Formic acid

• Formula: CH₂O₂
• Molecular weight: 46.0254
• IUPAC Standard InChI: InChI=1S/CH2O2/c2-1-3/h1H,(H,2,3) Copy

  
• IUPAC Standard InChIKey: BDAGIHXWWSANSR-UHFFFAOYSA-N Copy
• CAS Registry Number: 64-18-6
• Chemical structure:
  This structure is also available as a 2d Mol file or as a computed 3d SD file
  The 3d structure may be viewed using Java or Javascript.
• Other names: Methanoic acid; Aminic acid; Bilorin; Collo-Bueglatt; Collo-Didax; Formisoton; Formylic acid; Hydrogen carboxylic acid; Myrmicyl; HCOOH; Acide formique; Acido formico; Ameisensaeure; Kwas metaniowy; Kyselina mravenci; Mierenzuur; Rcra waste number U123; UN 1779; Formira; Add-F; Amasil
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Reaction thermochemistry data
  • References
  • Notes
• Other data available:
  • Phase change data
  • Henry's Law data
  • Gas phase ion energetics data
  • Ion clustering data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • Vibrational and/or electronic energy levels
  • Gas Chromatography
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
• Options:
  • Switch to SI units

Data at NIST subscription sites:

• NIST / TRC Web Thermo Tables, "lite" edition (thermophysical and thermochemical data)
• NIST / TRC Web Thermo Tables, professional edition (thermophysical and thermochemical data)

NIST subscription sites provide data under the NIST Standard Reference Data Program, but require an annual fee to access. The purpose of the fee is to recover costs associated with the development of data collections included in such sites. Your institution may already be a subscriber. Follow the links above to find out more about the data in these sites and their terms of usage.

Gas phase thermochemistry data

Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, 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:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow

Constant pressure heat capacity of gas

Condensed phase thermochemistry data

Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, 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:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing

Constant pressure heat capacity of liquid

Reaction thermochemistry data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, 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

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

 +  = ( • )

By formula: Cl^- + CH₂O₂ = (Cl^- • CH₂O₂)

 +  =

By formula: CHO₂^- + H⁺ = CH₂O₂

 +  = ( • )

By formula: F^- + CH₂O₂ = (F^- • CH₂O₂)

CH₅O⁺ +  = (CH₅O⁺ • )

By formula: CH₅O⁺ + CH₂O₂ = (CH₅O⁺ • CH₂O₂)

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

 +  = ( • )

By formula: I^- + CH₂O₂ = (I^- • CH₂O₂)

( • ) +  = ( • 2)

By formula: (Cl^- • CH₂O₂) + CH₂O₂ = (Cl^- • 2CH₂O₂)

( • 4) +  = ( • 5)

By formula: (Cl^- • 4CH₂O₂) + CH₂O₂ = (Cl^- • 5CH₂O₂)

( • 2) +  = ( • 3)

By formula: (Cl^- • 2CH₂O₂) + CH₂O₂ = (Cl^- • 3CH₂O₂)

 +  = ( • )

By formula: CHO₂^- + CH₂O₂ = (CHO₂^- • CH₂O₂)

( • 4) +  = ( • 5)

By formula: (CHO₂^- • 4CH₂O₂) + CH₂O₂ = (CHO₂^- • 5CH₂O₂)

( • 3) +  = ( • 4)

By formula: (Cl^- • 3CH₂O₂) + CH₂O₂ = (Cl^- • 4CH₂O₂)

( • 3) +  = ( • 4)

By formula: (CHO₂^- • 3CH₂O₂) + CH₂O₂ = (CHO₂^- • 4CH₂O₂)

( • 2) +  = ( • 3)

By formula: (CHO₂^- • 2CH₂O₂) + CH₂O₂ = (CHO₂^- • 3CH₂O₂)

( • ) +  = ( • 2)

By formula: (CHO₂^- • CH₂O₂) + CH₂O₂ = (CHO₂^- • 2CH₂O₂)

CH₆N⁺ +  = (CH₆N⁺ • )

By formula: CH₆N⁺ + CH₂O₂ = (CH₆N⁺ • CH₂O₂)

Bond type: Hydrogen bonds of the type NH+-O between organics

CH₂NO₅^- +  +  = CH₄NO₆^-

By formula: CH₂NO₅^- + H₂O + CH₂O₂ = CH₄NO₆^-

 +  = CH₂BrO₂^-

By formula: Br^- + CH₂O₂ = CH₂BrO₂^-

CH₂IO₂^- + 2 = C₂H₄IO₄^-

By formula: CH₂IO₂^- + 2CH₂O₂ = C₂H₄IO₄^-

 +  = CH₂NO₅^-

By formula: NO₃^- + CH₂O₂ = CH₂NO₅^-

CH₂BrO₂^- + 2 = C₂H₄BrO₄^-

By formula: CH₂BrO₂^- + 2CH₂O₂ = C₂H₄BrO₄^-

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Notes

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

Guthrie, 1974
Guthrie, J.P., Hydration of carboxamides. Evaluation of the free energy change for addition of water to acetamide and formamide derivatives, J. Am. Chem. Soc., 1974, 96, 3608-3615. [all data]

Lebedeva, 1964
Lebedeva, N.D., Heats of combustion of monocarboxylic acids, Russ. J. Phys. Chem. (Engl. Transl.), 1964, 38, 1435-1437. [all data]

Konicek and Wadso, 1970
Konicek, J.; Wadso, I., Enthalpies of vaporization of organic compounds. VII. Some carboxylic acids, Acta Chem. Scand., 1970, 24, 2612-26. [all data]

Sinke, 1959
Sinke, G.C., The heat of formation of formic acid, J. Phys. Chem., 1959, 63, 2063. [all data]

Millikan R.C., 1957
Millikan R.C., Infrared spectra and vibrational assignment of monomeric formic acid, J. Chem. Phys., 1957, 27, 1305-1308. [all data]

Halford J.O., 1942
Halford J.O., Entropy of the monomeric forms of formic acid and acetic acid, J. Chem. Phys., 1942, 10, 582-584. [all data]

Waring W., 1952
Waring W., Some thermodynamic properties of formic acid, Chem. Rev., 1952, 51, 171-183. [all data]

Chao J., 1986
Chao J., Thermodynamic properties of key organic oxygen compounds in the carbon range C1 to C4. Part 2. Ideal gas properties, J. Phys. Chem. Ref. Data, 1986, 15, 1369-1436. [all data]

Fukushima K., 1971
Fukushima K., Normal coordinate treatment and thermodynamic properties of the cis-trans isomers of formic acid and its deutero-analog, J. Chem. Thermodyn., 1971, 3, 553-562. [all data]

East A.L.L., 1997
East A.L.L., Ab initio statistical thermodynamical models for the computation of third-law entropies, J. Chem. Phys., 1997, 106, 6655-6674. [all data]

Green J.H.S., 1961
Green J.H.S., Thermodynamic properties of organic oxygen compounds. Part III. Formic acid, J. Chem. Soc., 1961, 2241-2242. [all data]

Gurvich, Veyts, et al., 1989
Gurvich, L.V.; Veyts, I.V.; Alcock, C.B., Thermodynamic Properties of Individual Substances, 4th ed.; Vols. 1 and 2, Hemisphere, New York, 1989. [all data]

Chao J., 1978
Chao J., Ideal gas thermodynamic properties of methanoic and ethanoic acids, J. Phys. Chem. Ref. Data, 1978, 7, 363-377. [all data]

Stout and Fisher, 1941
Stout, J.W.; Fisher, L.H., The entropy of formic acid. The heat capacity from 15 to 300K. Heats of fusion and vaporization, J. Chem. Phys., 1941, 9, 163-168. [all data]

Parks, Kelley, et al., 1929
Parks, G.S.; Kelley, K.K.; Huffman, H.M., Thermal data on organic compounds. V. A revision of the entropies and free energies of nineteen organic compounds, J. Am. Chem. Soc., 1929, 51, 1969-1973. [all data]

Gibson, Latimer, et al., 1920
Gibson, G.E.; Latimer, W.M.; Parks, G.S., Entropy changes at low temperatures. I. Formic acid and urea. A test of the third law of thermodynamics, J. Am. Chem. Soc., 1920, 42, 1533-1542. [all data]

Glagoleva and Chervov, 1936
Glagoleva, A.A.; Chervov, S.I., Investigation of the heat capacity of formic acid and its aqueous solutions, Zhur. Obshch. Khim., 1936, 6, 685-690. [all data]

Radulescu and Jula, 1934
Radulescu, D.; Jula, O., Beiträge zur Bestimmung der Abstufung der Polarität des Aminstickstoffes in den organischen Verbindungen, Z. Phys. Chem., 1934, B26, 390-393. [all data]

von Reis, 1881
von Reis, M.A., Die specifische Wärme flüssiger organischer Verbindungen und ihre Beziehung zu deren Moleculargewicht, Ann. Physik [3], 1881, 13, 447-464. [all data]

French, Ikuta, et al., 1982
French, M.A.; Ikuta, S.; Kebarle, P., Hydrogen bonding of O-H and C-H hydrogen donors to Cl^-. Results from mass spectrometric measurement of the ion-molecule equilibria RH + Cl^- = RHCl^-, Can. J. Chem., 1982, 60, 1907. [all data]

Walker and Sunderlin, 1999
Walker, B.W.; Sunderlin, L.S., The thermochemistry of formic acid halide anion clusters, Int. J. Mass Spectrom., 1999, 184, 2-3, 183-189, https://doi.org/10.1016/S1387-3806(99)00008-1 . [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]

Yamdagni and Kebarle, 1971
Yamdagni, R.; Kebarle, P., Hydrogen bonding energies to negative ions from gas phase measurements of ionic equilibria, J. Am. Chem. Soc., 1971, 93, 7139. [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]

Kim, Bradforth, et al., 1995
Kim, E.H.; Bradforth, S.E.; Arnold, D.W.; Metz, R.B.; Neumark, D.M., Study of HCO2 and DCO2 by Negative Ion Photoelectron Spectroscopy, J. Chem. Phys., 1995, 103, 18, 7801, https://doi.org/10.1063/1.470196 . [all data]

Caldwell, Renneboog, et al., 1989
Caldwell, G.; Renneboog, R.; Kebarle, P., Gas Phase Acidities of Aliphatic Carboxylic Acids, Based on Measurements of Proton Transfer Equilibria, Can. J. Chem., 1989, 67, 4, 661, https://doi.org/10.1139/v89-092 . [all data]

Fujio, McIver, et al., 1981
Fujio, M.; McIver, R.T., Jr.; Taft, R.W., Effects on the acidities of phenols from specific substituent-solvent interactions. Inherent substituent parameters from gas phase acidities, J. Am. Chem. Soc., 1981, 103, 4017. [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]

Muftakhov, Vasil'ev, et al., 1999
Muftakhov, M.V.; Vasil'ev, Y.V.; Mazunov, V.A., Determination of electron affinity of carbonyl radicals by means of negative ion mass spectrometry, Rapid Commun. Mass Spectrom., 1999, 13, 12, 1104-1108, https://doi.org/10.1002/(SICI)1097-0231(19990630)13:12<1104::AID-RCM619>3.0.CO;2-C . [all data]

Larson and McMahon, 1983
Larson, J.W.; McMahon, T.B., Strong hydrogen bonding in gas-phase anions. An ion cyclotron resonance determination of fluoride binding energetics to bronsted acids from gas-phase fluoride exchange equilibria measurements, J. Am. Chem. Soc., 1983, 105, 2944. [all data]

Wenthold and Squires, 1995
Wenthold, P.G.; Squires, R.R., Bond dissociation energies of F2(-) and HF2(-). A gas-phase experimental and G2 theoretical study, J. Phys. Chem., 1995, 99, 7, 2002, https://doi.org/10.1021/j100007a034 . [all data]

Arshadi, Yamdagni, et al., 1970
Arshadi, M.; Yamdagni, R.; Kebarle, P., Hydration of Halide Negative Ions in the Gas Phase. II. Comparison of Hydration Energies for the Alkali Positive and Halide Negative Ions, J. Phys. Chem., 1970, 74, 7, 1475, https://doi.org/10.1021/j100702a014 . [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]

Caldwell and Kebarle, 1984
Caldwell, G.; Kebarle, P., Binding energies and structural effects in halide anion-ROH and -RCOOH complexes from gas phase equilibria measurements, J. Am. Chem. Soc., 1984, 106, 967. [all data]

Luczynski, Wlodek, et al., 1978
Luczynski, Z.; Wlodek, S.; Wincel, H., Stabilities of HCOO-.(HCOOH)n and Cl-.(HCOOH)n clusters, Int. J. Mass Spectrom. Ion Phys., 1978, 26, 103. [all data]

Williamson, Knighton, et al., 1996
Williamson, D.H.; Knighton, W.B.; Grimsrud, E.P., Pulsed High Pressure Mass Spectrometry with Near-Viscous Flow Ion Sampling, Int. J. Mass Spectrom. Ion Proc., 1996, 154, 1-2, 15, https://doi.org/10.1016/0168-1176(96)04372-8 . [all data]

Meot-Ner and Sieck, 1986
Meot-Ner, M.; Sieck, L.W., The ionic hydrogen bond and ion solvation. 5. OH...O^- bonds. Gas phase solvation and clustering of alkoxide and carboxylate anions, J. Am. Chem. Soc., 1986, 108, 7525. [all data]

Meot-Ner, 1984
Meot-Ner, (Mautner)M., The Ionic Hydrogen Bond and Ion Solvation. 1. -NH+ O-, -NH+ N- and -OH+ O- Bonds. Correlations with Proton Affinity. Deviations Due to Structural Effects, J. Am. Chem. Soc., 1984, 106, 5, 1257, https://doi.org/10.1021/ja00317a015 . [all data]

Viidanoja, Reiner, et al., 2000
Viidanoja, J.; Reiner, T.; Kiendler, A.; Grimm, F.; Arnold, F., Laboratory investigations of negative ion molecule reactions of propionic, butyric, glyoxylic, pyruvic, and pinonic acids, Int. J. Mass Spectrom., 2000, 194, 1, 53-68, https://doi.org/10.1016/S1387-3806(99)00172-4 . [all data]

Viidanoja, Reiner, et al., 1998
Viidanoja, J.; Reiner, T.; Arnold, F., Laboratory Investigations of Negative Ion-Molecule Reactions of Formic and Acetic Acid., Int. J. Mass Spectrom., 1998, 181, 1-3, 31, https://doi.org/10.1016/S1387-3806(98)14151-9 . [all data]

Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, References

• Symbols used in this document:
  

  Cp,gas	Constant pressure heat capacity of gas
  Cp,liquid	Constant pressure heat capacity of liquid
  S°gas	Entropy of gas at standard conditions
  S°liquid	Entropy of liquid at standard conditions
  ΔcH°liquid	Enthalpy of combustion of liquid at standard conditions
  ΔfH°gas	Enthalpy of formation of gas at standard conditions
  ΔfH°liquid	Enthalpy of formation of liquid at standard conditions
  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
• The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment. However, NIST makes no warranties to that effect, and NIST shall not be liable for any damage that may result from errors or omissions in the Database.
• Customer support for NIST Standard Reference Data products.