Dissociation Constants of Organic Acids and Bases [PDF]

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

⇌ 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

HA ⇌ H+ + A-

i.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+ ⇌ H+ + B



In older literature, an ionization constant Kb was used for the reaction B + H2O Mol. form. CHNO CH2N2 CH2O CH2O2 CH3NO2 CH3NS2 CH4N2O CH4N2S CH4O CH4S CH5N CH5NO CH5N3 C2HCl3O C2HCl3O2 C2HF3O2 C2H2Cl2O2 C2H2O3 C2H2O4

Name 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 C2H4N2 C2H4O C2H4OS C2H4O2 C2H4O2S C2H4O3 C2H5N

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 Aminoacetonitrile Acetaldehyde Thioacetic acid Acetic acid Thioglycolic acid Glycolic acid Ethyleneimine

8-42

Step

1 2

t/°C 25 29 25 25 25 25 25 25 25 25 25 25 25 20 25 25 25 25 25 25 25 25 25 25 25 24 20 20 25 25 25 25 25 25 25

pKa 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 5.34 13.57 3.33 4.756 3.68 3.83 8.04

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. O’Neil, M.J., Ed., The Merck Index, 14th Edition, Merck & Co., Whitehouse Station, NJ, 2006. Mol. form. C2H5NO C2H5NO2 C2H5NO2 C2H5NO2

Name Acetamide Acetohydroxamic acid Nitroethane Glycine

C2H6N2 C2H6O C2H6OS C2H6O2 C2H7AsO2

Ethanimidamide Ethanol 2-Mercaptoethanol Ethyleneglycol Dimethylarsinic acid

C2H7N C2H7N C2H7NO C2H7NO3S

Ethylamine Dimethylamine Ethanolamine

C2H7NS

2-Aminoethanesulfonic   acid Cysteamine

C2H7N5

Biguanide

C2H8N2

1,2-Ethanediamine

C2H8O7P2

1-Hydroxy-1,1  diphosphonoethane

C3H2O2 C3H3NO C3H3NO C3H3NO2 C3H3NS C3H3N3O3

2-Propynoic acid Oxazole Isoxazole Cyanoacetic acid Thiazole Cyanuric acid

C3H4N2 C3H4N2

1H-Pyrazole Imidazole

Step

1 2

1 2

1 2 1 2 1 2 1 2 1 2 3 4

1 2 3

t/°C 25 25 25 25 25 25 25 25 25 25 25 25 25 25 25 25 25

25 25

25 33 25 25 25

25 25

pKa 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 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

Dissociation Constants of Organic Acids and Bases Mol. form. C3H4N2S C3H4O C3H4O2 C3H4O3 C3H4O4

Name 2-Thiazolamine Propargyl alcohol Acrylic acid Pyruvic acid Malonic acid

C3H4O5

Hydroxypropanedioic   acid 3-Bromopropanoic acid 2-Chloropropanoic acid 3-Chloropropanoic acid 3-Aminopropanenitrile

C3H5BrO2 C3H5ClO2 C3H5ClO2 C3H6N2 C3H6N6 C3H6O C3H6O2 C3H6O2S C3H6O3 C3H6O3 C3H6O4 C3H7N C3H7N C3H7NO C3H7NO2

1,3,5-Triazine-2,4,6  triamine 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

C3H7NO3

L-Serine

C3H7NO5S

DL-Cysteic acid

C3H7N3O2 C3H8O2

Glycocyamine

C3H8O3 C3H9N C3H9N C3H9N C3H9NO C3H9NO C3H10N2

Ethylene glycol   monomethyl ether Glycerol Propylamine Isopropylamine Trimethylamine 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

Flucytosine Pyrazine Pyrimidine Pyridazine Uracil Barbituric acid Alloxanic acid

Step

1 2 1 2

1 2 1 2 1 2 1 2 3 1 2 1 2 3

1 2 1 2 1 2 1 2

t/°C 20 25 25 25 25 25

25 25 25 20 25

pKa 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 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

25 25 25 25 25 20 25 25 25 25 20 20 20 20

14.15 10.54 10.63 9.80 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

20 20 20 25 25 25

8-43 Mol. form. C4H4N4O2 C4H4O2 C4H4O4

Name 5-Nitropyrimidinamine 2-Butynoic acid Maleic acid

C4H4O4

Fumaric acid

C4H4O5

Oxaloacetic acid

C4H5N C4H5NO2 C4H5N3 C4H5N3 C4H5N3O

Pyrrole Succinimide 2-Pyrimidinamine 4-Pyrimidinamine Cytosine

C4H5N3O2 C4H6N2 C4H6N4O3 C4H6N4O3S2 C4H6O2 C4H6O2 C4H6O2 C4H6O3 C4H6O3 C4H6O4

6-Methyl-1,2,4-triazine  3,5(2H,4H)-dione 1-Methylimidazol Allantoin Acetazolamide trans-Crotonic acid 3-Butenoic acid Cyclopropanecarboxylic acid 2-Oxobutanoic acid Acetoacetic acid Succinic acid

C4H6O4

Methylmalonic acid

C4H6O5

Malic acid

C4H6O6

DL-Tartaric acid

C4H6O6

meso-Tartaric acid

C4H6O6

L-Tartaric acid

C4H6O8 C4H7ClO2 C4H7ClO2 C4H7ClO2 C4H7NO2 C4H7NO3 C4H7NO4

Dihydroxytartaric acid 2-Chlorobutanoic acid 3-Chlorobutanoic acid 4-Chlorobutanoic acid 4-Cyanobutanoic acid N-Acetylglycine Iminodiacetic acid

C4H7NO4

L-Aspartic acid

C4H7N3O

Creatinine

C4H7N5 C4H8N2O3

2,4,6-Pyrimidinetriamine L-Asparagine

C4H8N2O3

N-Glycylglycine

C4H8O2 C4H8O2 C4H8O3 C4H8O3 C4H8O3 C4H9N

Butanoic acid 2-Methylpropanoic acid 3-Hydroxybutanoic acid, (±) 4-Hydroxybutanoic acid Ethoxyacetic acid Pyrrolidine

Step

1 2 1 2 1 2 3

1 2

1 2 1 2 1 2 1 2 1 2 1 2

1 2 1 2 3 1 2 1 2 1 2

t/°C 20 25 25 25 25 25 25 25 25 25 25 20 20

pKa 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

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 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

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 20 25 25 20 25 25 18 25

Dissociation Constants of Organic Acids and Bases

8-44 Mol. form. C4H9NO C4H9NO2

Name Morpholine 2-Methylalanine

C4H9NO2 C4H9NO2

N,N-Dimethylglycine DL-2-Aminobutanoic acid

C4H9NO2

4-Aminobutanoic acid

C4H9NO2S

DL-Homocysteine

C4H9NO3

L-Threonine

C4H9NO3

L-Homoserine

C4H9N3O2

Creatine

C4H10N2

Piperazine

C4H10N2O2

2,4-Diaminobutanoic acid

C4H10O4 C4H11N C4H11N C4H11N C4H11N C4H11NO3

1,2,3,4-Butanetetrol Butylamine sec-Butylamine tert-Butylamine Diethylamine

C4H12N2

Tris(hydroxymethyl)   methylamine 1,4-Butanediamine

C5H4BrN C5H4ClN C5H4ClN C5H4ClN C5H4FN C5H4N2O2 C5H4N4

3-Bromopyridine 2-Chloropyridine 3-Chloropyridine 4-Chloropyridine 2-Fluoropyridine 4-Nitropyridine 1H-Purine

C5H4N4O C5H4N4O C5H4N4O3 C5H4N4S

Hypoxanthine Allopurinol Uric acid

C5H4O2S C5H4O2S C5H4O3 C5H4O3 C5H5N C5H5NO

1,7-Dihydro-6H  purine-6-thione 2-Thiophenecarboxylic acid 3-Thiophenecarboxylic acid 2-Furancarboxylic acid 3-Furancarboxylic acid Pyridine 2-Pyridinol

C5H5NO

3-Pyridinol

C5H5NO

4-Pyridinol

C5H5NO

2(1H)-Pyridinone

C5H5NO C5H5NO2

Pyridine-1-oxide 1H-Pyrrole-2-carboxylic   acid

Step 1 2 1 2 1 2 1 2 3 1 2 1 2 1 2 1 2 1 2 3

t/°C 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

1 2

1 2

1 2

1 2 1 2 1 2 1 2

25 25 25 25 25 25 25 25 20 20 25 12

25 25 25 25 25 20 20 20 20 20 20 20 20 24 20

pKa 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 10.80 9.63 2.84 0.49 2.81 3.83 -0.44 1.61 2.30 8.96 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

Mol. form. C5H5NO2 C5H5N3O C5H5N5

Name

1H-Pyrrole-3-carboxylic   acid Pyrazinecarboxamide Adenine

C5H5N5O C5H6N2 C5H6N2 C5H6N2 C5H6N2 C5H6N2O2 C5H6O4

Guanine 2-Pyridinamine 3-Pyridinamine 4-Pyridinamine 2-Methylpyrazine Thymine

C5H6O4

trans-1-Propene-1,2  dicarboxylic acid

C5H6O4 C5H6O5 C5H7NO3

1,1-Cyclopropanedi  carboxylic acid

1-Propene-2,3  dicarboxylic acid 2-Oxoglutaric acid

C5H7NO3 C5H7N3 C5H7N3 C5H7N3O4 C5H8N2 C5H8N4O3S2 C5H8O2 C5H8O4 C5H8O4

5,5-Dimethyl-2,4  oxazolidinedione L-Pyroglutamic acid 2,5-Pyridinediamine Methylaminopyrazine Azaserine 2,4-Dimethylimidazole Methazolamide trans-3-Pentenoic acid Dimethylmalonic acid Glutaric acid

C5H8O4

Methylsuccinic acid

C5H9NO2

L-Proline

C5H9NO3 C5H9NO3

5-Amino-4-oxopentanoic   acid trans-4-Hydroxyproline

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

Step

1 2

1 2 1 2 1 2 1 2

t/°C 20

pKa 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

25 20 25 25

1 2 1 2 1 2 1 2 1 2 1 2 3 1 2 1 2 1 2

1 2

25 25 18 25 25 25 25 25 25 25 25 25 25 25 25 25 25 25 25 25 25 20 25 25 20 25 25 18 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 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

Dissociation Constants of Organic Acids and Bases Mol. form. C5H11NO2

Name DL-Norvaline

C5H11NO2

L-Norvaline

C5H11NO2

N-Propylglycine

C5H11NO2

5-Aminopentanoic acid

C5H11NO2 C5H11NO2S

Betaine L-Methionine

C5H12N2O C5H12N2O2

Tetramethylurea L-Ornithine

C5H13N C5H13N C5H13N C5H13N C5H13N C5H13N C5H14NO C5H14N2

Pentylamine 3-Pentanamine 3-Methyl-1-butanamine 2-Methyl-2-butanamine 2,2-Dimethylpropylamine Diethylmethylamine Choline 1,5-Pentanediamine

C6H3Cl3N2O2 C6H3N3O7 C6H4Cl2O C6H4N2O5 C6H4N2O5 C6H4N4 C6H5BrO C6H5BrO C6H5BrO C6H5Br2N C6H5ClO C6H5ClO C6H5ClO C6H5Cl2N C6H5FO C6H5FO C6H5FO C6H5IO C6H5IO C6H5IO C6H5NO C6H5NO C6H5NO2 C6H5NO2

4-Amino-3,5,6-trichloro  2-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 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

C6H5NO2

3-Pyridinecarboxylic acid

C6H5NO2

4-Pyridinecarboxylic acid

C6H5NO3 C6H5NO3 C6H5NO3 C6H5N3 C6H5N5O

2-Nitrophenol 3-Nitrophenol 4-Nitrophenol 1H-Benzotriazole

C6H5N5O2

2-Amino-4  hydroxypteridine Xanthopterin

Step 1 2 1 2 1 2 1 2 1 2 1 2 3

1 2

1 2 1 2 1 2

1 2 2

t/°C

25 25 25 25 25 25 0 25 25 25 25 25 25 17 25 19 25 25 25 25 25

24 25 25 15 20 25 25 25 25 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

pKa 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 0.42 7.44 4.07 5.15 4.05 8.45 9.03 9.37 2.34 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

8-45 Mol. form. C6H6BrN C6H6BrN C6H6BrN C6H6ClN C6H6ClN C6H6ClN C6H6FN C6H6FN C6H6FN C6H6IN C6H6IN C6H6IN C6H6N2O C6H6N2O

Name 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

C6H6N2O2 C6H6N2O2 C6H6N2O2 C6H6O C6H6O2

2-Pyridinecarbox  aldehyde oxime 2-Nitroaniline 3-Nitroaniline 4-Nitroaniline Phenol p-Hydroquinone

C6H6O2

Pyrocatechol

C6H6O2

Resorcinol

C6H6O2S C6H6O3S C6H6O4

Benzenesulfinic acid Benzenesulfonic acid

C6H6O4S C6H6O4S C6H6O6 C6H6O6

1 2 1 2 1 2

3-Hydroxybenzene  sulfonic acid 4-Hydroxybenzene  sulfonic acid cis-1-Propene-1,2,3  tricarboxylic acid

C6H6S C6H7BO2 C6H7N C6H7N C6H7N C6H7N C6H7NO C6H7NO

3-Aminophenol

C6H7NO

4-Aminophenol

C6H7NO C6H7NO C6H7NO C6H7NO3S

2-Methoxypyridine 3-Methoxypyridine 4-Methoxypyridine

C6H7NO3S

3-Aminobenzenesulfonic   acid

C6H8N2 C6H8N2

1 2

5-Hydroxy-2-(hydroxy  methyl)-4H-pyran-4-one

trans-1-Propene-1,2,3  tricarboxylic acid Benzenethiol Benzeneboronic acid Aniline 2-Methylpyridine 3-Methylpyridine 4-Methylpyridine 2-Aminophenol

C6H7NO3S

Step 3

1 2

1 2 1 2 1 2

2-Aminobenzenesulfonic   acid

4-Aminobenzenesulfonic   acid N-Methylpyridinamine o-Phenylenediamine

1

t/°C 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

pKa 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

25

9.11

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

25

3.74

25

3.23

20 20

9.65 4.57

Dissociation Constants of Organic Acids and Bases

8-46 Mol. form.

Name

C6H8N2

m-Phenylenediamine

C6H8N2

p-Phenylenediamine

C6H8N2 C6H8O2 C6H8O2 C6H8O4

Phenylhydrazine 2,4-Hexadienoic acid 1,3-Cyclohexanedione

C6H8O6

2,2-Dimethyl-1,3  dioxane-4,6-dione L-Ascorbic acid

C6H8O7

Citric acid

C6H8O7

Isocitric acid

C6H9NO6

Nitrilotriacetic acid

C6H9NO6

L-γ-Carboxyglutamic acid

C6H9N3

4,6-Dimethylpyrimi  dinamine L-Histidine

C6H9N3O2 C6H10O2 C6H10O3 C6H10O4 C6H10O4 C6H11NO2

Cyclopentanecarboxylic   acid Ethyl acetoacetate 3-Methylglutaric acid Adipic acid

C6H11NO3 C6H11NO4

2-Piperidinecarboxylic   acid Adipamic acid 2-Aminoadipic acid

C6H11N3O4

N-(N-Glycylglycyl)glycine

C6H11N3O4

Glycylasparagine

C6H12N2

Triethylenediamine

C6H12N2O4S2

L-Cystine

C6H12O2 C6H12O2 C6H12O6 C6H12O6 C6H12O6 C6H13N C6H13N C6H13N C6H13NO

Hexanoic acid 4-Methylpentanoic acid β-D-Fructose α-D-Glucose D-Mannose Cyclohexylamine 1-Methylpiperidine 1,2-Dimethylpyrrolidine N-Ethylmorpholine

Step 2 1 2 1 2

t/°C 20 20 20 20 20 15 25 25

pKa 0.80 5.11 2.50 6.31 2.97 8.79 4.76 5.26 5.1

1 2 1 2 3 1 2 3 1 2 3 1 2 3 4

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

1 2 3

25 25 25 25

1.80 6.04 9.33 4.99

25 25 18 18 25 25 25 25 25 25 25 25 25 18

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

1 2 1 2 1 2 3 1 2 1 2 1 2 1 2 3 4

25 18 25 25 25 25 25 26 25

Mol. form. C6H13NO2

L-Leucine

C6H13NO2

L-Isoleucine

C6H13NO2

L-Norleucine

C6H13NO2

6-Aminohexanoic acid

C6H13NO4

N,N-Bis(2-hydroxy  ethyl)glycine Citrulline

C6H13N3O3 C6H14N2 C6H14N2 C6H14N2

Name

cis-1,2-Cyclohexane  diamine trans-1,2-Cyclohexane  diamine

C6H14N2O2

cis-2,5-Dimethyl  piperazine L-Lysine

C6H14N4O2

L-Arginine

C6H14O6 C6H15N C6H15N C6H15N C6H15NO3 C6H16N2

D-Mannitol Hexylamine Diisopropylamine Triethylamine Triethanolamine 1,6-Hexanediamine

C6H16N2

N,N,N’,N’-Tetramethyl  1,2-ethanediamine Hexamethyldisilazane Pentafluorobenzoic acid

C6H19NSi2 C7HF5O2 C7H3Br2NO C7H3N3O8 C7H4Cl3NO3 C7H4N2O6 C7H5BrO2 C7H5BrO2 C7H5BrO2 C7H5ClO2 C7H5ClO2 C7H5ClO2 C7H5FO2 C7H5FO2 C7H5FO2 C7H5F3O C7H5F3O C7H5IO2 C7H5IO2 C7H5IO2 C7H5NO C7H5NO C7H5NO C7H5NO3S C7H5NO4 C7H5NO4 C7H5NO4

3,5-Dibromo-4  hydroxybenzonitrile 2,4,6-Trinitrobenzoic acid Triclopyr 2,4-Dinitrobenzoic acid 2-Bromobenzoic acid 3-Bromobenzoic acid 4-Bromobenzoic acid 2-Chlorobenzoic acid 3-Chlorobenzoic acid 4-Chlorobenzoic acid 2-Fluorobenzoic acid 3-Fluorobenzoic acid 4-Fluorobenzoic acid 2-(Trifluoromethyl)phenol 3-(Trifluoromethyl)phenol 2-Iodobenzoic acid 3-Iodobenzoic acid 4-Iodobenzoic acid 2-Hydroxybenzonitrile 3-Hydroxybenzonitrile 4-Hydroxybenzonitrile Saccharin 2-Nitrobenzoic acid 3-Nitrobenzoic acid 4-Nitrobenzoic acid

Step 1 2 1 2 1 2 1 2 2

t/°C 25 25 25 25 25 25 25 25 20

pKa 2.33 9.74 2.32 9.76 2.34 9.83 4.37 10.80 8.35

1 2 1 2 1 2 1 2 1 2 3 1 2 3

25 25 20 20 20 20 25 25 25 25 25 25 25 25 18 25 25 25 25 0 0 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 7.76 11.86 10.76 10.40 8.26 7.55 1.75 4.06

1 2 1 2

25

25 25 25 25 25 25 25 25 25 25 25 25 25 25 25 25 25 25 25 18 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

Dissociation Constants of Organic Acids and Bases Mol. form. C7H5NO4 C7H5NO4 C7H5NO4 C7H5NO4

Name

2,3-Pyridinedicarboxylic   acid 2,4-Pyridinedicarboxylic   acid 2,6-Pyridinedicarboxylic   acid 3,5-Pyridinedicarboxylic   acid Chlorothiazide

C7H6ClN3O4S2 C7H6F3N C7H6F3N C7H6N2 C7H6N2 C7H6N2 C7H6N2 C7H6O C7H6O2 C7H6O2 C7H6O2 C7H6O2 C7H6O3

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

C7H6O3

3-Hydroxybenzoic acid

C7H6O3

4-Hydroxybenzoic acid

C7H6O4

2,4-Dihydroxybenzoic acid

C7H6O4 C7H6O4

2,5-Dihydroxybenzoic acid 3,4-Dihydroxybenzoic acid

C7H6O4 C7H6O5

3,5-Dihydroxybenzoic acid

C7H6O5 C7H7NO C7H7NO2

3,4,5-Trihydroxybenzoic   acid Benzamide Aniline-2-carboxylic acid

C7H7NO2

Aniline-3-carboxylic acid

C7H7NO2

Aniline-4-carboxylic acid

C7H7NO3 C7H8ClN3O4S2

4-Amino-2-hydroxy  benzoic acid Hydrochlorothiazide

C7H8N4O2 C7H8N4O2 C7H8O C7H8O C7H8O C7H8OS C7H8O2 C7H8O2 C7H8O2 C7H8S C7H9N

Theobromine Theophylline o-Cresol m-Cresol p-Cresol 4-(Methylthio)phenol 2-Methoxyphenol 3-Methoxyphenol 4-Methoxyphenol Benzenemethanethiol Benzylamine

Step 1 2 1

t/°C 25 25 25

pKa 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 25 25 25 25 25 25 25 25 25 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 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

1 2

1 2 1 2 1 2 1 2 3 1 1 2 3 1

2,4,6-Trihydroxybenzoic   acid

1 2 1 2 1 2

1 2 1

18 25 25 25 25 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

8-47 Mol. form. C7H9N C7H9N C7H9N C7H9N C7H9N C7H9N C7H9N C7H9N C7H9N C7H9N C7H9N C7H9NO C7H9NO C7H9NO C7H9NS C7H9NS C7H9N5

Name 2-Methylaniline 3-Methylaniline 4-Methylaniline N-Methylaniline 2-Ethylpyridine 2,3-Dimethylpyridine 2,4-Dimethylpyridine 2,5-Dimethylpyridine 2,6-Dimethylpyridine 3,4-Dimethylpyridine 3,5-Dimethylpyridine 2-Methoxyaniline 3-Methoxyaniline 4-Methoxyaniline 2-(Methylthio)aniline 4-(Methylthio)aniline 2-Dimethylaminopurine

C7H11N3O2

L-1-Methylhistidine

C7H11N3O2

L-3-Methylhistidine

C7H12O2 C7H12O4

Cyclohexanecarboxylic acid Heptanedioic acid

C7H12O4 C7H13NO4

Butylpropanedioic acid α-Ethylglutamic acid

C7H14O2 C7H14O6 C7H15N C7H15N C7H15NO3 C7H17N C7H17N C8H5NO2 C8H5NO2 C8H6N2 C8H6N2 C8H6N2 C8H6N2 C8H6N4O5 C8H6O3 C8H6O3 C8H6O4

Heptanoic acid α-Methylglucoside 1-Ethylpiperidine 1,2-Dimethylpiperidine,(±) Carnitine Heptylamine 2-Heptanamine 3-Cyanobenzoic acid 4-Cyanobenzoic acid Cinnoline Quinazoline Quinoxaline Phthalazine Nitrofurantoin 3-Formylbenzoic acid 4-Formylbenzoic acid Phthalic acid

C8H6O4

Isophthalic acid

C8H6O4

Terephthalic acid

C8H7ClO2 C8H7ClO2 C8H7ClO2 C8H7ClO3 C8H7ClO3 C8H7NO4 C8H7NO4 C8H7NO4 C8H8F3N3O4S2

2-Chlorobenzeneacetic acid 3-Chlorobenzeneacetic acid 4-Chlorobenzeneacetic acid 2-Chlorophenoxyacetic acid 3-Chlorophenoxyacetic acid 2-Nitrobenzeneacetic acid 3-Nitrobenzeneacetic acid 4-Nitrobenzeneacetic acid Hydroflumethiazide

Step

1 2 1 2 3 1 2 3 1 2 1 1 2

1 2 1 2 1 2

1

t/°C 25 25 25 25 25 25 25 25 25 25 25 25 25 25 25 25 20 20 25 25 25 25 25 25 25 25 25 5 25 25 25 25 23 25 25 25 19 25 25 20 29 20 20 25 25 25 25 25 25 25 25 25 25 25 25 25 25 25 25

pKa 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 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

Dissociation Constants of Organic Acids and Bases

8-48 Mol. form. C8H8N2 C8H8O2 C8H8O2 C8H8O2 C8H8O2 C8H8O2 C8H8O2 C8H8O2 C8H8O3 C8H8O3 C8H8O3 C8H8O3 C8H8O3 C8H8O4 C8H9NO C8H9NO2 C8H9NO2 C8H9NO2 C8H9NO2 C8H10BrN C8H10ClN C8H10ClN C8H10N2O2

Name 2-Methyl-1H-benzimidazole o-Toluic acid m-Toluic acid p-Toluic acid Benzeneacetic acid 1-(2-Hydroxyphenyl)ethanone 1-(3-Hydroxyphenyl)ethanone 1-(4-Hydroxyphenyl)ethanone 2-Methoxybenzoic acid 3-Methoxybenzoic acid 4-Methoxybenzoic acid Phenoxyacetic acid Mandelic acid

25 25 25 25 25 25 25 25 25 25 25 25 25 25

pKa 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

C9H6BrN C9H7ClO2

3-Bromoquinoline

25

5.10

C9H7ClO2

25

5.04

C9H7ClO2

trans-m-Chlorocinnamic   acid

25 25

1.83 4.39 4.23

C9H7N C9H7N C9H7NO

trans-p-Chlorocinnamic   acid Quinoline Isoquinoline 2-Quinolinol

20

3.83

C9H7NO

3-Quinolinol

20

4.39

C9H7NO

4-Quinolinol

25

2.62

C9H7NO

6-Quinolinol 8-Quinolinol

C9H7NO

7-Isoquinolinol

1 2 1 2

25 25 25 25

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

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

C9H7NO

1 2

25 25 25 25 25 28 25 28 25 25

25 15 15 25 25

6.84 5.4 4.52 3.80 3.80 3.18 3.25

2,5-Hydroxybenzeneacetic acid Acetanilide 2-(Methylamino)benzoic   acid 3-(Methylamino)benzoic   acid 4-(Methylamino)benzoic   acid N-Phenylglycine 4-Bromo-N,N  dimethylaniline

1 2

3-Chloro-N,N  dimethylaniline 4-Chloro-N,N  dimethylaniline

C8H11N C8H11N C8H11N C8H11N C8H11N C8H11NO C8H11NO C8H11NO C8H11NO

N,N-Dimethyl-3  nitroaniline N-Ethylaniline N,N-Dimethylaniline 2,6-Dimethylaniline Benzeneethanamine 2,4,6-Trimethylpyridine 2-Ethoxyaniline 3-Ethoxyaniline 4-Ethoxyaniline 4-(2-Aminoethyl)phenol

C8H11NO C8H11NO2

2-(2-Methoxyethyl)pyridine Dopamine

C8H11NO3

Norepinephrine

C8H11N3O6 C8H11N5

6-Azauridine Phenylbiguanide

C8H12N2O3 C8H12O2

Barbital

C8H13NO2 C8H14O2S2 C8H14O4 C8H15NO C8H15NO C8H16N2O3 C8H16N2O3

Step 2 1

5,5-Dimethyl-1,3  cyclohexanedione Arecoline Thioctic acid Octanedioic acid Tropine Pseudotropine N-Glycylleucine N-Leucylglycine

1 2

1

1

t/°C

Mol. form.

Name

C8H16N2O4S2

Homocystine

C8H16O2 C8H16O2 C8H17N C8H17N C8H17NO

Octanoic acid 2-Propylpentanoic acid 2-Propylpiperidine,(S) 2,2,4-Trimethylpiperidine

C8H19N C8H19N C8H19N C8H20N2

C9H8O4 C9H9Br2NO3 C9H9ClO2 C9H9ClO2 C9H9ClO2 C9H9I2NO3

trans-6-Propyl-3  piperidinol,(3S) Octylamine N-Methyl-2-heptanamine Dibutylamine 1,8-Octanediamine

Step 2 1 2 3 4

30

1 2

trans-o-Chlorocinnamic   acid

α-Methylenebenezene  acetic acid 2-(Acetyloxy)benzoic acid 3,5-Dibromo-L-tyrosine

1 2 1 2 1 2 1 2 1 2 1 2

1 2 3

3-(3-Chlorophenyl)  propanoic acid

1

pKa 8.2 1.59 2.54 8.52 9.44 4.89 4.6 10.9 11.04 10.3

25 17 21 20 20 25 25

10.65 10.99 11.25 11.00 10.1 2.69 4.23

25

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

3-(2-Chlorophenyl)  propanoic acid

3-(4-Chlorophenyl)  propanoic acid L-3,5-Diiodotyrosine

t/°C 25 25 25 25 25 25

25

25

3.48 2.17 6.45 7.60 4.58

25

4.59

25

4.61

25

2.12

Dissociation Constants of Organic Acids and Bases Mol. form.

Name

C9H9NO3 C9H9NO4

N-Benzoylglycine

C9H9NO4

3-(4-Nitrophenyl)  propanoic acid Carbendazim Sulfathiazole L-3-Iodotyrosine

C9H9N3O2 C9H9N3O2S2 C9H10INO3 C9H10N2 C9H10O2 C9H10O2 C9H10O2 C9H10O3

3-(2-Nitrophenyl)  propanoic acid

2-Ethylbenzimidazole 3,5-Dimethylbenzoic acid Benzenepropanoic acid α-Methylbenzeneacetic acid α-Hydroxy-α-methyl  benezeneacetic acid Methylclothiazide N-Allylaniline 1-Indanamine

C9H11Cl2N3O4S2 C9H11N C9H11N C9H11NO2 4-(Dimethylamino)  benzoic acid Ethyl 4-aminobenzoate C9H11NO2 L-Phenylalanine C9H11NO2 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

C9H21N C10H7NO2

Step 2 3

2,2,6,6-Tetramethyl  piperidine Nonylamine 8-Quinolinecarboxylic acid

1 2 3

1 2 1 2 1 2 3 1 2 3 4

1 2 1 2 1 2

1 2 3 1 2 3 1 2 1 2

t/°C 25 25 25 25

pKa 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

25 22

25 25 25 25 25 25 25 25 25 25 25 25 25

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

25 25 25 23 25

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

25 25

10.64 1.82

20 20 20

8-49 Mol. form. C10H8O C10H8O C10H9N C10H9N C10H9N C10H9N C10H9N C10H9NO C10H9NO C10H9NO2 C10H10O2 C10H10O2 C10H10O2 C10H12N2 C10H12N2O

Name 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

C10H12N2O5 C10H12N4O3 C10H12O

Dinoseb Dideoxyinosine

C10H12O2 C10H12O5 C10H13N5O4 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

C10H18O4

Sebacic acid

C10H19N C10H19N C10H21N C10H21N

Bornylamine Neobornylamine Butylcyclohexylamine

C11H8O2 C11H11N C11H12I3NO2 C11H12N2O2

1 2

1 2 1 2 1 2

1 2 3 4 1 2 3 4 1 2

1,2,2,6,6-Pentamethyl  piperidine Decylamine 1H-Perimidine 1-Naphthalenecarboxylic   acid 2-Naphthalenecarboxylic   acid Methyl-1-naphthylamine Iopanoic acid L-Tryptophan

t/°C 25 25 25 25 20 20 20 25 20 25 25 25 25 25 25

25

5,6,7,8-Tetrahydro-2  naphthalenol Benzenebutanoic acid Propyl 3,4,5-trihydroxy  benzoate Adenosine

C10H23N C11H8N2 C11H8O2

Step

1 2

pKa 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 4.62 9.12 10.48

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

25 25 25 25 25 10 10 25 25 25 25 25 25 25 25

25 25

Dissociation Constants of Organic Acids and Bases

8-50 Mol. form. C11H12N4O3S C11H13F3N2O3S C11H13NO3 C11H13N3O3S C11H14N2O

Name Sulfamethoxypyridazine Mefluidide Hydrastinine Sulfisoxazole Cytisine

C11H14O2 C11H14O2 C11H14O2 C11H16N2O2

2-tert-Butylbenzoic acid 3-tert-Butylbenzoic acid 4-tert-Butylbenzoic acid Pilocarpine

C11H16N4O4 C11H17N

Pentostatin

C11H17NO3 C11H17N3O8 C11H18ClNO3 C11H18N2O3 C11H25N C11H26NO2PS C12H6Cl4O2S C12H8N2 C12H8N2 C12H10O C12H10O C12H10O C12H11N C12H11N C12H11N C12H11N C12H11N C12H11N3 C12H12N2

1,10-Phenanthroline Phenazine 2-Hydroxybiphenyl 3-Hydroxybiphenyl 4-Hydroxybiphenyl Diphenylamine 2-Aminobiphenyl 3-Aminobiphenyl 4-Aminobiphenyl 2-Benzylpyridine 4-Aminoazobenzene p-Benzidine

C12H12N2O3

Phenobarbital

C12H13N

1 2

1 2

Iocetamic acid

C12H14N4O2S C12H14N4O3S C12H17N3O4

Sulfacytine Agaritine

C12H20N2O2 C12H21N5O2S2

Aspergillic acid Nizatidine

C12H22O11 C12H22O11 C12H23N C12H27N C13H9N C13H9N C13H10N2 C13H10N2

Sucrose α-Maltose Dicyclohexylamine Dodecylamine Acridine Phenanthridine 9-Acridinamine 2-Phenylbenzimidazole

25 25 25 25 25

25 25 25

1 2

1 2 1 2

25 20 25 25 25 25 25 18 18 25 25 20 20

25

N,N-Dimethyl-1  naphthylamine N,N-Dimethyl-2  naphthylamine Sulfamethazine

t/°C

25

N,N-Diethyl-2-methyl  aniline Isoproterenol Tetrodotoxin Methoxamine hydrochloride Amobarbital Undecylamine Methylphosphonothioic acid   S[2-[bis(1-isopropyl)amino]  ethyl], O-ethylester Bithionol

C12H13I3N2O3 C12H13N

Step

25 1 2 1 2 1 2

1 2

25 21 25 20 20 20 25 25

pKa 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 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

Mol. form. C13H10O2 C13H10O3 C13H10O3 C13H10O3 C13H11N3 C13H12Cl2O4 C13H12N2O C13H12N2O3S C13H13N C13H14N2O13 C13H15N3O3 C13H16ClNO C13H19NO4S C13H21N C13H29N C14H12F3NO4S2 C14H12O2 C14H12O3

Name 2-Phenylbenzoic acid 2-Phenoxybenzoic acid 3-Phenoxybenzoic acid 4-Phenoxybenzoic acid 3,6-Acridinediamine Ethacrynic acid Harmine Sulfabenzamide 4-Benzylaniline Harmaline Imazapyr Ketamine

Step

25 25 1 2

4-[(Dipropylamino)  sulfonyl]benzoic acid 2,6-Di-tert-butylpyridine (Tridecyl)amine Perfluidone α-Phenylbenzeneacetic acid

C14H18N4O3 C14H19NO2 C14H21N3O3S C14H22N2O3 C14H31N C15H10ClN3O3

α-Hydroxy-α-phenyl  benezeneacetic acid Trimethoprim Methylphenidate Tolazamide Atenolol Tetradecylamine Clonazepam

C15H11I4NO4

L-Thyroxine

C15H14O3 C15H15NO2 C15H15N3O2

Fenoprofen Mefenamic acid Methyl Red

C15H17ClN4 C15H19NO2 C15H19N3O3

NeutralRed Tropacocaine Imazethapyr

C15H21N3O2

Physostigmine

C15H26N2

Sparteine

C15H33N C16H13ClN2O C16H14ClN3O C16H16N2O2

Pentadecylamine Valium Chlorodiazepoxide Lysergic acid

C16H17N3O4S

Cephalexin

C16H19N3O4S

Cephradine

C16H22N2

Lycodine

C16H35N C17H17NO2

Hexadecylamine Apomorphine

C17H19NO3 C17H19NO3

Piperine Morphine

C17H20N4O6

Riboflavin

t/°C 25 25 25 25 20

25 25 25

25

1 2 1 2 3

25

25 25 25

1 2

1 2 1 2 1 2

1 2 1 2 1 2 1 2 1 2 1 2 1

15

20 20 25

25

18 25 20

pKa 3.46 3.53 3.95 4.57 9.65 3.50 7.70 4.57 2.17 4.2 1.9 3.6 7.5 5.8 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 4.5 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

Dissociation Constants of Organic Acids and Bases Mol. form.

Name

C17H20O6 C17H23NO3 C17H27NO4 C18H19ClN4

Mycophenolic acid Hyoscyamine Nadolol Clozapine

C18H21NO3 C18H21N3O C18H32O2 C18H33ClN2O5S C18H39N C19H10Br4O5S C19H14O5S C19H16ClNO4 C19H17N3O4S2 C19H20N2O2 C19H21N C19H21NO3 C19H22N2O

Codeine Dibenzepin Linoleic acid Clindamycin Octadecylamine Bromophenol Blue Phenol Red Indomethacin Cephaloridine Phenylbutazone Protriptyline Thebaine Cinchonine

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

Hydroquinine Bromocresol Green Bromocresol Purple CresolRed Hydrastine Strychnine

Step 2

t/°C 25 21

1 2

25 25

1 2 1 2

15

25

1 2 3 1 2 1 2

25 25 20 20

25

pKa 9.69 4.5 9.7 9.67 3.70 7.60 8.21 8.25 4.77 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

8-51 Mol. form. C21H23ClFNO2 C21H31NO4 C21H35N3O7

Name 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

C30H23BrO4 C30H48O3 C31H36N2O11

Bromadiolone Oleanolic acid Novobiocin

C32H32O13S C33H40N2O9 C34H47NO11 C36H51NO11 C37H67NO13 C43H58N4O12

Teniposide Reserpine Aconitine Veratridine Erythromycin Rifampin

C45H73NO15 C46H56N4O10 C46H58N4O9

Solanine Vincristine Vinblastine

Step

t/°C

1 2 3 4

1 2 1 2

1 2

20

20 20 25

21

1 2

1 2

1 2

15

pKa 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 5.15 4.98 6.56 9.52 4.4 1.4 7.0 8.6 9.8 5.77 6.64 4.04 2.52 4.3 9.1 10.13 6.6 5.88 9.54 8.8 1.7 7.9 6.66 5.4 5.4 7.4