E5: Acid Dissociation Constants of Organics (2024)

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    The following table provides pKa and Ka values for selected weak acids. All values are from Martell, A. E.; Smith, R. M. Critical Stability Constants, Vols. 1–4. Plenum Press: New York, 1976. Unless otherwise stated, values are for 25 oC and for zero ionic strength. Those values in brackets are considered less reliable.

    Weak acids are arranged alphabetically by the names of the neutral compounds from which they are derived. In some cases—such as acetic acid—the compound is the weak acid. In other cases—such as for the ammonium ion—the neutral compound is the conjugate base. Chemical formulas or structural formulas are shown for the fully protonated weak acid. Successive acid dissociation constants are provided for polyprotic weak acids; where there is ambiguity, the specific acidic proton is identified.

    To find the Kb value for a conjugate weak base, recall that

    \[K_\text{a} \times K_\text{b} = K_\text{w} \nonumber\]

    for a conjugate weak acid, HA, and its conjugate weak base, A.

    compound conjugate acid pKa Ka
    acetic acid \(\ce{CH3COOH}\) 4.757 \(1.75 \times 10^{-5}\)
    adipic acid
    E5: Acid Dissociation Constants of Organics (1)

    4.42

    5.42

    \(3.8 \times 10^{-5}\)

    \(3.8 \times 10^{-6}\)

    alanine E5: Acid Dissociation Constants of Organics (2)

    2.348 (\(\ce{COOH}\))

    9.867 (\(\ce{NH3}\))

    \(4.49 \times 10^{-3}\)

    \(1.36 \times 10^{-10}\)

    aminobenzene E5: Acid Dissociation Constants of Organics (3) 4.601 \(2.51 \times 10^{-5}\)
    4-aminobenzene sulfonic acid E5: Acid Dissociation Constants of Organics (4) 3.232 \(5.86 \times 10^{-4}\)
    2-aminobenzoic acid
    E5: Acid Dissociation Constants of Organics (5)

    2.08 (\(\ce{COOH}\))

    4.96 (\(\ce{NH3}\))

    \(8.3 \times 10^{-3}\)

    \(1.1 \times 10^{-5}\)

    2-aminophenol (\(T = 20 \text{°C}\)) E5: Acid Dissociation Constants of Organics (6)

    4.78 (\(\ce{NH3}\))

    9.97 (OH)

    \(1.7 \times 10^{-5}\)

    \(1.05 \times 10^{-10}\)

    ammonia \(\ce{NH4+}\) 9.244 \(5.70 \times 10^{-10}\)
    arginine
    E5: Acid Dissociation Constants of Organics (7)

    1.823 (COOH)

    8.991 (\(\ce{NH3}\))

    [12.48] (\(\ce{NH2}\))

    \(1.50 \times 10^{-2}\)

    \(1.02 \times 10^{-9}\)

    [\(3.3 \times 10^{-13}\)]

    arsenic acid \(\ce{H3AsO4}\)

    2.24

    6.96

    11.50

    \(5.8 \times 10^{-3}\)

    \(1.1 \times 10^{-7}\)

    \(3.2 \times 10^{-12}\)

    asparagine (\(\mu = 0.1 \text{ M}\)) E5: Acid Dissociation Constants of Organics (8)

    2.14 (COOH)

    8.72 (\(\ce{NH3}\))

    \(7.2 \times 10^{-3}\)

    \(1.9 \times 10^{-9}\)

    aspartic acid E5: Acid Dissociation Constants of Organics (9)

    1.990 (\(\alpha\)-COOH)

    3.900 (\(\beta\)-COOH)

    10.002 (\(\ce{NH3}\))

    \(1.02 \times 10^{-2}\)

    \(1.26 \times 10^{-4}\)

    \(9.95 \times 10^{-11}\)

    benzoic acid E5: Acid Dissociation Constants of Organics (10) 4.202 \(6.28 \times 10^{-5}\)
    benzylamine E5: Acid Dissociation Constants of Organics (11) 9.35 \(4.5 \times 10^{-10}\)
    boric acid (\(pK_\text{a2}, pK_\text{a3: } T = 20 \text{°C}\)) \(\ce{H3BO3}\)

    9.236

    [12.74]

    [13.80]

    \(5.81 \times 10^{-10}\)

    [\(1.82 \times 10^{-13}\)]

    [\(1.58 \times 10^{-14}\)]

    carbonic acid \(\ce{H2CO3}\)

    6.352

    10.329

    \(4.45 \times 10^{-7}\)

    \(4.69 \times 10^{-11}\)

    catechol E5: Acid Dissociation Constants of Organics (12)

    9.40

    12.8

    \(4.0 \times 10^{-10}\)

    \(1.6 \times 10^{-13}\)

    chloracetic acid \(\ce{ClCH2COOH}\) 2.865 \(1.36 \times 10^{-3}\)
    chromic acid (\(pK_\text{a1: } T = 20 \text{°C}\)) \(\ce{H2CrO4}\)

    –0.2

    6.51

    1.6

    \(3.1 \times 10^{-7}\)

    citric acid E5: Acid Dissociation Constants of Organics (13)

    3.128 (COOH)

    4.761 (COOH)

    6.396 (COOH)

    \(7.45 \times 10^{-4}\)

    \(1.73 \times 10^{-5}\)

    \(4.02 \times 10^{-7}\)

    cupferron (\(\mu = 0.1 \text{ M}\)) E5: Acid Dissociation Constants of Organics (14) 4.16 \(6.9 \times 10^{-5}\)
    cysteine E5: Acid Dissociation Constants of Organics (15)

    [1.71] (COOH)

    8.36 (SH)

    10.77 (\(\ce{NH3}\))

    [\(1.9 \times 10^{-2}\)]

    \(4.4 \times 10^{-9}\)

    \(1.7 \times 10^{-11}\)

    dichloracetic acid \(\ce{Cl2CHCOOH}\) 1.30 \(5.0 \times 10^{-2}\)
    diethylamine \(\ce{(CH3CH2)2NH2+}\) 10.933 \(1.17 \times 10^{-11}\)
    dimethylamine \(\ce{(CH3)2NH2+}\) 10.774 \(1.68 \times 10^{-11}\)
    dimethylglyoxime E5: Acid Dissociation Constants of Organics (16)

    10.66

    12.0

    \(2.2 \times 10^{-11}\)

    \(1. \times 10^{-12}\)

    ethylamine \(\ce{CH3CH2NH3+}\) 10.636 \(2.31 \times 10^{-11}\)
    ethylenediamine \(\ce{+H3NCH2CH2NH3+}\)

    6.848

    9.928

    \(1.42 \times 10^{-7}\)

    \(1.18 \times 10^{-10}\)

    ethylenediaminetetracetic acid

    (EDTA) (\(\mu = 0.1 \text{ M}\))

    E5: Acid Dissociation Constants of Organics (17)

    0.0 (COOH)

    1.5 (COOH)

    2.0 (COOH)

    2.66 (COOH)

    6.16 (NH)

    10.24 (NH)

    1.0

    \(3.2 \times 10^{-2}\)

    \(1.0 \times 10^{-2}\)

    \(2.2 \times 10^{-3}\)

    \(6.9 \times 10^{-7}\)

    \(5.8 \times 10^{-11}\)

    formic acid \(\ce{HCOOH}\) 3.745 \(1.80 \times 10^{-4}\)
    fumaric acid E5: Acid Dissociation Constants of Organics (18)

    3.053

    4.494

    \(8.85 \times 10^{-4}\)

    \(3.21 \times 10^{-5}\)

    glutamic acid
    E5: Acid Dissociation Constants of Organics (19)

    2.33 (\(\alpha\)-COOH)

    4.42 (\(\lambda\)-COOH)

    9.95 (\(\ce{NH3}\))

    \(5.9 \times 10^{-3}\)

    \(3.8\times 10^{-5}\)

    \(1.12 \times 10^{-10}\)

    glutamine E5: Acid Dissociation Constants of Organics (20)

    2.17 (COOH)

    9.01 (\(\ce{NH3}\))

    \(6.8 \times 10^{-3}\)

    \(9.8 \times 10^{-10}\)

    glycine E5: Acid Dissociation Constants of Organics (21)

    2.350 (COOH)

    9.778 (\(\ce{NH3}\))

    \(4.47 \times 10^{-3}\)

    \(1.67 \times 10^{-10}\)

    glycolic acid \(\ce{HOOCH2COOH}\)

    3.881 (COOH)

    \(1.48 \times 10^{-4}\)
    histidine (\(\mu = 0.1 \text{ M}\)) E5: Acid Dissociation Constants of Organics (22)

    1.7 (COOH)

    6.02 (NH)

    9.08 (\(\ce{NH3}\))

    \(2. \times 10^{-2}\)

    \(9.5 \times 10^{-7}\)

    \(8.3 \times 10^{-10}\)

    hydrogen cyanide \(\ce{HCN}\) 9.21 \(6.2 \times 10^{-10}\)
    hydrogen fluroride \(\ce{HF}\) 3.17 \(6.8 \times 10^{-4}\)
    hydrogen peroxide \(\ce{H2O2}\) 11.65 \(2.2 \times 10^{-12}\)
    hydrogen sulfide \(\ce{H2S}\)

    7.02

    13.9

    \(9.5 \times 10^{-8}\)

    \(1.3 \times 10^{-14}\)

    hydrogen thiocyanate \(\ce{HSCN}\) 0.9 \(1.3 \times 10^{-1}\)
    8-hydroxyquinoline E5: Acid Dissociation Constants of Organics (23)

    4.9 (NH)

    9.81 (OH)

    \(1.2 \times 10^{-5}\)

    \(1.6 \times 10^{-10}\)

    hydroxylamine \(\ce{HONH3+}\) 5.96 \(1.1 \times 10^{-6}\)
    hypobromous acid \(\ce{HOBr}\) 8.63 \(2.3 \times 10^{-9}\)
    hypochlorous acid \(\ce{HOCl}\) 7.53 \(3.0\times 10^{-8}\)
    hypoiodous acid \(\ce{HOI}\) 10.64 \(2.3 \times 10^{-11}\)
    iodic acid \(\ce{HIO3}\) 0.77 \(1.7 \times 10^{-1}\)
    isoleucine
    E5: Acid Dissociation Constants of Organics (24)

    2.319 (COOH)

    9.754 (\(\ce{NH3}\))

    \(4.8 \times 10^{-3}\)

    \(1.76 \times 10^{-10}\)

    leucine E5: Acid Dissociation Constants of Organics (25)

    2.329 (COOH)

    9.747 (\(\ce{NH3}\))

    \(4.69 \times 10^{-3}\)

    \(1.79 \times 10^{-10}\)

    lysine (\(\mu = 0.1 \text{ M}\)) E5: Acid Dissociation Constants of Organics (26)

    2.04 (COOH)

    9.08 (\(\alpha \text{-} \ce{NH3}\))

    10.69 (\(\epsilon \text{-} \ce{NH3}\))

    \(9.1 \times 10^{-3}\)

    \(8.3 \times 10^{-10}\)

    \(2.0 \times 10^{-11}\)

    maleic acid E5: Acid Dissociation Constants of Organics (27)

    1.910

    6.332

    \(1.23 \times 10^{-2}\)

    \(4.66 \times 10^{-7}\)

    malic acid E5: Acid Dissociation Constants of Organics (28)

    3.459 (COOH)

    5.097 (COOH)

    \(3.48 \times 10^{-4}\)

    \(8.00 \times 10^{-6}\)

    malonic acid \(\ce{HOOCCH2COOH}\)

    2.847

    5.696

    \(1.42 \times 10^{-3}\)

    \(2.01 \times 10^{-6}\)

    methionine (\(\mu = 0.1 \text{ M}\)) E5: Acid Dissociation Constants of Organics (29)

    2.20 (COOH)

    9.05 (\(\ce{NH3}\))

    \(6.3 \times 10^{-3}\)

    \(8.9 \times 10^{-10}\)

    methylamine \(\ce{CH3NH3+}\) 10.64 \(2.3 \times 10^{-11}\)
    2-methylanaline E5: Acid Dissociation Constants of Organics (30) 4.447 \(3.57 \times 10^{-5}\)
    4-methylanaline E5: Acid Dissociation Constants of Organics (31) 5.084 \(8.24 \times 10^{-6}\)
    2-methylphenol E5: Acid Dissociation Constants of Organics (32) 10.28 \(5.2 \times 10^{-11}\)
    4-methylphenol E5: Acid Dissociation Constants of Organics (33) 10.26 \(5.5 \times 10^{-11}\)

    nitrilotriacetic acid

    (\(T = 20 \text{°C}), pK_\text{a1: } \mu = 0.1 \text{ M}\))

    E5: Acid Dissociation Constants of Organics (34)

    1.1 (COOH)

    1.650 (COOH)

    2.940 (COOH)

    10.334 (\(\ce{NH3}\))

    \(8. \times 10^{-2}\)

    \(2.24 \times 10^{-2}\)

    \(1.15 \times 10^{-3}\)

    \(4.63 \times 10^{-11}\)

    2-nitrobenzoic acid E5: Acid Dissociation Constants of Organics (35) 2.179 \(6.62 \times 10^{-3}\)
    3-nitrobenzoic acid E5: Acid Dissociation Constants of Organics (36) 3.449 \(3.56 \times 10^{-4}\)
    4-nitrobenzoic acid E5: Acid Dissociation Constants of Organics (37) 3.442 \(3.61 \times 10^{-4}\)
    2-nitrophenol E5: Acid Dissociation Constants of Organics (38) 7.21 \(6.2 \times 10^{-8}\)
    3-nitrophenol
    E5: Acid Dissociation Constants of Organics (39)
    8.39 \(4.1 \times 10^{-9}\)
    4-nitrophenol E5: Acid Dissociation Constants of Organics (40) 7.15 \(7.1 \times 10^{-8}\)
    nitrous acid \(\ce{HNO2}\) 3.15 \(7.1 \times 10^{-4}\)
    oxalic acid \(\ce{H2C2O4}\)

    1.252

    4.266

    \(5.60 \times 10^{-2}\)

    \(5.42 \times 10^{-5}\)

    1,10-phenanthroline E5: Acid Dissociation Constants of Organics (41) 4.86 \(1.38 \times 10^{-5}\)
    phenol E5: Acid Dissociation Constants of Organics (42) 9.98 \(1.05 \times 10^{-10}\)
    phenylalanine E5: Acid Dissociation Constants of Organics (43)

    2.20 (COOH)

    9.31 (\(\ce{NH3}\))

    \(6.3 \times 10^{-3}\)

    \(4.9 \times 10^{-10}\)

    phosphoric acid \(\ce{H3PO4}\)

    2.148

    7.199

    12.35

    \(7.11 \times 10^{-3}\)

    \(6.32 \times 10^{-8}\)

    \(4.5 \times 10^{-13}\)

    phthalic acid E5: Acid Dissociation Constants of Organics (44)

    2.950

    5.408

    \(1.12 \times 10^{-3}\)

    \(3.91 \times 10^{-6}\)

    piperdine E5: Acid Dissociation Constants of Organics (45) 11.123 \(7.53 \times 10^{-12}\)
    proline E5: Acid Dissociation Constants of Organics (46)

    1.952 (COOH)

    10.650 (NH)

    \(1.12 \times 10^{-2}\)

    \(2.29 \times 10^{-11}\)

    propanoic acid \(\ce{CH3CH2COOH}\)

    4.874

    \(1.34 \times 10^{-5}\)
    propylamine \(\ce{CH3CH2CH2NH3+}\) 10.566 \(2.72 \times 10^{-11}\)
    pyridine E5: Acid Dissociation Constants of Organics (47) 5.229 \(5.90 \times 10^{-6}\)
    resorcinol E5: Acid Dissociation Constants of Organics (48)

    9.30

    11.06

    \(5.0 \times 10^{-10}\)

    \(8.7 \times 10^{-12}\)

    salicylic acid E5: Acid Dissociation Constants of Organics (49)

    2.97 (COOH)

    13.74 (OH)

    \(1.1 \times 10^{-3}\)

    \(1.8 \times 10^{-14}\)

    serine E5: Acid Dissociation Constants of Organics (50)

    2.187 (COOH)

    9.209 (\(\ce{NH3}\))

    \(6.50 \times 10^{-3}\)

    \(6.18 \times 10^{-10}\)

    succinic acid E5: Acid Dissociation Constants of Organics (51)

    4.207

    5.636

    \(6.21 \times 10^{-5}\)

    \(2.31 \times 10^{-6}\)

    sulfuric acid \(\ce{H2SO4}\)

    strong

    1.99

    \(1.0 \times 10^{-2}\)

    sulfurous acid \(\ce{H2SO3}\)

    1.91

    7.18

    \(1.2 \times 10^{-2}\)

    \(6.6 \times 10^{-8}\)

    D-tartaric acid E5: Acid Dissociation Constants of Organics (52)

    3.036 (COOH)

    4.366 (COOH)

    \(9.20 \times 10^{-4}\)

    \(4.31 \times 10^{-5}\)

    threonine E5: Acid Dissociation Constants of Organics (53)

    2.088 (COOH)

    9.100 (\(\ce{NH3}\))

    \(8.17 \times 10^{-3}\)

    \(7.94 \times 10^{-10}\)

    thiosulfuric acid \(\ce{H2S2O3}\)

    0.6

    1.6

    \(3. \times 10^{-1}\)

    \(3. \times 10^{-2}\)

    trichloracetic acid (\(\mu = 0.1 \text{ M}\)) \(\ce{Cl3CCOOH}\) 0.66 \(2.2 \times 10^{-1}\)
    triethanolamine \(\ce{(HOCH2CH2)3NH+}\) 7.762 \(1.73 \times 10^{-8}\)
    triethylamine \(\ce{(CH3CH2)3NH+}\) 10.715 \(1.93 \times 10^{-11}\)
    trimethylamine \(\ce{(CH3)3NH+}\) 9.800 \(1.58 \times 10^{-10}\)
    tris(hydroxymethyl)amino methane (TRIS or THAM) \(\ce{(HOCH2)3CNH3+}\) 8.075 \(8.41 \times 10^{-9}\)
    tryptophan (\(\mu = 0.1 \text{ M}\))
    E5: Acid Dissociation Constants of Organics (54)

    2.35 (COOH)

    9.33 (\(\ce{NH3}\))

    \(4.5 \times 10^{-3}\)

    \(4.7 \times 10^{-10}\)

    tyrosine (\(pK_\text{a1: } \mu = 0.1 \text{ M}\)) E5: Acid Dissociation Constants of Organics (55)

    2.17 (COOH)

    9.19 (\(\ce{NH3}\))

    10.47 (OH)

    \(6.8 \times 10^{-3}\)

    \(6.5 \times 10^{-10}\)

    \(3.4 \times 10^{-11}\)

    valine E5: Acid Dissociation Constants of Organics (56)

    2.286 (COOH)

    9.718 (\(\ce{NH3}\))

    \(5.18 \times 10^{-3}\)

    \(1.91 \times 10^{-10}\)

    E5: Acid Dissociation Constants of Organics (2024)

    References

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