5.77 8.66 9.95 6.4 9.5 4.22 12.5 9.44 8.45 0.8 4.28 6.0 2.73 6.87 9.73 3.7 9.8 4.61 4.53 5.33 4.96 10.47 11.07 10.64 1.82 9.39 9.63 3.92 4.16 5.83 5.67 5.20 3.97 5.03 4.75 4.50 4.44 4.56 10.2 9.8 11.1 DISSOCIATION CONSTANTS OF ORGANIC ACIDS AND BASES (continued) Mol. Form. C10H12N2O5 C10H12N4O3 C10H12O Name C10H13N5O4 Dinoseb Dideoxyinosine 5,6,7,8-Tetrahydro-2naphthalenol Benzenebutanoic acid Propyl 3,4,5-trihydroxybenzoate Adenosine C10H14N2 L-Nicotine C10H14N5O7P 5'-Adenylic acid C10H14O C10H14O C10H14O C10H15N C10H15N C10H15NO C10H15NO C10H17N3O6S 2-tert-Butylphenol 3-tert-Butylphenol 4-tert-Butylphenol N-tert-Butylaniline N,N-Diethylaniline d-Ephedrine l-Ephedrine l-Glutathione C10H18N4O5 L-Argininosuccinic acid C10H12O2 C10H12O5 C10H18O4 Sebacic acid C10H19N C10H19N C10H21N C10H21N Bornylamine Neobornylamine Butylcyclohexylamine 1,2,2,6,6-Pentamethylpiperidine Decylamine 1H-Perimidine 1-Naphthalenecarboxylic acid 2-Naphthalenecarboxylic acid Methyl-1-naphthylamine Iopanoic acid L-Tryptophan C10H23N C11H8N2 C11H8O2 C11H8O2 C11H11N C11H12I3NO2 C11H12N2O2 C11H12N4O3S Sulfamethoxypyridazine C11H13F3N2O3S Mefluidide C11H13NO3 Hydrastinine C11H13N3O3S Sulfisoxazole C11H14N2O Cytisine C11H14O2 C11H14O2 C11H14O2 C11H16N2O2 2-tert-Butylbenzoic acid 3-tert-Butylbenzoic acid 4-tert-Butylbenzoic acid Pilocarpine C11H16N4O4 C11H17N Pentostatin N,N-Diethyl-2-methylaniline Step 1 2 1 2 1 2 1 2 3 4 1 2 3 4 1 2 1 2 t/°C pKa Mol. Form. 25 4.62 9.12 10.48 C11H17NO3 C11H17N3O8 C11H18ClNO3 C11H18N2O3 C11H25N C11H26NO2PS 25 4.76 8.11 25 25 25 25 25 30 3.6 12.4 8.02 3.12 3.8 6.2 10.62 10.12 10.23 7.00 6.57 10.139 9.958 2.12 3.59 8.75 9.65 1.62 2.70 4.26 9.58 4.59 5.59 10.17 10.01 11.23 11.25 25 20 25 10.64 6.35 3.69 25 4.16 27 3.67 4.8 2.46 9.41 6.7 4.6 11.38 5 6.11 13.08 3.54 4.20 4.38 1.6 6.9 5.2 7.24 25 25 25 25 25 10 10 25 25 25 25 25 25 25 25 25 25 1 2 1 2 25 25 25 25 25 25 C12H6Cl4O2S C12H8N2 C12H8N2 C12H10O C12H10O C12H10O C12H11N C12H11N C12H11N C12H11N C12H11N C12H11N3 C12H12N2 C12H12N2O3 C12H13I3N2O3 C12H13N C12H13N C12H14N4O2S C12H14N4O3S C12H17N3O4 C12H20N2O2 C12H21N5O2S2 C12H22O11 C12H22O11 C12H23N C12H27N C13H9N C13H9N C13H10N2 C13H10N2 C13H10O2 C13H10O3 C13H10O3 C13H10O3 C13H11N3 C13H12Cl2O4 C13H12N2O C13H12N2O3S C13H13N C13H14N2O13 C13H15N3O3 TeamLRN Name Step Isoproterenol Tetrodotoxin Methoxamine hydrochloride Amobarbital Undecylamine Methylphosphonothioic acid S[2-[bis(1-isopropyl)amino]ethyl],O-ethylester Bithionol 1 2 1,10-Phenanthroline Phenazine 2-Hydroxybiphenyl 3-Hydroxybiphenyl 4-Hydroxybiphenyl Diphenylamine 2-Aminobiphenyl 3-Aminobiphenyl 4-Aminobiphenyl 2-Benzylpyridine 4-Aminoazobenzene p-Benzidine 1 2 Phenobarbital 1 2 Iocetamic acid N,N-Dimethyl-1naphthylamine N,N-Dimethyl-2naphthylamine Sulfamethazine 1 2 Sulfacytine Agaritine 1 2 Aspergillic acid Nizatidine 1 2 Sucrose α-Maltose Dicyclohexylamine Dodecylamine Acridine Phenanthridine 9-Acridinamine 2-Phenylbenzimidazole 1 2 2-Phenylbenzoic acid 2-Phenoxybenzoic acid 3-Phenoxybenzoic acid 4-Phenoxybenzoic acid 3,6-Acridinediamine Ethacrynic acid Harmine Sulfabenzamide 4-Benzylaniline Harmaline Imazapyr 1 2 t/°C 25 25 25 25 20 25 25 25 25 25 18 18 25 25 20 20 25 25 25 21 25 20 20 20 25 25 25 25 25 25 20 25 25 pKa 8.64 8.76 9.2 8.0 10.63 7.9 4.82 10.50 4.84 1.20 10.01 9.64 9.55 0.79 3.83 4.25 4.35 5.13 2.82 4.65 3.43 7.3 11.8 4 4.83 4.566 7.4 2.65 6.9 3.4 8.86 5.5 2.1 6.8 12.7 12.05 10.4 10.63 5.58 5.58 9.99 5.23 11.91 3.46 3.53 3.95 4.57 9.65 3.50 7.70 4.57 2.17 4.2 1.9 3.6 DISSOCIATION CONSTANTS OF ORGANIC ACIDS AND BASES (continued) Mol. Form. Name Step Ketamine 4-[(Dipropylamino)sulfonyl]benzoic acid C13H21N 2,6-Di-tert-butylpyridine C13H29N (Tridecyl)amine C14H12F3NO4S2 Perfluidone α-Phenylbenzeneacetic acid C14H12O2 C14H12O3 α-Hydroxy-α-phenylbenezeneacetic acid C14H18N4O3 Trimethoprim C14H19NO2 Methylphenidate C14H21N3O3S Tolazamide Atenolol C14H22N2O3 C14H31N Tetradecylamine C15H10ClN3O3 Clonazepam 1 2 C15H11I4NO4 L-Thyroxine 1 2 3 Fenoprofen C15H14O3 C15H15NO2 Mefenamic acid C15H15N3O2 Methyl Red 1 2 C15H17ClN4 NeutralRed C15H19NO2 Tropacocaine C15H19N3O3 Imazethapyr 1 2 C15H21N3O2 Physostigmine 1 2 C15H26N2 Sparteine 1 2 Pentadecylamine C15H33N C16H13ClN2O Valium C16H14ClN3O Chlorodiazepoxide C16H16N2O2 Lysergic acid 1 2 C16H17N3O4S Cephalexin 1 2 C16H19N3O4S Cephradine 1 2 C16H22N2 Lycodine 1 2 C16H35N Hexadecylamine C17H17NO2 Apomorphine 1 2 C17H19NO3 Piperine C17H19NO3 Morphine 1 2 C17H20N4O6 Riboflavin 1 2 C17H20O6 Mycophenolic acid C17H23NO3 Hyoscyamine C17H27NO4 Nadolol Clozapine 1 C18H19ClN4 2 C18H21NO3 Codeine C18H21N3O Dibenzepin C18H32O2 Linoleic acid t/°C C13H16ClNO C13H19NO4S pKa 7.5 5.8 25 25 25 25 25 25 25 25 15 20 20 25 25 18 25 20 25 21 3.58 10.63 2.5 3.94 3.04 6.6 8.9 3.6 9.6 10.62 1.5 10.5 2.2 6.45 10.1 7.3 4.2 2.5 9.5 6.7 4.32 2.1 3.9 6.12 12.24 2.24 9.46 10.61 3.4 4.8 3.44 7.68 5.2 7.3 2.63 7.27 3.97 8.08 10.61 7.0 8.92 12.22 8.21 9.85 1.7 9.69 4.5 9.7 9.67 3.70 7.60 8.21 8.25 7.6 Mol. Form. Name C18H33ClN2O5S Clindamycin C18H39N Octadecylamine C19H10Br4O5S Bromophenol Blue Phenol Red C19H14O5S C19H16ClNO4 Indomethacin C19H17N3O4S2 Cephaloridine Phenylbutazone C19H20N2O2 C19H21N Protriptyline C19H21NO3 Thebaine Cinchonine C19H22N2O C19H22N2O Cinchonidine C19H22N2O2 C19H22O6 C19H23N3O2 C19H23N3O2 C20H14O4 C20H21NO4 C20H23N C20H23N7O7 Cupreine Gibberellic acid Ergometrinine Ergonovine Phenolphthalein Papaverine Amitriptyline Folinic acid C20H24N2O2 Quinine C20H24N2O2 Quinidine C20H26N2O2 C21H14Br4O5S C21H16Br2O5S C21H18O5S C21H21NO6 C21H22N2O2 C21H23ClFNO2 C21H31NO4 C21H35N3O7 Hydroquinine Bromocresol Green Bromocresol Purple CresolRed Hydrastine Strychnine Haloperidol Furethidine Lisinopril C22H18O4 C22H22FN3O2 C22H23NO7 C22H25NO6 C22H25N3O o-Cresolphthalein Droperidol Noscapine Colchicine Benzpiperylon C22H33NO2 C23H26N2O4 Atisine Brucine C24H40O4 C24H40O5 C25H29I2NO3 C25H41NO9 C26H43NO6 C26H45NO7S C27H28Br2O5S C27H38N2O4 C29H32O13 C29H40N2O4 Deoxycholic acid Cholic acid Amiodarone Aconine Glycocholic acid Taurocholic acid Bromothymol Blue Verapamil Etoposide Emetine Step t/°C 25 15 1 2 1 2 25 1 2 3 1 2 1 2 25 25 20 20 25 1 2 3 4 20 1 2 1 2 25 1 2 pKa 7.6 10.60 4.0 7.9 4.5 3.2 4.5 8.2 6.05 5.85 9.92 5.80 10.03 6.57 4.0 7.3 6.8 9.7 6.4 9.4 3.1 4.8 10.4 8.52 4.13 5.4 10.0 5.33 4.7 6.3 8.3 7.8 8.26 8.3 7.48 2.5 4.0 6.7 10.1 9.4 7.64 7.8 12.36 6.73 9.13 12.2 6.04 11.07 6.58 6.4 6.56 9.52 4.4 1.4 7.0 8.6 9.8 5.77 6.64 DISSOCIATION CONSTANTS OF ORGANIC ACIDS AND BASES (continued) Mol. Form. Name C30H23BrO4 C30H48O3 C31H36N2O11 Bromadiolone Oleanolic acid Novobiocin C32H32O13S C33H40N2O9 C34H47NO11 Teniposide Reserpine Aconitine Step 1 2 t/°C pKa Mol. Form. 21 4.04 2.52 4.3 9.1 10.13 6.6 5.88 C36H51NO11 C37H67NO13 C43H58N4O12 Veratridine Erythromycin Rifampin C45H73NO15 C46H56N4O10 C46H58N4O9 Solanine Vincristine Vinblastine TeamLRN Name Step t/°C 1 2 15 1 2 pKa 9.54 8.8 1.7 7.9 6.66 5.4 5.4 7.4 SOLUBILITY PRODUCT CONSTANTS The solubility product constant Ksp is a useful parameter for calculating the aqueous solubility of sparingly soluble compounds under various conditions. It may be determined by direct measurement or calculated from the standard Gibbs energies of formation ∆fG° of the species involved at their standard states. Thus if Ksp = [M+]m [A–]n is the equilibrium constant for the reaction MmAn(s) 1 mM+(aq) + nA– (aq), where MmAn is the slightly soluble substance and M+ and A- are the ions produced in solution by the dissociation of MmAn, then the Gibbs energy change is ∆G° = m ∆fG° (M+,aq) + n ∆fG° (A–,aq) -∆fG° (MmAn, s) The solubility product constant is calculated from the equation ln Ksp = -∆ G°/RT The first table below gives selected values of Ksp at 25°C. Many of these have been calculated from standard state thermodynamic data in References 1 and 2; other values are taken from publications of the IUPAC Solubility Data Project (References 3 to 7). The above formulation is not convenient for treating sulfides because the S-2 ion is usually not present in significant concentrations (see Reference 8). This is due to the hydrolysis reaction S-2 + H2O 1 HS– + OH– which is strongly shifted to the right except in very basic solutions. Furthermore, the equilibrium constant for this reaction, which depends on the second ionization constant of H2S, is poorly known. Therefore it is more useful in the case of sulfides to define a different solubility product Kspa based on the reaction MmSn(s) + 2H+ 1 mM+ + nH2S (aq) Values of Kspa , taken from Reference 8, are given for several sulfides in the auxiliary table following the main table. Additional discussion of sulfide equilibria may be found in References 7 and 9. REFERENCES 1. Wagman, D.D., Evans, W.H., Parker, V.B., Schumm, R.H., Halow, I., Bailey, S.M., Churney, K.L., and Nuttall, R L., The NBS Tables of Chemical Thermodynamic Properties, J. Phys. Chem. Ref. Data, Vol. 11, Suppl. 2, 1982. 2. Garvin, D., Parker, V.B., and White, H.J., CODATA Thermodynamic Tables, Hemisphere, New York, 1987. 3. Solubility Data Series (53 Volumes), International Union of Pure and Applied Chemistry, Pergamon Press, Oxford, 1979—1992. 4. Clever, H.L., and Johnston, F.J., J. Phys. Chem. Ref. Data, 9, 751, 1980. 5. Marcus, Y., J. Phys. Chem. Ref. Data, 9, 1307, 1980. 6. Clever, H.L., Johnson, S.A., and Derrick, M.E., J. Phys. Chem. Ref. Data, 14, 631, 1985. 7. Clever, H.L., Johnson, S.A., and Derrick, M.E., J. Phys. Chem. Ref. Data, 21, 941, 1992. 8. Myers, R.J., J. Chem. Educ., 63, 687, 1986. 9. Licht, S., J. Electrochem. Soc.,135, 2971, 1988. Compound Aluminum phosphate Barium bromate Barium carbonate Barium chromate Barium fluoride Barium hydroxide octahydrate Barium iodate Barium iodate monohydrate Barium molybdate Barium nitrate Barium selenate Barium sulfate Barium sulfite Beryllium hydroxide Bismuth arsenate Formula AlPO4 Ba(BrO3)2 BaCO3 BaCrO4 BaF2 Ba(OH)2⋅8H2O Ba(IO3)2 Ba(IO3)2⋅H2O BaMoO4 Ba(NO3)2 BaSeO4 BaSO4 BaSO3 Be(OH)2 BiAsO4 © 2000 CRC Press LLC TeamLRN Ksp 9.84⋅10-21 2.43⋅10-4 2.58⋅10-9 1.17⋅10-10 1.84⋅10-7 2.55⋅10-4 4.01⋅10-9 1.67⋅10-9 3.54⋅10-8 4.64⋅10-3 3.40⋅10-8 1.08⋅10-10 5.0⋅10-10 6.92⋅10-22 4.43⋅10-10 SOLUBILITY PRODUCT CONSTANTS (continued) Compound Bismuth iodide Cadmium arsenate Cadmium carbonate Cadmium fluoride Cadmium hydroxide Cadmium iodate Cadmium oxalate trihydrate Cadmium phosphate Calcium carbonate (calcite) Calcium fluoride Calcium hydroxide Calcium iodate Calcium iodate hexahydrate Calcium molybdate Calcium oxalate monohydrate Calcium phosphate Calcium sulfate Calcium sulfate dihydrate Calcium sulfite hemihydrate Cesium perchlorate Cesium periodate Cobalt(II) arsenate Cobalt(II) hydroxide (blue) Cobalt(II) iodate dihydrate Cobalt(II) phosphate Copper(I) bromide Copper(I) chloride Copper(I) cyanide Copper(I) iodide Copper(I) thiocyanate Copper(II) arsenate Copper(II) iodate monohydrate Copper(II) oxalate Copper(II) phosphate Europium(III) hydroxide Gallium(III) hydroxide Iron(II) carbonate Iron(II) fluoride Iron(II) hydroxide Iron(III) hydroxide Iron(III) phosphate dihydrate Lanthanum iodate Lead(II) bromide Lead(II) carbonate Lead(II) chloride Lead(II) fluoride Lead(II) hydroxide Lead(II) iodate Lead(II) iodide Lead(II) selenate Lead(II) sulfate Lithium carbonate Lithium fluoride Lithium phosphate Magnesium carbonate Magnesium carbonate trihydrate Magnesium carbonate pentahydrate Magnesium fluoride Magnesium hydroxide Magnesium oxalate dihydrate © 2000 CRC Press LLC Formula BiI3 Cd3(AsO4)2 CdCO3 CdF2 Cd(OH)2 Cd(IO3)2 CdC2O4⋅3H2O Cd3(PO4)2 CaCO3 CaF2 Ca(OH)2 Ca(IO3)2 Ca(IO3)2⋅6H2O CaMoO4 CaC2O4⋅H2O Ca3(PO4)2 CaSO4 CaSO4⋅2H2O CaSO3⋅0.5H2O CsClO4 CsIO4 Co3(AsO4)2 Co(OH)2 Co(IO3)2⋅2H2O Co3(PO4)2 CuBr CuCl CuCN CuI CuSCN Cu3(AsO4)2 Cu(IO3)2⋅H2O CuC2O4 Cu3(PO4)2 Eu(OH)3 Ga(OH)3 FeCO3 FeF2 Fe(OH)2 Fe(OH)3 FePO4⋅2H2O La(IO3)3 PbBr2 PbCO3 PbCl2 PbF2 Pb(OH)2 Pb(IO3)2 PbI2 PbSeO4 PbSO4 Li2CO3 LiF Li3PO4 MgCO3 MgCO3⋅3H2O MgCO3⋅5H2O MgF2 Mg(OH)2 MgC2O4⋅2H2O Ksp 7.71⋅10-19 2.2⋅10-33 1.0⋅10-12 6.44⋅10-3 7.2⋅10-15 2.5⋅10-8 1.42⋅10-8 2.53⋅10-33 3.36⋅10-9 3.45⋅10-11 5.02⋅10-6 6.47⋅10-6 7.10⋅10-7 1.46⋅10-8 2.32⋅10-9 2.07⋅10-33 4.93⋅10-5 3.14⋅10-5 3.1⋅10-7 3.95⋅10-3 5.16⋅10-6 6.80⋅10-29 5.92⋅10-15 1.21⋅10-2 2.05⋅10-35 6.27⋅10-9 1.72⋅10-7 3.47⋅10-20 1.27⋅10-12 1.77⋅10-13 7.95⋅10-36 6.94⋅10-8 4.43⋅10-10 1.40⋅10-37 9.38⋅10-27 7.28⋅10-36 3.13⋅10-11 2.36⋅10-6 4.87⋅10-17 2.79⋅10-39 9.91⋅10-16 7.50⋅10-12 6.60⋅10-6 7.40⋅10-14 1.70⋅10-5 3.3⋅10-8 1.43⋅10-20 3.69⋅10-13 9.8⋅10-9 1.37⋅10-7 2.53⋅10-8 8.15⋅10-4 1.84⋅10-3 2.37⋅10-11 6.82⋅10-6 2.38⋅10-6 3.79⋅10-6 5.16⋅10-11 5.61⋅10-12 4.83⋅10-6 SOLUBILITY PRODUCT CONSTANTS (continued) Compound Magnesium phosphate Manganese(II) carbonate Manganese(II) iodate Manganese(II) oxalate dihydrate Mercury(I) bromide Mercury(I) carbonate Mercury(I) chloride Mercury(I) fluoride Mercury(I) iodide Mercury(I) oxalate Mercury(I) sulfate Mercury(I) thiocyanate Mercury(II) bromide Mercury(II) iodide Neodymium carbonate Nickel(II) carbonate Nickel(II) hydroxide Nickel(II) iodate Nickel(II) phosphate Palladium(II) thiocyanate Potassium hexachloroplatinate Potassium perchlorate Potassium periodate Praseodymium hydroxide Radium iodate Radium sulfate Rubidium perchlorate Scandium fluoride Scandium hydroxide Silver(I) acetate Silver(I) arsenate Silver(I) bromate Silver(I) bromide Silver(I) carbonate Silver(I) chloride Silver(I) chromate Silver(I) cyanide Silver(I) iodate Silver(I) iodide Silver(I) oxalate Silver(I) phosphate Silver(I) sulfate Silver(I) sulfite Silver(I) thiocyanate Strontium arsenate Strontium carbonate Strontium fluoride Strontium iodate Strontium iodate monohydrate Strontium iodate hexahydrate Strontium sulfate Thallium(I) bromate Thallium(I) bromide Thallium(I) chloride Thallium(I) chromate Thallium(I) iodate Thallium(I) iodide Thallium(I) thiocyanate Thallium(III) hydroxide Tin(II) hydroxide Formula Ksp Mg3(PO4)2 MnCO3 Mn(IO3)2 MnC2O4⋅2H2O Hg2Br2 Hg2CO3 Hg2Cl2 Hg2F2 Hg2I2 Hg2C2O4 Hg2SO4 Hg2(SCN)2 HgBr2 HgI2 Nd2(CO3)3 NiCO3 Ni(OH)2 Ni(IO3)2 Ni3(PO4)2 Pd(SCN)2 K2PtCl6 KClO4 KIO4 Pr(OH)3 Ra(IO3)2 RaSO4 RbClO4 ScF3 Sc(OH)3 AgCH3COO Ag3AsO4 AgBrO3 AgBr Ag2CO3 AgCl Ag2CrO4 AgCN AgIO3 AgI Ag2C2O4 Ag3PO4 Ag2SO4 Ag2SO3 AgSCN Sr3(AsO4)2 SrCO3 SrF2 Sr(IO3)2 Sr(IO3)2⋅H2O Sr(IO3)2⋅6H2O SrSO4 TlBrO3 TlBr TlCl Tl2CrO4 TlIO3 TlI TlSCN Tl(OH)3 Sn(OH)2 1.04⋅10-24 2.24⋅10-11 4.37⋅10-7 1.70⋅10-7 6.40⋅10-23 3.6⋅10-17 1.43⋅10-18 3.10⋅10-6 5.2⋅10-29 1.75⋅10-13 6.5⋅10-7 3.2⋅10-20 6.2⋅10-20 2.9⋅10-29 1.08⋅10-33 1.42⋅10-7 5.48⋅10-16 4.71⋅10-5 4.74⋅10-32 4.39⋅10-23 7.48⋅10-6 1.05⋅10-2 3.71⋅10-4 3.39⋅10-24 1.16⋅10-9 3.66⋅10-11 3.00⋅10-3 5.81⋅10-24 2.22⋅10-31 1.94⋅10-3 1.03⋅10-22 5.38⋅10-5 5.35⋅10-13 8.46⋅10-12 1.77⋅10-10 1.12⋅10-12 5.97⋅10-17 3.17⋅10-8 8.52⋅10-17 5.40⋅10-12 8.89⋅10-17 1.20⋅10-5 1.50⋅10-14 1.03⋅10-12 4.29⋅10-19 5.60⋅10-10 4.33⋅10-9 1.14⋅10-7 3.77⋅10-7 4.55⋅10-7 3.44⋅10-7 1.10⋅10-4 3.71⋅10-6 1.86⋅10-4 8.67⋅10-13 3.12⋅10-6 5.54⋅10-8 1.57⋅10-4 1.68⋅10-44 5.45⋅10-27 © 2000 CRC Press LLC TeamLRN SOLUBILITY PRODUCT CONSTANTS (continued) Compound Formula Ksp Yttrium carbonate Yttrium fluoride Yttrium hydroxide Yttrium iodate Zinc arsenate Zinc carbonate Zinc carbonate monohydrate Zinc fluoride Zinc hydroxide Zinc iodate dihydrate Zinc oxalate dihydrate Zinc selenide Zinc selenite monohydrate Y2(CO3)3 YF3 Y(OH)3 Y(IO3)3 Zn3(AsO4)2 ZnCO3 ZnCO3⋅H2O ZnF2 Zn(OH)2 Zn(IO3)2⋅2H2O ZnC2O4⋅2H2O ZnSe ZnSeO3⋅H2O 1.03⋅10-31 8.62⋅10-21 1.00⋅10-22 1.12⋅10-10 2.8⋅10-28 1.46⋅10-10 5.42⋅10-11 3.04⋅10-2 3⋅10-17 4.1⋅10-6 1.38⋅10-9 3.6⋅10-26 1.59⋅10-7 Sulfides Compound Cadmium sulfide Copper(II) sulfide Iron(II) sulfide Lead(II) sulfide Manganese(II) sulfide (green) Mercury(II) sulfide (red) Mercury(II) sulfide (black) Silver(I) sulfide Tin(II) sulfide Zinc sulfide (sphalerite) Zinc sulfide (wurtzite) © 2000 CRC Press LLC Formula CdS CuS FeS PbS MnS HgS HgS Ag2S SnS ZnS ZnS Kspa 8⋅10-7 6⋅10-16 6⋅102 3⋅10-7 3⋅107 4⋅10-33 2⋅10-32 6⋅10-30 1⋅10-5 2⋅10-4 3⋅10-2
© Copyright 2026 Paperzz