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:
  • Ion clustering data
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry data
  • Henry's Law data
  • Gas phase ion energetics data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • Vibrational and/or electronic energy levels
  • Gas Chromatography
• Data at other public NIST sites:
  • Computational Chemistry Comparison and Benchmark Database
  • Gas Phase Kinetics Database
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Ion clustering data

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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. Searches may be limited to ion clustering reactions. A general reaction search form is also available.

Clustering reactions

 +  = CH₂BrO₂^-

By formula: Br^- + CH₂O₂ = CH₂BrO₂^-

 +  = ( • )

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

( • ) +  = ( • 2)

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

( • 2) +  = ( • 3)

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

( • 3) +  = ( • 4)

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

( • 4) +  = ( • 5)

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

CH₂BrO₂^- + 2 = C₂H₄BrO₄^-

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

CH₂IO₂^- + 2 = C₂H₄IO₄^-

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

CH₂NO₅^- +  +  = CH₄NO₆^-

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

CH₅O⁺ +  = (CH₅O⁺ • )

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

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

CH₆N⁺ +  = (CH₆N⁺ • )

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

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

 +  = ( • )

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

( • ) +  = ( • 2)

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

( • 2) +  = ( • 3)

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

( • 3) +  = ( • 4)

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

( • 4) +  = ( • 5)

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

 +  = ( • )

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

 +  = ( • )

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

 +  = CH₂NO₅^-

By formula: NO₃^- + CH₂O₂ = CH₂NO₅^-

References

Go To: Top, Ion clustering data, Notes

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

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]

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]

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]

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]

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]

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]

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]

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]

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]

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]

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

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• 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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