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Formula pK sp K sp Formula pK sp K sp
Azides: L 5 N23 Chromates: L 5 CrO22
4
CuL 8.31 4.9 3 1029 BaL 9.67 2.1 3 10210
AgL 8.56 2.8 3 1029 CuL 5.44 3.6 3 1026
Hg2L2 9.15 7.1 3 10210 Ag2L 11.92 1.2 3 10212
TlL 3.66 2.2 3 1024 Hg2L 8.70 2.0 3 1029
PdL2(a) 8.57 2.7 3 1029 Tl2L 12.01 9.8 3 10213
*The designations a, b, or g after some formulas refer to particular crystalline forms (which are customarily identified by Greek
letters). Data for salts except oxalates are taken mainly from A. E. Martell and R. M. Smith, Critical Stability Constants, Vol. 4
(New York: Plenum Press, 1976). Data for oxalates are from L. G. Sillén and A. E. Martell, Stability Constants of Metal-Ion
Complexes, Supplement No. 1 (London: The Chemical Society, Special Publication No. 25, 1971). Another source: R. M. H. Verbeeck
et al., Inorg. Chem. 1984, 23, 1922.
Conditions are 258C and zero ionic strength unless otherwise indicated: (a) 198C; (b) 208C; (c) 388C; (d) 0.1 M; (e) 0.2 M; (f) 0.5 M;
(g) 1 M; (h) 3 M; (i) 4 M; (j) 5 M.
(Continued)
NH⫹3
4-Aminobenzenesulfonic acid ⫺O S
3
NH⫹3 3.232 5.86 3 1024 3.01
(sulfanilic acid)
NH⫹3
2-Aminobenzoic acid 2.08 (CO2H) 8.3 3 1023 2.01
(anthranilic acid) CO2H 4.96 (NH3) 1.10 3 1025 4.78
1
2-Aminoethanethiol HSCH2CH2NH3 —— 8.21 (SH)
(2-mercaptoethylamine) —— 10.73 (NH3)
1
2-Aminoethanol HOCH2CH2NH3 9.498 3.18 3 10210 9.52
(ethanolamine)
OH
4.70 (NH3) (20°) 2.0 3 1025 4.74
2-Aminophenol
9.97 (OH) (20°) 1.05 3 10210 9.87
NH⫹3
1
Ammonia NH4 9.245 5.69 3 10210 9.26
NH⫹3
NH⫹2 1.823 (CO2H) 1.50 3 1022 2.03
Arginine CHCH2CH2CH2NHC 8.991 (NH3) 1.02 3 1029 9.00
NH2 —— (NH2) —— (12.1)
CO2H
O
2.24 5.8 3 1023 2.15
Arsenic acid HO As OH 6.96 1.10 3 1027 6.65
(hydrogen arsenate) (11.50) 3.2 3 10212 (11.18)
OH
NH⫹3 O
*Each acid is written in its protonated form. The acidic protons are indicated in bold type.
†
pKa values refer to 258C unless otherwise indicated. Values in parentheses are considered to be less reliable. Data are from
A. E. Martell, R. M. Smith, and R. J. Motekaitis, NIST Database 46 (Gaithersburg, MD: National Institute of Standards and
Technology, 2001).
‡
The accurate way to calculate Kb for the conjugate base is pKb 5 13.995 2 pKa and Kb 5 102pKb.
§
See marginal note on page 191 for distinction between pKa at 5 0 and at 5 0.1 M.
(Continued)
NH⫹3
 1.990 (a-CO2H) 1.02 3 1022 1.95
Aspartic acid CHCH2CO2H 3.900 (b-CO2H) 1.26 3 1024 3.71
10.002 (NH3) 9.95 3 10211 9.96
␣ CO2H
—— —— (1.3)
2,29-Bipyridine 4.34 4.6 3 1025 4.41
N⫹ ⫹N
H H
HON NOH
Butane-2,3-dione dioxime 10.66 2.2 3 10211 10.45
(dimethylglyoxime) CH3 CH3 (12.0) 1 3 10212 (11.9)
CO2H
cis-Butenedioic acid 1.92 1.20 3 1022 1.75
(maleic acid) CO2H 6.27 5.37 3 1027 5.84
CO2H
trans-Butenedioic acid 3.02 9.5 3 1024 2.84
(fumaric acid) 4.48 3.3 3 1025 4.09
HO2C
1
Butylamine CH3CH2CH2CH2NH3 10.640 2.29 3 10211 10.66
O
Carbonic acid* 6.351 4.46 3 1027 6.13
(hydrogen carbonate) HO C OH 10.329 4.69 3 10211 9.91
*The concentration of “carbonic acid” is considered to be the sum [H2CO3] 1 [CO2(aq)]. See Box 6-4.
1
Diethylamine (CH3CH2)2NH2 11.00 1.0 3 10211 11.04
OH
1,2-Dihydroxybenzene 9.45 3.5 3 10210 9.26
(catechol) —— —— (13.3)
OH
OH
1,3-Dihydroxybenzene —— —— 9.30
(resorcinol) —— —— 11.06
OH
OH
HOCH2CHCH2SH
2,3-Dimercaptopropanol —— —— 8.63
SH —— —— 10.65
NO2
2,4-Dinitrophenol 4.114 7.69 3 1025 3.92
O2N OH
(Continued)
NH⫹3
␥ 2.160 (a-CO2H) 6.92 3 1023 2.16
Glutamic acid CHCH2CH2CO2H 4.30 (g-CO2H) 5.0 3 1025 4.15
9.96 (NH3) 1.10 3 10210 9.58
␣ CO2H
NH⫹3 O
Glutamine CHCH2CH2CNH2 —— —— 2.19 (CO2H)
—— —— 9.00 (NH3)
CO2H
NH⫹3
⫹NH
2
Guanidine —— —— (13.5) (m 5 1 M)
H2N C NH2
O O
Hexane-2,4-dione 9.38 4.2 3 10210 9.11 (208C)
CH3CCH2CCH2CH3
NH⫹3
NH ( 1.6) (CO2H) 3 3 1022 (1.7)
Histidine CHCH2 ⫹ 5.97 (NH) 1.07 3 1026 6.05
N 9.28 (NH3) 5.2 3 10210 9.10
CO2H H
1 1
Hydrazine H3N 2 NH3 20.99 1.0 3 101 (20.21) (m 5 0.5 M)
7.98 1.05 3 1028 8.07
⫹ ⫺
Hydrazoic acid HN N N 4.65 2.2 3 1025 4.45
(hydrogen azide)
CO2H
2-Hydroxybenzoic acid 2.972 (CO2H) 1.07 3 1023 2.80
(salicylic acid) (13.7) (OH) 2 3 10214 (13.4)
OH
OH
l-Hydroxybutanedioic acid 3.459 3.48 3 1024 3.24
(malic acid) HO2CCH2CHCO2H 5.097 8.00 3 1026 4.68
1
Hydroxylamine HONH3 5.96 (NH) 1.10 3 1026 5.96
(13.74) (OH) 1.8 3 10214 ——
O
Hypophosphorous acid (1.3) 5 3 1022 (1.1)
(hydrogen hypophosphite) H2POH
⫹
(1.85) (CO2H) 1.41 3 1022 (1.77)
Iminodiacetic acid H2N(CH2CO2H)2 2.84 (CO2H) 1.45 3 1023 2.62
9.79 (NH2 ) 1.62 3 10210 9.34
O
Iodic acid 0.77 0.17 ——
(hydrogen iodate) HOI O
NH⫹3
Isoleucine CHCH(CH3)CH2CH3 2.318 (CO2H) 4.81 3 1023 2.26
9.758 (NH3) 1.75 3 10210 9.60
CO2H
NH⫹3
Leucine CHCH2CH(CH3)2 2.328 (CO2H) 4.70 3 1023 2.32
9.744 (NH3) 1.80 3 10210 9.58
CO2H
␣ NH⫹
3
⑀ (1.77) (CO2H) 1.7 3 1022 2.15
Lysine CHCH2CH2CH2CH2NH⫹3 9.07 (a-NH3) 8.5 3 10210 9.15
10.82 (e-NH3) 1.51 3 10211 10.66
CO2H
(Continued)
NH⫹3
Methionine CHCH2CH2SCH3 —— —— 2.18 (CO2H)
—— —— 9.08 (NH3)
CO2H
OCH3
2-Methoxyaniline 4.526 2.98 3 1025 ——
(o-anisidine) ⫹
NH3
CH3
2-Methylaniline 4.447 3.57 3 1025 ——
(o-toluidine) ⫹
NH3
⫹
4-Methylaniline CH3 NH3 5.080 8.32 3 1026 5.09
( p-toluidine)
CH3
2-Methylphenol 10.31 4.9 3 10211 10.09
(o-cresol)
OH
CO2H
1-Naphthoic acid 3.67 2.1 3 1024 ——
CO2H
2-Naphthoic acid 4.16 6.9 3 1025 ——
OH
1-Naphthol 9.416 3.84 3 10210 9.14
OH
2-Naphthol 9.573 2.67 3 10210 9.31
—— (CO2H) —— (1.0)
⫹ 2.0 (CO2H) (25°) 0.010 1.81
Nitrilotriacetic acid HN(CH2CO2H)3 2.940 (CO2H) (20°) 1.15 3 1023 2.52
10.334 (NH) (20°) 4.63 3 10211 9.46
NO2
2-Nitrobenzoic acid 2.185 6.53 3 1023 ——
CO2H
NO2
NO2
2-Nitrophenol 7.230 5.89 3 1028 7.04
OH
NO2
NO
N-Nitrosophenylhydroxylamine N —— —— 4.16
(cupferron) OH
O
Oxoacetic acid 3.46 3.5 3 1024 3.05
(glyoxylic acid) HCCO2H
O
Oxobutanedioic acid 2.56 2.8 3 1023 2.26
(oxaloacetic acid) HO2CCH2CCO2H 4.37 4.3 3 1025 3.90
O
2-Oxopentanedioic —— —— (1.9) (m 5 0.5 M)
(a-ketoglutaric acid) HO2CCH2CH2CCO2H —— —— 4.44 (m 5 0.5 M)
O
2-Oxopropanoic acid 2.48 3.3 3 1023 2.26
(pyruvic acid) CH3CCO2H
(Continued)
NH⫹3
O
2.148 7.11 3 1023 1.92
Phosphoric acid* HO P OH 7.198 6.34 3 1028 6.71
(hydrogen phosphate) 12.375 4.22 3 10213 11.52
OH
O
Phosphorous acid HP OH (1.5) 3 3 1022 ——
(hydrogen phosphite) 6.78 1.66 3 1027 ——
OH
CO2H
Phthalic acid 2.950 1.12 3 1023 2.76
(benzene-1,2-dicarboxylic acid)
CO2H 5.408 3.90 3 1026 4.92
⫹
Piperidine NH2 11.125 7.50 3 10212 11.08
NH⫹
Pyridine-2-carboxylic acid (1.01) (CO2H) 9.8 3 1022 (0.95)
(picolinic acid) CO2H 5.39 (NH) 4.1 3 1026 5.21
HO2C
Pyridine-3-carboxylic acid 2.03 (CO2H) 9.3 3 1023 2.08
(nicotinic acid) NH⫹ 4.82 (NH) 1.51 3 1025 4.69
O
O CH —— —— (1.4) (POH)
Pyridoxal-5-phosphate HO POCH2 OH —— —— 3.51 (OH)
—— —— 6.04 (POH)
HO N —— —— 8.25 (NH)
⫹ CH3
H
*pK3 from A. G. Miller and J. W. Macklin, Anal. Chem. 1983, 55, 684.
NH⫹3
Serine CHCH2OH 2.187 (CO2H) 6.50 3 1023 2.16
9.209 (NH3) 6.18 3 10210 9.05
CO2H
O
Sulfurous acid 1.857 1.39 3 1022 1.66
(hydrogen sulfite) HOSOH 7.172 6.73 3 1028 6.85
O
Thiosulfuric acid (0.6) 0.3 ——
(hydrogen thiosulfate) HOSSH (1.6) 0.03 (1.3)
O
NH⫹3
Threonine CHCHOHCH3 2.088 (CO2H) 8.17 3 1023 2.20
9.100 (NH3) 7.94 3 10210 8.94
CO2H
OH
1,2,3-Trihydroxybenzene OH —— —— 8.96
(pyrogallol) —— —— 11.00
OH —— —— (14.0) (208C)
NH⫹3
Tryptophan CHCH2 —— —— 2.37 (CO2H)
—— —— 9.33 (NH3)
CO2H N
H
NH⫹3
—— —— 2.41 (CO2H)
Tyrosine CHCH2 OH —— —— 8.67 (NH3)
—— —— 11.01 (OH)
CO2H
NH⫹3
Valine CHCH(CH3)2 2.286 (CO2H) 5.18 3 1023 2.27
9.719 (NH3) 1.91 3 10210 9.52
CO2H
*All species are aqueous unless otherwise indicated. The reference state for amalgams is an infinitely dilute solution of the element in
Hg. The temperature coefficient, dE8/dT, allows us to calculate the standard potential, E8(T), at temperature T: E8(T) 5 E8 1 (dE8/dT)DT,
where DT is T 2 298.15 K. Note the units mV/K for dE8/dT. Once you know E8 for a net cell reaction at temperature T, you can
find the equilibrium constant, K, for the reaction from the formula K 5 10nFE°/RT ln 10, where n is the number of electrons in each
half-reaction, F is the Faraday constant, and R is the gas constant.
SOURCES: The most authoritative source is S. G. Bratsch, J. Phys. Chem. Ref. Data 1989, 18, 1. Additional data come from L. G.
Sillén and A. E. Martell, Stability Constants of Metal-Ion Complexes (London: The Chemical Society, Special Publications Nos. 17
and 25. 1964 and 1971); G. Milazzo and S. Caroli, Tables of Standard Electrode Potentials (New York: Wiley, 1978); T. Mussini, P.
Longhi, and S. Rondinini, Pure Appl. Chem. 1985, 57, 169. Another good source is A. J. Bard, R. Parsons, and J. Jordan. Standard
Potentials in Aqueous Solution (New York: Marcel Dekker, 1985). Reduction potentials for 1 200 free radical reactions are given by
P. Wardman, J. Phys. Chem. Ref. Data 1989, 18, 1637.
14243
1.70 1 F HClO4
Ce41 1 e2 T Ce31 1.44 1 F H2SO4
1.61 1 F HNO3
1.47 1 F HCl
Ce31 1 3e2 T Ce(s) 22.336 0.280
Cesium
Cs1 1 e2 1 Hg T Cs(in Hg) 21.950
Cs1 1 e2 T Cs(s) 23.026 21.172
Chlorine
HClO2 1 2H1 1 2e2 T HOCl 1 H2O 1.674 0.55
HClO 1 H1 1 e2 T 12Cl2(g) 1 H2O 1.630 20.27
1
ClO2 1 2
3 1 6H 1 5e T 2 Cl2(g) 1 3H2O 1.458 20.347
2T 2
Cl2(aq) 1 2e 2Cl 1.396 20.72
Cl2(g) 1 2e2 T 2Cl2 1.360 4 21.248
ClO2 1 2 2
4 1 2H 1 2e T ClO3 1 H2O 1.226 20.416
2 1 2T
ClO3 1 3H 1 2e HClO2 1 H2O 1.157 20.180
ClO2 1 2
3 1 2H 1 e T ClO2 1 H2O 1.130 0.074
ClO2 1 e2 T ClO22 1.068 21.335
Chromium
Cr2O722 1 14H1 1 6e2 T 2Cr31 1 7H2O 1.36 21.32
CrO422 1 4H2O 1 3e2 T Cr(OH)3 (s, hydrated) 1 5OH2 20.12 21.62
Cr31 1 e2 T Cr21 20.42 1.4
Cr31 1 3e2 T Cr(s) 20.74 0.44
Cr21 1 2e2 T Cr(s) 20.89 20.04
Cobalt
1.92 1.23
123
(Continued)
0.771 1.175
0.732 1 F HCl
Fe31 1 e2 T Fe21 0.767 1 F HClO4
0.746 1 F HNO3
0.68 1 F H2SO4
(Continued)
(Continued)
0.77 1 F HCl
Tl31 1 2e2 T Tl1 1.22 1 F H2SO4
1.23 1 F HNO3
1.26 1 F HClO4
Tl1 1 e2 1 Hg T Tl(in Hg) 20.294
Tl1 1 e2 T Tl(s) 20.336 21.312
TlCl(s) 1 e2 T Tl(s) 1 Cl2 20.557
Thorium
Th41 1 4e2 T Th(s) 21.826 0.557
Thulium
Tm31 1 3e2 T Tm(s) 22.319 0.394
Tin
Sn(OH)1 1 2
3 1 3H 1 2e T Sn
21
1 3H2O 0.142
Sn41 1 2e2 T Sn21 0.139 1 F HCl
SnO2(s) 1 4H1 1 2e2 T Sn21 1 2H2O 20.094 20.31
Sn21 1 2e2 T Sn(s) 20.141 20.32
SnF 622 1 4e2 T Sn(s) 1 6F2 20.25
Sn(OH)622 1 2e2 T Sn(OH)2 3 1 3OH
2
20.93
2T
Sn(s) 1 4H2O 1 4e SnH4(g) 1 4OH2 21.316 21.057
SnO2(s) 1 H2O 1 2e2 T SnO(s) 1 2OH2 20.961 21.129
Titanium
TiO21 1 2H1 1 e2 T Ti31 1 H2O 0.1 20.6
Ti31 1 e2 T Ti21 20.9 1.5
TiO2(s) 1 4H1 1 4e2 T Ti(s) 1 2H2O 21.076 0.365
TiF 622 1 4e2 T Ti(s) 1 6F2 21.191
Ti21 1 2e2 T Ti(s) 21.60 20.16
Tungsten
W(CN)832 1 e2 T W(CN)842 0.457
W61 1 e2 T W51 0.26 12 F HCl
WO3(s) 1 6H1 1 6e2 T W(s) 1 3H2O 20.091 20.389
n is related to stepwise formation constants (Ki) by n = K1K2 . . . Kn (Box 6-2). nm is the cumulative formation constant for the
reaction mM 1 nL Δ MmLn: nm 5 [MmLn]/([M]m[L]n). The subscript n refers to the ligand and m refers to the metal. Data from
L. G. Sillén and A. E. Martell, Stability Constants of Metal-Ion Complexes (London: The Chemical Society. Special Publications
No. 17 and 25, 1964 and 1971); and A. E. Martell, R. M. Smith, and R. J. Motekaitis, NIST Critical Stability Constants of Metal
Complexes Database 46 (Gaithersburg, MD: National Institute of Standards and Technology, 2001).
(Continued)
1,10-Phenanthroline,
N N
Ag1 5.02 12.07 25 0.1
Ca21 0.7 20 0.1
Cd21 5.17 10.00 14.25 25 0.1
Co21 7.02 13.72 20.10 25 0.1
Cu21 8.82 15.39 20.41 25 0.1
Fe21 5.86 11.11 21.14 25 0.1
Fe31 14.10 25 0.1
Hg21 19.65 23.4 20 0.1
Mn21 4.50 8.65 12.70 25 0.1
Ni21 8.0 16.0 23.9 25 0.1
Zn21 6.30 11.95 17.05 25 0.1