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
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• Information on this page:
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • Henry's Law data
  • Ion clustering data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • Vibrational and/or electronic energy levels
  • Gas Chromatography
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  • Gas Phase Kinetics Database
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Reaction thermochemistry data

Go To: Top, Gas phase ion energetics 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^-

Gas phase ion energetics data

Go To: Top, 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 evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias
L - Sharon G. Lias

Data compiled as indicated in comments:
B - John E. Bartmess
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
LL - Sharon G. Lias and Joel F. Liebman

Ionization energy determinations

Appearance energy determinations

De-protonation reactions

 +  =

By formula: CHO₂^- + H⁺ = CH₂O₂

References

Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, Notes

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

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]

Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G., Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update, J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018 . [all data]

Traeger, 1985
Traeger, J.C., Heat of formation for the formyl cation by photoionization mass spectrometry, Int. J. Mass Spectrom. Ion Processes, 1985, 66, 271. [all data]

Bell, Ng, et al., 1975
Bell, S.; Ng, T.L.; Walsh, A.D., Vacuum ultraviolet spectra of formic and acetic acids, J. Chem. Soc. Faraday Trans. 2, 1975, 71, 393. [all data]

Warneck, 1974
Warneck, P., Heat of formation of the HCO radical, Z. Naturforsch. A:, 1974, 29, 350. [all data]

Knowles and Nicholson, 1974
Knowles, D.J.; Nicholson, A.J.C., Ionization energies of formic and acetic acid monomers, J. Chem. Phys., 1974, 60, 1180. [all data]

Watanabe, Yokoyama, et al., 1973
Watanabe, I.; Yokoyama, Y.; Ikeda, S., Vibrational structures in the photoelectron spectrum of formic acid, Chem. Phys. Lett., 1973, 19, 406. [all data]

Watanabe, Yokoyama, et al., 1973, 2
Watanabe, I.; Yokoyama, Y.; Ikeda, S., Lone pair ionization potentials of carboxylic acids determined by He(I) photoelectron spectroscopy, Bull. Chem. Soc. Jpn., 1973, 46, 1959. [all data]

Thomas, 1972
Thomas, R.K., Photoelectron spectroscopy of hydrogen-bonded systems: spectra of monomers, dimers and mixed complexes of carboxylic acides, Proc. R. Soc. London A:, 1972, 331, 249. [all data]

Matthews and Warneck, 1969
Matthews, C.S.; Warneck, P., Heats of formation of CHO⁺ and C₃H₃⁺ by photoionization, J. Chem. Phys. 5, 1969, 1, 854. [all data]

Brundle, Turner, et al., 1969
Brundle, C.R.; Turner, D.W.; Robin, M.B.; Basch, H., Photoelectron spectroscopy of simple amides and carboxylic acids, Chem. Phys. Lett., 1969, 3, 292. [all data]

Vilesov, 1960
Vilesov, F.I., The photoionization of vapors of compounds whose molecules contain carbonyl groups, Dokl. Phys. Chem., 1960, 132, 521, In original 1332. [all data]

Watanabe, 1957
Watanabe, K., Ionization potentials of some molecules, J. Chem. Phys., 1957, 26, 542. [all data]

Price and Evans, 1937
Price, W.C.; Evans, W.M., The absorption spectrum of formic acid in the vacuum ultra-violet, Proc. Roy. Soc. (London), 1937, A162, 110. [all data]

Von Niessen, Bieri, et al., 1980
Von Niessen, W.; Bieri, G.; Asbrink, L., 30.4 nm He(II) photoelectron spectra of organic molecules. Part III. Oxo-compounds (C,H,O), J. Electron Spectrosc. Relat. Phenom., 1980, 21, 175. [all data]

Benoit and Harrison, 1977
Benoit, F.M.; Harrison, A.G., Predictive value of proton affinity. Ionization energy correlations involving oxygenated molecules, J. Am. Chem. Soc., 1977, 99, 3980. [all data]

Rao, 1975
Rao, C.N.R., Lone-pair ionization bands of chromophores in the photoelectron spectra of organic molecules, Indian J. Chem., 1975, 13, 950. [all data]

Kimura, Katsumata, et al., 1975
Kimura, K.; Katsumata, S.; Yamazaki, T.; Wakabayashi, H., UV photoelectron spectra and sum rule consideration; out-of-plane orbitals of unsaturated compounds with planar-skeleton structure, J. Electron Spectrosc. Relat. Phenom., 1975, 6, 41. [all data]

Stepanov, Perov, et al., 1988
Stepanov, A.N.; Perov, A.A.; Kabanov, S.P.; Simonov, A.P., Formation of long-lived, highly excited atoms during dissociative excitation of CH₃CN, CH₃CH₂OH, CH₃COOH, HCOOH, and C₄H₄S molecules on electron impact, Russ. J. Phys. Chem., 1988, 22, 81. [all data]

Golovin, Akopyan, et al., 1979
Golovin, A.V.; Akopyan, M.E.; Vilesov, F.I.; Sergeev, Y.L., Ion-electron coincidence study of the photoionization of formic and acetic acids, Khim. Vys. Energ., 1979, 13, 200. [all data]

Akopyan and Villem, 1976
Akopyan, M.E.; Villem, Ya.Ya., Ion-molecule reactions in the photoionization of formic and acetic acid vapors, High Energy Chem., 1976, 10, 24. [all data]

Notes

Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, References

• Symbols used in this document:
  

  AE	Appearance energy
  IE (evaluated)	Recommended ionization energy
  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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