Acetaldehyde - The NIST WebBook

Acetaldehyde
  • Formula: C2H4O
  • Molecular weight: 44.0526
  • IUPAC Standard InChI: InChI=1S/C2H4O/c1-2-3/h2H,1H3 Copy InChI version 1.06
  • IUPAC Standard InChIKey: IKHGUXGNUITLKF-UHFFFAOYSA-N Copy
  • CAS Registry Number: 75-07-0
  • Chemical structure: C2H4O This structure is also available as a 2d Mol file or as a computed 3d SD file View 3d structure (requires JavaScript / HTML 5)
  • Other names: Acetic aldehyde; Ethanal; Ethyl aldehyde; CH3CHO; Acetaldehyd; Aldehyde acetique; Aldeide acetica; NCI-C56326; Octowy aldehyd; Acetylaldehyde; Rcra waste number U001; UN 1089; NSC 7594
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  • Information on this page:
    • Reaction thermochemistry data
    • References
    • Notes
  • Other data available:
    • Gas phase thermochemistry data
    • Condensed phase thermochemistry data
    • Phase change data
    • Henry's Law data
    • Gas phase ion energetics data
    • Ion clustering data
    • IR Spectrum
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    • Vibrational and/or electronic energy levels
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Reaction thermochemistry data

Go To: Top, References, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled as indicated in comments: B - John E. Bartmess M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein RCD - Robert C. Dunbar

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. A general reaction search form is also available. Future versions of this site may rely on reaction search pages in place of the enumerated reaction displays seen below.

Individual Reactions

C2H3O- + Hydrogen cation = Acetaldehyde

By formula: C2H3O- + H+ = C2H4O

Quantity Value Units Method Reference Comment
ΔrH°1533.1 ± 3.4kJ/molD-EAMead, Lykke, et al., 1984gas phase; Uncertainty: 6 millical/mol (0.26 micro-eV).Dipolebound state at ca. 14.3 cal/mol (5 cm-1); B
ΔrH°1531. ± 9.2kJ/molG+TSBartmess, Scott, et al., 1979gas phase; Acid: ethanal. The enol is 9.6 kcal/mol more acidic: Holmes and Lossing, 1982; value altered from reference due to change in acidity scale; B
ΔrH°1533. ± 12.kJ/molG+TSCumming and Kebarle, 1978gas phase; B
Quantity Value Units Method Reference Comment
ΔrG°1505. ± 5.0kJ/molH-TSMead, Lykke, et al., 1984gas phase; Uncertainty: 6 millical/mol (0.26 micro-eV).Dipolebound state at ca. 14.3 cal/mol (5 cm-1); B
ΔrG°1502. ± 8.4kJ/molIMREBartmess, Scott, et al., 1979gas phase; Acid: ethanal. The enol is 9.6 kcal/mol more acidic: Holmes and Lossing, 1982; value altered from reference due to change in acidity scale; B
ΔrG°1505. ± 8.4kJ/molIMRECumming and Kebarle, 1978gas phase; B

C2H5O+ + Acetaldehyde = (C2H5O+Acetaldehyde)

By formula: C2H5O+ + C2H4O = (C2H5O+C2H4O)

Bond type: Hydrogen bonds of the type OH-O between organics

Quantity Value Units Method Reference Comment
ΔrH°121.kJ/molICRLarson and McMahon, 1982gas phase; switching reaction((CH3)2OH+)(CH3)2O, Entropy change calculated or estimated; Grimsrud and Kebarle, 1973, Lias, Liebman, et al., 1984, Keesee and Castleman, 1986; M
Quantity Value Units Method Reference Comment
ΔrS°110.J/mol*KN/ALarson and McMahon, 1982gas phase; switching reaction((CH3)2OH+)(CH3)2O, Entropy change calculated or estimated; Grimsrud and Kebarle, 1973, Lias, Liebman, et al., 1984, Keesee and Castleman, 1986; M
Quantity Value Units Method Reference Comment
ΔrG°88.7kJ/molICRLarson and McMahon, 1982gas phase; switching reaction((CH3)2OH+)(CH3)2O, Entropy change calculated or estimated; Grimsrud and Kebarle, 1973, Lias, Liebman, et al., 1984, Keesee and Castleman, 1986; M

C2H7O+ + Acetaldehyde = (C2H7O+Acetaldehyde)

By formula: C2H7O+ + C2H4O = (C2H7O+C2H4O)

Bond type: Hydrogen bonds of the type OH-O between organics

Quantity Value Units Method Reference Comment
ΔrH°131.kJ/molICRLarson and McMahon, 1982gas phase; switching reaction((CH3)2OH+)(CH3)2O, Entropy change calculated or estimated; Grimsrud and Kebarle, 1973, Lias, Liebman, et al., 1984, Keesee and Castleman, 1986; M
Quantity Value Units Method Reference Comment
ΔrS°113.J/mol*KN/ALarson and McMahon, 1982gas phase; switching reaction((CH3)2OH+)(CH3)2O, Entropy change calculated or estimated; Grimsrud and Kebarle, 1973, Lias, Liebman, et al., 1984, Keesee and Castleman, 1986; M
Quantity Value Units Method Reference Comment
ΔrG°97.1kJ/molICRLarson and McMahon, 1982gas phase; switching reaction((CH3)2OH+)(CH3)2O, Entropy change calculated or estimated; Grimsrud and Kebarle, 1973, Lias, Liebman, et al., 1984, Keesee and Castleman, 1986; M

C2H5O+ + Acetaldehyde = (C2H5O+Acetaldehyde)

By formula: C2H5O+ + C2H4O = (C2H5O+C2H4O)

Bond type: Hydrogen bonds of the type OH-O between organics

Quantity Value Units Method Reference Comment
ΔrH°133.kJ/molICRLarson and McMahon, 1982gas phase; switching reaction((CH3)2OH+)(CH3)2O, Entropy change calculated or estimated; Grimsrud and Kebarle, 1973, Lias, Liebman, et al., 1984; M
Quantity Value Units Method Reference Comment
ΔrS°121.J/mol*KN/ALarson and McMahon, 1982gas phase; switching reaction((CH3)2OH+)(CH3)2O, Entropy change calculated or estimated; Grimsrud and Kebarle, 1973, Lias, Liebman, et al., 1984; M
Quantity Value Units Method Reference Comment
ΔrG°97.5kJ/molICRLarson and McMahon, 1982gas phase; switching reaction((CH3)2OH+)(CH3)2O, Entropy change calculated or estimated; Grimsrud and Kebarle, 1973, Lias, Liebman, et al., 1984; M

C2H3O- + Hydrogen cation = Acetaldehyde

By formula: C2H3O- + H+ = C2H4O

Quantity Value Units Method Reference Comment
ΔrH°1645.1 ± 4.0kJ/molD-EANimlos, Soderquist, et al., 1989gas phase; B
ΔrH°1636. ± 8.8kJ/molG+TSDePuy, Bierbaum, et al., 1985gas phase; B
ΔrH°1619. ± 33.kJ/molCIDTGraul and Squires, 1990gas phase; B
ΔrH°<1598.3kJ/molCIDTGraul and Squires, 1988gas phase; B
Quantity Value Units Method Reference Comment
ΔrG°1613. ± 4.6kJ/molH-TSNimlos, Soderquist, et al., 1989gas phase; B
ΔrG°1604. ± 8.4kJ/molIMRBDePuy, Bierbaum, et al., 1985gas phase; B
ΔrG°<1565.9 ± 2.5kJ/molH-TSGraul and Squires, 1988gas phase; B

Chlorine anion + Acetaldehyde = (Chlorine anionAcetaldehyde)

By formula: Cl- + C2H4O = (Cl-C2H4O)

Quantity Value Units Method Reference Comment
ΔrH°60.2 ± 8.4kJ/molIMRELarson and McMahon, 1984gas phase; B,M
Quantity Value Units Method Reference Comment
ΔrS°90.8J/mol*KN/ALarson and McMahon, 1984gas phase; switching reaction(Cl-)t-C4H9F, Entropy change calculated or estimated; Larson and McMahon, 1984, 2; M
Quantity Value Units Method Reference Comment
ΔrG°33. ± 8.4kJ/molIMRELarson and McMahon, 1984gas phase; B,M

MeCO2 anion + Acetaldehyde = (MeCO2 anionAcetaldehyde)

By formula: C2H3O2- + C2H4O = (C2H3O2-C2H4O)

Bond type: Hydrogen bonds of deprotonated acids to ketones/

Quantity Value Units Method Reference Comment
ΔrH°68.2 ± 4.2kJ/molTDAsMeot-ner, 1988gas phase; B,M
Quantity Value Units Method Reference Comment
ΔrS°90.8J/mol*KPHPMSMeot-ner, 1988gas phase; M
Quantity Value Units Method Reference Comment
ΔrG°41. ± 8.4kJ/molTDAsMeot-ner, 1988gas phase; B

Hydrogen + Acetaldehyde = Ethanol

By formula: H2 + C2H4O = C2H6O

Quantity Value Units Method Reference Comment
ΔrH°-81.3 ± 1.4kJ/molChydWiberg, Crocker, et al., 1991liquid phase; solvent: Triglyme; ALS
ΔrH°-69.08 ± 0.42kJ/molChydDolliver, Gresham, et al., 1938gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -70.1 ± 0.4 kJ/mol; At 355 °K; ALS

(C2H5O-4294967295Acetaldehyde) + Acetaldehyde = C2H5O-

By formula: (C2H5O-4294967295C2H4O) + C2H4O = C2H5O-

Quantity Value Units Method Reference Comment
ΔrH°158. ± 4.2kJ/molN/ARamond, Davico, et al., 2000gas phase; B
ΔrH°165. ± 9.2kJ/molTherBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B

Nitric oxide anion + Acetaldehyde = (Nitric oxide anionAcetaldehyde)

By formula: NO- + C2H4O = (NO-C2H4O)

Quantity Value Units Method Reference Comment
ΔrH°164.kJ/molICRReents and Freiser, 1981gas phase; switching reaction,Thermochemical ladder(NO+)C2H5OH, Entropy change calculated or estimated; Farid and McMahon, 1978; M

Lithium ion (1+) + Acetaldehyde = (Lithium ion (1+)Acetaldehyde)

By formula: Li+ + C2H4O = (Li+C2H4O)

Quantity Value Units Method Reference Comment
ΔrH°173.kJ/molICRStaley and Beauchamp, 1975gas phase; switching reaction(Li+)H2O, Keesee and Castleman, 1986 from Berman and Beauchamp, 1986; Dzidic and Kebarle, 1970 interpolated; M

3Acetaldehyde = Paraldehyde

By formula: 3C2H4O = C6H12O3

Quantity Value Units Method Reference Comment
ΔrH°-87. ± 6.kJ/molCmKrasnov, Ozherel'eva, et al., 1983liquid phase; solvent: Nonaqueous; Trimerization; ALS
ΔrH°-98.1kJ/molEqkBusfield, Lee, et al., 1973gas phase; ALS

Magnesium ion (1+) + Acetaldehyde = (Magnesium ion (1+)Acetaldehyde)

By formula: Mg+ + C2H4O = (Mg+C2H4O)

Quantity Value Units Method Reference Comment
ΔrH°260. ± 20.kJ/molICROperti, Tews, et al., 1988gas phase; switching reaction,Thermochemical ladder(Mg+)CH3OH; M

Ethane, 1,1-dimethoxy- + Water = 2Methyl Alcohol + Acetaldehyde

By formula: C4H10O2 + H2O = 2CH4O + C2H4O

Quantity Value Units Method Reference Comment
ΔrH°36.07 ± 0.063kJ/molCmWiberg, 1980liquid phase; solvent: Water; Hydrolysis; ALS

1,1-Dimethoxyethane + Water = 2Methyl Alcohol + Acetaldehyde

By formula: C4H10O2 + H2O = 2CH4O + C2H4O

Quantity Value Units Method Reference Comment
ΔrH°35.7 ± 0.3kJ/molCmBirley and Skinner, 1970liquid phase; Heat of hydrolysis; ALS

Ethane, 1,2-dimethoxy- + Water = 2Methyl Alcohol + Acetaldehyde

By formula: C4H10O2 + H2O = 2CH4O + C2H4O

Quantity Value Units Method Reference Comment
ΔrH°35.9 ± 0.8kJ/molEqkWiberg, Morgan, et al., 1994liquid phase; ALS

2Methyl Alcohol + Acetaldehyde = Ethane, 1,2-dimethoxy- + Water

By formula: 2CH4O + C2H4O = C4H10O2 + H2O

Quantity Value Units Method Reference Comment
ΔrH°-62. ± 1.kJ/molCmWiberg, Morgan, et al., 1994gas phase; ALS

Acetaldehyde + Iodine = Hydrogen iodide + Acetyl iodide

By formula: C2H4O + I2 = HI + C2H3IO

Quantity Value Units Method Reference Comment
ΔrH°3. ± 2.kJ/molEqkWalsh and Benson, 1966gas phase; ALS

Water + Acetaldehyde, phenylhydrazone = Hydrazine, phenyl- + Acetaldehyde

By formula: H2O + C8H10N2 = C6H8N2 + C2H4O

Quantity Value Units Method Reference Comment
ΔrH°-61.1kJ/molCmLandrieu, 1905solid phase; ALS

Paraldehyde = 3Acetaldehyde

By formula: C6H12O3 = 3C2H4O

Quantity Value Units Method Reference Comment
ΔrH°98.1kJ/molEqkBusfield, Lee, et al., 1973gas phase; At 292-313 K; ALS

Sodium ion (1+) + Acetaldehyde = (Sodium ion (1+)Acetaldehyde)

By formula: Na+ + C2H4O = (Na+C2H4O)

Quantity Value Units Method Reference Comment
ΔrH°113. ± 3.kJ/molCIDTArmentrout and Rodgers, 2000RCD

Silver ion (1+) + Acetaldehyde = (Silver ion (1+)Acetaldehyde)

By formula: Ag+ + C2H4O = (Ag+C2H4O)

Quantity Value Units Method Reference Comment
ΔrH°182. ± 19.kJ/molRAKHo, Yang, et al., 1997RCD

References

Go To: Top, Reaction thermochemistry data, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Mead, Lykke, et al., 1984 Mead, R.D.; Lykke, K.R.; Lineberger, W.C.; Marks, J.; Brauman, J.I., Spectroscopy and Dynamics of the Dipole-Bound State of Acetaldehyde Enolate., J. Chem. Phys., 1984, 81, 11, 4883., https://doi.org/10.1063/1.447515 . [all data]

Bartmess, Scott, et al., 1979 Bartmess, J.E.; Scott, J.A.; McIver, R.T., Jr., The gas phase acidity scale from methanol to phenol, J. Am. Chem. Soc., 1979, 101, 6047. [all data]

Holmes and Lossing, 1982 Holmes, J.L.; Lossing, F.P., Heats of formation of the ionic and neutral enols of acetaldehyde and acetone, J. Am. Chem. Soc., 1982, 104, 2648. [all data]

Cumming and Kebarle, 1978 Cumming, J.B.; Kebarle, P., Summary of gas phase measurements involving acids AH. Entropy changes in proton transfer reactions involving negative ions. Bond dissociation energies D(A-H) and electron affinities EA(A), Can. J. Chem., 1978, 56, 1. [all data]

Larson and McMahon, 1982 Larson, J.W.; McMahon, T.B., Formation, Thermochemistry, and Relative Stabilities of Proton - Bound dimers of Oxygen n - Donor Bases from Ion Cyclotron Resonance Solvent - Exchange Equilibria Measurements, J. Am. Chem. Soc., 1982, 104, 23, 6255, https://doi.org/10.1021/ja00387a016 . [all data]

Grimsrud and Kebarle, 1973 Grimsrud, E.P.; Kebarle, P., Gas Phase Ion Equilibria Studies of the Solvation of the Hydrogen Ion by Methanol, Dimethyl Ether and Water. Effect of Hydrogen Bonding, J. Am. Chem. Soc., 1973, 95, 24, 7939, https://doi.org/10.1021/ja00805a002 . [all data]

Lias, Liebman, et al., 1984 Lias, S.G.; Liebman, J.F.; Levin, R.D., Evaluated gas phase basicities and proton affinities of molecules heats of formation of protonated molecules, J. Phys. Chem. Ref. Data, 1984, 13, 695. [all data]

Keesee and Castleman, 1986 Keesee, R.G.; Castleman, A.W., Jr., Thermochemical data on Ggs-phase ion-molecule association and clustering reactions, J. Phys. Chem. Ref. Data, 1986, 15, 1011. [all data]

Nimlos, Soderquist, et al., 1989 Nimlos, M.R.; Soderquist, J.A.; Ellison, G.B., Spectroscopy of CH3CO- and CH3CO, J. Am. Chem. Soc., 1989, 111, 20, 7675, https://doi.org/10.1021/ja00202a001 . [all data]

DePuy, Bierbaum, et al., 1985 DePuy, C.H.; Bierbaum, V.M.; Damrauer, R.; Soderquist, J.A., Gas-phase reactions of the acetyl anion, J. Am. Chem. Soc., 1985, 107, 3385. [all data]

Graul and Squires, 1990 Graul, S.T.; Squires, R.R., Gas-Phase Acidities Derived from Threshold Energies for Activated Reactions, J. Am. Chem. Soc., 1990, 112, 7, 2517, https://doi.org/10.1021/ja00163a007 . [all data]

Graul and Squires, 1988 Graul, S.T.; Squires, R.R., On the Existence of Alkyl Carbanions in the Gas Phase, J. Am. Chem. Soc., 1988, 110, 2, 607, https://doi.org/10.1021/ja00210a054 . [all data]

Larson and McMahon, 1984 Larson, J.W.; McMahon, T.B., Hydrogen bonding in gas phase anions. An experimental investigation of the interaction between chloride ion and bronsted acids from ICR chloride exchange equilibria, J. Am. Chem. Soc., 1984, 106, 517. [all data]

Larson and McMahon, 1984, 2 Larson, J.W.; McMahon, T.B., Gas phase negative ion chemistry of alkylchloroformates, Can. J. Chem., 1984, 62, 675. [all data]

Meot-ner, 1988 Meot-ner, M., Ionic Hydrogen Bond and Ion Solvation. 6. Interaction Energies of the Acetate Ion with Organic Molecules. Comparison of CH3COO- with Cl-, CN-, and SH-, J. Am. Chem. Soc., 1988, 110, 12, 3854, https://doi.org/10.1021/ja00220a022 . [all data]

Wiberg, Crocker, et al., 1991 Wiberg, K.B.; Crocker, L.S.; Morgan, K.M., Thermochemical studies of carbonyl compounds. 5. Enthalpies of reduction of carbonyl groups, J. Am. Chem. Soc., 1991, 113, 3447-3450. [all data]

Dolliver, Gresham, et al., 1938 Dolliver, M.A.; Gresham, T.L.; Kistiakowsky, G.B.; Smith, E.A.; Vaughan, W.E., Heats of organic reactions. VI. Heats of hydrogenation of some oxygen-containing compounds, J. Am. Chem. Soc., 1938, 60, 440-450. [all data]

Cox and Pilcher, 1970 Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]

Ramond, Davico, et al., 2000 Ramond, T.M.; Davico, G.E.; Schwartz, R.L.; Lineberger, W.C., Vibronic structure of alkoxy radicals via photoelectron spectroscopy, J. Chem. Phys., 2000, 112, 3, 1158-1169, https://doi.org/10.1063/1.480767 . [all data]

Reents and Freiser, 1981 Reents, W.D.; Freiser, B.S., Gas-Phase Binding Energies and Spectroscopic Properties of NO+ Charge-Transfer Complexes, J. Am. Chem. Soc., 1981, 103, 2791. [all data]

Farid and McMahon, 1978 Farid, R.; McMahon, T.B., Gas-Phase Ion-Molecule Reactions of Alkyl Nitrites by Ion Cyclotron Resonance Spectroscopy, Int. J. Mass Spectrom. Ion Phys., 1978, 27, 2, 163, https://doi.org/10.1016/0020-7381(78)80037-0 . [all data]

Staley and Beauchamp, 1975 Staley, R.H.; Beauchamp, J.L., Intrinsic Acid - Base Properties of Molecules. Binding Energies of Li+ to pi - and n - Donor Bases, J. Am. Chem. Soc., 1975, 97, 20, 5920, https://doi.org/10.1021/ja00853a050 . [all data]

Berman and Beauchamp, 1986 Berman, D.W.; Beauchamp, J.L., Quoted in Keesee and Castleman, 1986, 1986. [all data]

Dzidic and Kebarle, 1970 Dzidic, I.; Kebarle, P., Hydration of the Alkali Ions in the Gas Phase. Enthalpies and Entropies of Reactions M+(H2O)n-1 + H2O = M+(H2O)n, J. Phys. Chem., 1970, 74, 7, 1466, https://doi.org/10.1021/j100702a013 . [all data]

Krasnov, Ozherel'eva, et al., 1983 Krasnov, V.L.; Ozherel'eva, N.K.; Trub, E.P.; Tsvetkov, V.G.; Bodrikov, I.V., Trimerization of aldehydes under the action of sulfur dioxide, J. Gen. Chem. USSR, 1983, 53, 2135-2138. [all data]

Busfield, Lee, et al., 1973 Busfield, W.K.; Lee, R.M.; Merifold, D., Gas phase equilibrium between acetaldehyde and paraldehyde, thermodynamic values for the trimerisation of acetaldehyde and the polymerisability of paraldehyde, J. Chem. Soc. Faraday Trans. 1, 1973, 69, 936-940. [all data]

Operti, Tews, et al., 1988 Operti, L.; Tews, E.C.; Freiser, B.S., Determination of Gas-Phase Ligand Binding Energies to Mg+ by FTMS Techniques, J. Am. Chem. Soc., 1988, 110, 12, 3847, https://doi.org/10.1021/ja00220a020 . [all data]

Wiberg, 1980 Wiberg, K.B., Energies of organic compounds, Rept. DOE-E(11-1)4060 Prepared for US Dept. of Energy by Yale Univ., New Haven, CT. Avail. NTIS, 1980, 1-24. [all data]

Birley and Skinner, 1970 Birley, G.I.; Skinner, H.A., Enthalpies of hydrolysis of dimethoxymethane and 1,1-dimethoxyethane, Trans. Faraday Soc., 1970, 66, 791-793. [all data]

Wiberg, Morgan, et al., 1994 Wiberg, K.B.; Morgan, K.M.; Maltz, H., Thermochemistry of carbonyl reactions. 6. A study of hydration equilibria, J. Am. Chem. Soc., 1994, 116, 11067-11077. [all data]

Walsh and Benson, 1966 Walsh, R.; Benson, S.W., The heats of formation of acetyl iodide and the acetyl radical, J. Phys. Chem., 1966, 70, 3751-3753. [all data]

Landrieu, 1905 Landrieu, M.Ph., Thermochimie. - Thermochimie des hydrazones, Compt. Rend., 1905, 141, 358-361. [all data]

Armentrout and Rodgers, 2000 Armentrout, P.B.; Rodgers, M.T., An Absolute Sodium Cation Affinity Scale: Threshold Collision-Induced Dissociation Experiments and ab Initio Theory, J. Phys. Chem A, 2000, 104, 11, 2238, https://doi.org/10.1021/jp991716n . [all data]

Ho, Yang, et al., 1997 Ho, Y.-P.; Yang, Y.-C.; Klippenstein, S.J.; Dunbar, R.C., Binding Energies of Ag+ and Cd+ Complexes from Analysis of Radiative Association Kinetics, J. Phys. Chem. A, 1997, 101, 18, 3338, https://doi.org/10.1021/jp9637284 . [all data]

Notes

Go To: Top, Reaction thermochemistry data, References

  • Symbols used in this document:
    ΔrG° Free energy of reaction at standard conditions
    ΔrH° Enthalpy of reaction at standard conditions
    ΔrS° Entropy of reaction at standard conditions
  • Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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