University:
California State University, Northridge
Course:
CHEM 101 | General Chemistry I
Academic year:

2023
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436

Pages:

9
Author:

Gloria R.

harxxxxx_App-G.qxd 3/8/10 1:34 PM Page AP11 APPE N DIX G Acid Dissociation Constants Ionic strength (␮) ⴝ 0 Name Structure* Acetic acid (ethanoic acid) CH3CO2H pKa† ␮ 0.1 M§ Ka‡ pKa† 4.756 1.75 105 4.56 2.344 (CO2H) 9.868 (NH3) 4.53 103 1.36 1010 2.33 9.71 4.601 2.51 105 4.64 3.232 5.86 104 3.01 2.08 (CO2H) 4.96 (NH3) 8.3 103 1.10 105 2.01 4.78 NH3 Alanine CHCH3 CO2H NH3 Aminobenzene (aniline) 4-Aminobenzenesulfonic acid (sulfanilic acid) NH3 O3S NH3 2-Aminobenzoic acid (anthranilic acid) CO2H 2-Aminoethanethiol (2-mercaptoethylamine) HSCH2CH2NH3 2-Aminoethanol (ethanolamine) HOCH2CH2NH3 —— —— 9.498 3.18 1010 9.52 4.70 (NH3) (20°) 9.97 (OH) (20°) 2.0 105 1.05 1010 4.74 9.87 9.245 5.69 1010 9.26 1.823 (CO2H) 8.991 (NH3) —— (NH2) 1.50 102 1.02 109 —— 2.03 9.00 (12.1) 2.24 6.96 (11.50) 5.8 103 1.10 107 3.2 1012 2.15 6.65 (11.18) 9.29 5.1 1010 9.14 OH 2-Aminophenol NH3 Ammonia NH4 NH3 Arginine NH2 CHCH2CH2CH2NHC NH2 CO2H O As Arsenic acid (hydrogen arsenate) HO Arsenious acid (hydrogen arsenite) As(OH)3 OH NH3 Asparagine OH 8.21 (SH) 10.73 (NH3) O CHCH2CNH2 CO2H —— —— —— —— 2.16 (CO2H) 8.73 (NH3) *Each acid is written in its protonated form. The acidic protons are indicated in bold type. † pKa values refer to 25⬚C unless otherwise indicated. Values in parentheses are considered to be less reliable. ‡ The accurate way to calculate Kb for the conjugate base is pKb 13.995 pKa and Kb 10pKb. § See marginal note on page 166 for distinction between pKa at ␮ 0 and at ␮ 0.1 M. (Continued) APPENDIX G Acid Dissociation Constants AP11 harxxxxx_App-G.qxd 2/15/10 5:25 PM Page AP12 Ionic strength (␮) ⴝ 0 Name Structure pKa NH3 Aspartic acid CHCH2CO2H CO2H Aziridine (dimethyleneimine) Benzene-1,2,3-tricarboxylic acid (hemimellitic acid) NH2 CO2H CO2H ␮ 0.1 M Ka pKa 1.02 102 1.26 104 9.95 1011 1.95 3.71 9.96 8.04 9.1 109 —— 2.86 4.30 6.28 1.38 103 5.0 105 5.2 107 2.67 3.91 5.50 6.28 105 4.01 1.990 (-CO2H) 3.900 ( -CO2H) 10.002 (NH3) CO2H Benzoic acid CO2H 4.202 Benzylamine CH2NH3 9.35 4.5 1010 9.40 —— 4.34 —— 4.6 105 (1.3) 4.41 5.79 1010 1.82 1013 1.58 1014 8.98 —— —— 1.25 103 2.71 2,2-Bipyridine N N H H 9.237 (12.74) (20°) (13.80) (20°) Boric acid (hydrogen borate) B(OH)3 Bromoacetic acid BrCH2CO2H Butane-2,3-dione dioxime (dimethylglyoxime) Butanoic acid cis-Butenedioic acid (maleic acid) trans-Butenedioic acid (fumaric acid) Butylamine NOH HON CH3 CH3 CH3CH2CH2CO2H CO2H CO2H CO2H HO2C CH3CH2CH2CH2NH3 O 2.902 10.66 (12.0) 2.2 1011 1 1012 10.45 (11.9) 4.818 1.52 105 4.62 1.92 6.27 1.20 102 5.37 107 1.75 5.84 3.02 4.48 9.5 104 3.3 105 2.84 4.09 10.640 2.29 1011 10.66 6.351 10.329 4.46 107 4.69 1011 6.13 9.91 Carbonic acid* (hydrogen carbonate) HO Chloroacetic acid ClCH2CO2H 2.865 1.36 103 2.69 3-Chloropropanoic acid ClCH2CH2CO2H 4.11 7.8 105 3.92 Chlorous acid (hydrogen chlorite) HOCl£O 1.96 1.10 102 —— C OH *The concentration of “carbonic acid” is considered to be the sum [H2CO3] [CO2(aq)]. See Box 6-4. AP12 APPENDIX G Acid Dissociation Constants harxxxxx_App-G.qxd 2/15/10 5:25 PM Page AP13 Ionic strength (␮) ⴝ 0 Name Structure pKa ␮ 0.1 M Ka pKa O Chromic acid (hydrogen chromate) Citric acid (2-hydroxypropane-1,2,3tricarboxylic acid) Cr HO OH O CO2H HO2CCH2CCH2CO2H (0.2) (20°) 6.51 1.6 3.1 107 3.128 4.761 6.396 7.44 104 1.73 105 4.02 107 (0.6) (20 C) 6.05 2.90 4.35 5.70 OH Cyanoacetic acid NCCH2CO2H 2.472 3.37 103 Cyclohexylamine NH3 10.567 2.71 1011 10.62 (1.7) (CO2H) 8.36 (SH) 10.74 (NH3) 2 102 4.4 109 1.82 1011 (1.90) 8.18 10.30 Cysteine NH3 CHCH2SH —— CO2H Dichloroacetic acid Cl2CHCO2H (1.1) 8 102 (0.9) Diethylamine (CH3CH2)2NH2 11.00 1.0 1011 11.04 9.45 —— 3.5 1010 —— 9.26 (13.3) —— —— —— —— 9.30 11.06 3.036 4.366 9.20 104 4.31 105 2.82 3.97 —— —— —— —— 8.63 10.65 10.774 1.68 1011 10.81 4.114 7.69 105 3.92 OH 1,2-Dihydroxybenzene (catechol) OH OH 1,3-Dihydroxybenzene (resorcinol) OH OH D-2,3-Dihydroxybutanedioic acid (D-tartaric acid) 2,3-Dimercaptopropanol HO2CCHCHCO2H OH HOCH2CHCH2SH SH Dimethylamine (CH3)2NH2 NO2 2,4-Dinitrophenol O2N OH Ethane-1,2-dithiol HSCH2CH2SH —— —— —— —— Ethylamine CH3CH2NH3 10.673 2.12 1011 10.69 Ethylenediamine (1,2-diaminoethane) H3NCH2CH2NH3 6.848 9.928 1.42 107 1.18 1010 7.11 9.92 8.85 (30 C) 10.43 (30 C) (Continued) APPENDIX G Acid Dissociation Constants AP13 harxxxxx_App-G.qxd 2/15/10 5:25 PM Page AP14 Ionic strength (␮) ⴝ 0 Name Structure pKa Ethylenedinitrilotetraacetic acid (EDTA) (HO2CCH2)2NHCH2CH2NH(CH2CO2H)2 —— (CO2H) —— (CO2H) —— (CO2H) —— (CO2H) 6.273 (NH) 10.948 (NH) Formic acid (methanoic acid) HCO2H NH3 Glutamic acid CHCH2CH2CO2H CO2H NH3 Glutamine ␮ 0.1 M Ka pKa —— —— —— —— 5.3 107 1.13 1011 (0.0) (CO2H) ( 1 M) (1.5) (CO2H) 2.00 (CO2H) 2.69 (CO2H) 6.13 (NH) 10.37 (NH) 3.744 1.80 104 3.57 2.160 (-CO2H) 4.30 ( -CO2H) 9.96 (NH3) 6.92 103 5.0 105 1.10 1010 2.16 4.15 9.58 O CHCH2CH2CNH2 CO2H —— —— —— —— 2.19 (CO2H) 9.00 (NH3) NH3 Glycine (aminoacetic acid) Guanidine 1,6-Hexanedioic acid (adipic acid) Hexane-2,4-dione CH2 2.350 (CO2H) 9.778 (NH3) CO2H NH 2 H2N C NH2 HO2CCH2CH2CH2CH2CO2H O O CH3CCH2CCH2CH3 NH3 Histidine NH CHCH2 N H CO2H Hydrazine H3N NH3 Hydrazoic acid (hydrogen azide) HN Hydrogen cyanate HOCΩN N N —— 4.424 5.420 9.38 (1.6) (CO2H) 5.97 (NH) 9.28 (NH3) 4.47 103 1.67 1010 2.33 9.57 (13.5) ( 1 M) —— 3.77 105 3.80 106 4.2 1010 3 102 1.07 106 5.2 1010 4.26 5.04 9.11 (20 C) (1.7) 6.05 9.10 0.99 7.98 1.0 101 1.05 108 4.65 2.2 105 4.45 3.48 3.3 104 —— 10 (0.21) ( 0.5 M) 8.07 Hydrogen cyanide HCΩN 9.21 6.2 10 Hydrogen fluoride HF 3.17 6.8 104 2.94 Hydrogen peroxide HOOH 11.65 2.2 1012 —— Hydrogen sulfide H2S Hydrogen thiocyanate HSCΩN Hydroxyacetic acid (glycolic acid) AP14 HOCH2CO2H 7.02 14.0* (1.1) (20°C) 3.832 8 9.04 9.5 10 1.0 1014* 6.82 —— 1.3 101 —— 4 1.48 10 3.62 APPENDIX G Acid Dissociation Constants harxxxxx_App-G.qxd 2/15/10 5:25 PM Page AP15 Ionic strength (␮) ⴝ 0 Name Structure Hydroxybenzene (phenol) OH CO2H 2-Hydroxybenzoic acid (salicylic acid) L-Hydroxybutanedioic pKa OH OH acid (malic acid) Hydroxylamine 8-Hydroxyquinoline (oxine) HO2CCH2CHCO2H 9.997 2.972 (CO2H) (13.7) (OH) N H HO Ka pKa 1.01 1010 9.78 1.07 103 2 1014 2.80 (13.4) 3.48 104 8.00 106 3.24 4.68 5.96 (NH) (13.74) (OH) 1.10 106 1.8 1014 5.96 —— 4.94 (NH) 9.82 (OH) 1.15 105 1.51 1010 4.97 9.65 3.459 5.097 HONH3 ␮ 0.1 M Hypobromous acid (hydrogen hypobromite) HOBr 8.63 2.3 109 —— Hypochlorous acid (hydrogen hypochlorite) HOCl 7.53 3.0 108 —— Hypoiodous acid (hydrogen hypoiodite) HOI 10.64 2.3 1011 —— (1.3) 5 102 Hypophosphorous acid (hydrogen hypophosphite) Imidazole (1,3-diazole) Iminodiacetic acid O (1.1) H2POH NH N H H2N(CH2CO2H)2 O 6.993 (14.5) (1.85) (CO2H) 2.84 (CO2H) 9.79 (NH2 ) 0.77 Iodic acid (hydrogen iodate) HOI Iodoacetic acid ICH2CO2H 1.02 107 3 1015 7.00 —— 1.41 102 1.45 103 1.62 1010 (1.77) 2.62 9.34 0.17 —— O 3.175 6.68 104 2.98 2.318 (CO2H) 9.758 (NH3) 4.81 103 1.75 1010 2.26 9.60 2.328 (CO2H) 9.744 (NH3) 4.70 103 1.80 1010 2.32 9.58 (1.77) (CO2H) 9.07 (-NH3) 10.82 ( -NH3) 1.7 102 8.5 1010 1.51 1011 2.15 9.15 10.66 NH3 Isoleucine CHCH(CH3)CH2CH3 CO2H NH3 Leucine CHCH2CH(CH3)2 CO2H NH 3 Lysine CHCH2CH2CH2CH2NH3 CO2H (Continued) APPENDIX G Acid Dissociation Constants AP15 harxxxxx_App-G.qxd 2/15/10 5:25 PM Page AP16 Ionic strength (␮) ⴝ 0 Name Structure pKa Malonic acid (propanedioic acid) HO2CCH2CO2H Mercaptoacetic acid (thioglycolic acid) HSCH2CO2H 2-Mercaptoethanol HSCH2CH2OH 2.847 5.696 3.64 (CO2H) 10.61 (SH) 9.72 ␮ 0.1 M Ka pKa 1.42 103 2.01 106 2.65 5.27 2.3 104 2.5 1011 3.48 10.11 1.9 1010 9.40 NH3 Methionine CHCH2CH2SCH3 CO2H OCH3 2-Methoxyaniline (o-anisidine) —— —— 2.18 (CO2H) 9.08 (NH3) 4.526 2.98 105 5.357 4.40 106 5.33 10.632 2.33 1011 10.65 4.447 3.57 105 —— 5.080 8.32 106 5.09 —— NH3 4-Methoxyaniline ( p-anisidine) CH3O Methylamine CH3NH3 NH3 CH3 2-Methylaniline (o-toluidine) 4-Methylaniline ( p-toluidine) —— —— NH3 CH3 NH3 CH3 2-Methylphenol (o-cresol) 10.31 4.9 1011 10.09 10.269 5.5 1011 10.04 OH 4-Methylphenol ( p-cresol) CH3 Morpholine (perhydro-1,4-oxazine) O OH NH2 8.492 3.22 109 —— 3.67 2.1 104 —— 4.16 6.9 105 —— 9.416 3.84 1010 9.14 9.573 2.67 1010 9.31 —— 0.010 1.15 103 4.63 1011 (1.0) 1.81 2.52 9.46 CO2H 1-Naphthoic acid CO2H 2-Naphthoic acid OH 1-Naphthol OH 2-Naphthol Nitrilotriacetic acid AP16 HN(CH2CO2H)3 —— (CO2H) 2.0 (CO2H) (25°) 2.940 (CO2H) (20°) 10.334 (NH) (20°) APPENDIX G Acid Dissociation Constants harxxxxx_App-G.qxd 2/15/10 10:24 PM Page AP17 Ionic strength (␮) ⴝ 0 Name Structure ␮ ⫽ 0.1 M pKa Ka 2.185 6.53 ⫻ 10⫺3 —— 3.449 3.56 ⫻ 10⫺4 3.28 3.442 3.61 ⫻ 10⫺4 3.28 8.57 2.7 ⫻ 10⫺9 —— 7.230 5.89 ⫻ 10⫺8 7.04 8.37 4.3 ⫻ 10⫺9 8.16 7.149 7.10 ⫻ 10⫺8 6.96 pKa NO2 2-Nitrobenzoic acid CO2H NO2 3-Nitrobenzoic acid CO2H 4-Nitrobenzoic acid O2N CO2H Nitroethane CH3CH2NO2 NO2 2-Nitrophenol OH NO2 3-Nitrophenol OH 4-Nitrophenol O2N N-Nitrosophenylhydroxylamine (cupferron) OH NO N OH —— —— 4.16 Nitrous acid HON£O 3.15 7.1 ⫻ 10⫺4 —— Oxalic acid (ethanedioic acid) HO2CCO2H 1.250 4.266 5.62 ⫻ 10⫺2 5.42 ⫻ 10⫺5 (1.2) 3.80 3.46 3.5 ⫻ 10⫺4 3.05 2.56 4.37 2.8 ⫻ 10⫺3 4.3 ⫻ 10⫺5 2.26 3.90 Oxoacetic acid (glyoxylic acid) Oxobutanedioic acid (oxaloacetic acid) 2-Oxopentanedioic (␣-ketoglutaric acid) 2-Oxopropanoic acid (pyruvic acid) O HCCO2H O HO2CCH2CCO2H O HO2CCH2CH2CCO2H O —— —— —— —— (1.9) (␮ ⫽ 0.5 M) 4.44 (␮ ⫽ 0.5 M) 2.48 3.3 ⫻ 10⫺3 2.26 CH3CCO2H 1,5-Pentanedioic acid (glutaric acid) HO2CCH2CH2CH2CO2H 4.345 5.422 4.52 ⫻ 10⫺5 3.78 ⫻ 10⫺6 4.19 5.06 Pentanoic acid (valeric acid) CH3CH2CH2CH2CO2H 4.843 1.44 ⫻ 10⫺5 4.63 (18⬚C) 1,10-Phenanthroline NH HN ⫹ Phenylacetic acid —— 4.91 ⫹ CH2CO2H 4.310 —— 1.23 ⫻ 10⫺5 (1.8) 4.92 4.90 ⫻ 10⫺5 4.11 (Continued) APPENDIX G Acid Dissociation Constants AP17 harxxxxx_App-G.qxd 2/15/10 5:25 PM Page AP18 Ionic strength (␮) ⴝ 0 Name Structure pKa ␮ 0.1 M Ka pKa NH3 Phenylalanine CO2H O Phosphoric acid* (hydrogen phosphate) P HO 6.3 103 4.9 1010 2.18 9.09 2.148 7.198 12.375 7.11 103 6.34 108 4.22 1013 1.92 6.71 11.52 (1.5) 6.78 3 102 1.66 107 —— —— 2.950 5.408 1.12 103 3.90 106 2.76 4.92 5.333 9.731 4.65 106 1.86 1010 5.64 9.74 11.125 7.50 1012 11.08 1.952 (CO2H) 10.640 (NH2 ) 1.12 102 2.29 1011 1.89 10.46 2.20 (CO2H) 9.31 (NH3) CHCH2 OH OH O Phosphorous acid (hydrogen phosphite) HP OH OH CO2H Phthalic acid (benzene-1,2-dicarboxylic acid) Piperazine (perhydro-1,4-diazine) CO2H NH2 NH2 Piperidine Proline H2N CO2H N H2 Propanoic acid CH3CH2CO2H 4.874 1.34 105 4.69 Propenoic acid (acrylic acid) H2C£CHCO2H 4.258 5.52 105 —— Propylamine CH3CH2CH2NH3 10.566 2.72 1011 10.64 5.20 6.3 106 5.24 (1.01) (CO2H) 5.39 (NH) 9.8 102 4.1 106 (0.95) 5.21 2.03 (CO2H) 4.82 (NH) 9.3 103 1.51 105 2.08 4.69 —— —— —— —— —— —— —— —— Pyridine (azine) NH NH Pyridine-2-carboxylic acid (picolinic acid) Pyridine-3-carboxylic acid (nicotinic acid) CO2H HO2C NH O Pyridoxal-5-phosphate HO O POCH2 HO Pyrophosphoric acid (hydrogen diphosphate) AP18 O O (HO)2POP(OH)2 CH OH N H CH3 (0.9) 2.28 6.70 9.40 0.13 5.2 103 2.0 107 4.0 1010 (1.4) (POH) 3.51 (OH) 6.04 (POH) 8.25 (NH) (0.8) (1.9) 5.94 8.25 APPENDIX G Acid Dissociation Constants harxxxxx_App-G.qxd 2/15/10 5:25 PM Page AP19 Ionic strength (␮) ⴝ 0 Name Structure pKa NH2 Pyrrolidine 11.305 ␮ 0.1 M Ka pKa 12 4.95 10 11.3 NH3 Serine CHCH2OH CO2H Succinic acid (butanedioic acid) HO2CCH2CH2CO2H 2.187 (CO2H) 9.209 (NH3) 6.50 103 6.18 1010 2.16 9.05 4.207 5.636 6.21 105 2.31 106 3.99 5.24 1.987 (pK2 ) 1.03 102 1.54 1.857 7.172 1.39 102 6.73 108 1.66 6.85 O Sulfuric acid (hydrogen sulfate) Sulfurous acid (hydrogen sulfite) HO S OH O O HOSOH O Thiosulfuric acid (hydrogen thiosulfate) (0.6) (1.6) HOSSH 0.3 0.03 —— (1.3) O NH3 Threonine CHCHOHCH3 2.088 (CO2H) 9.100 (NH3) CO2H Trichloroacetic acid Triethanolamine Triethylamine 1,2,3-Trihydroxybenzene (pyrogallol) Cl3CCO2H (0.5) (HOCH2CH2)3NH (CH3CH2)3NH 7.762 10.72 OH —— —— —— OH OH 8.17 103 7.94 1010 3 2.20 8.94 —— 8 1.73 10 11 1.9 10 —— —— —— 7.85 10.76 8.96 11.00 (14.0) (20 C) Trimethylamine (CH3)3NH 9.799 1.59 1010 9.82 Tris(hydroxymethyl)aminomethane (tris or tham) (HOCH2)3CNH3 8.072 8.47 109 8.10 NH3 Tryptophan CHCH2 CO2H N H NH3 Tyrosine CHCH2 CO2H OH —— —— —— —— 2.37 (CO2H) 9.33 (NH3) —— —— —— —— —— —— 2.41 (CO2H) 8.67 (NH3) 11.01 (OH) NH3 Valine CHCH(CH3)2 CO2H Water* H2O 2.286 (CO2H) 9.719 (NH3) 13.997 5.18 103 1.91 1010 2.27 9.52 1.01 1014 —— *The constant given for water is Kw. APPENDIX G Acid Dissociation Constants AP19