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Formaldehyde

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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:
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
B - John E. Bartmess
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

CH2OH+ + Formaldehyde = (CH2OH+ bullet Formaldehyde)

By formula: CH3O+ + CH2O = (CH3O+ bullet CH2O)

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

Quantity Value Units Method Reference Comment
Deltar27.7kcal/molICRLarson and McMahon, 1982gas phase; switching reaction(H3O+)H2O, Entropy change calculated or estimated; Cunningham, Payzant, et al., 1972, Lias, Liebman, et al., 1984, Keesee and Castleman, 1986; M
Deltar29.5kcal/molFAFehsenfeld, Dotan, et al., 1978gas phase; From thermochemical cycle,switching reaction(H3O+)H2O; Lias, Liebman, et al., 1984, Meot-Ner (Mautner), 1992; M
Deltar27.7kcal/molICRLarson, Clair, et al., 1982gas phase; From thermochemical cycle,switching reaction(H2O/H2CO), Entropy change calculated or estimated; Cunningham, Payzant, et al., 1972, Lias, Liebman, et al., 1984; M
Quantity Value Units Method Reference Comment
Deltar26.5cal/mol*KN/ALarson and McMahon, 1982gas phase; switching reaction(H3O+)H2O, Entropy change calculated or estimated; Cunningham, Payzant, et al., 1972, Lias, Liebman, et al., 1984, Keesee and Castleman, 1986; M
Deltar27.5cal/mol*KFAFehsenfeld, Dotan, et al., 1978gas phase; From thermochemical cycle,switching reaction(H3O+)H2O; Lias, Liebman, et al., 1984, Meot-Ner (Mautner), 1992; M
Deltar26.5cal/mol*KN/ALarson, Clair, et al., 1982gas phase; From thermochemical cycle,switching reaction(H2O/H2CO), Entropy change calculated or estimated; Cunningham, Payzant, et al., 1972, Lias, Liebman, et al., 1984; M
Quantity Value Units Method Reference Comment
Deltar19.8kcal/molICRLarson and McMahon, 1982gas phase; switching reaction(H3O+)H2O, Entropy change calculated or estimated; Cunningham, Payzant, et al., 1972, Lias, Liebman, et al., 1984, Keesee and Castleman, 1986; M
Deltar19.8kcal/molICRLarson, Clair, et al., 1982gas phase; From thermochemical cycle,switching reaction(H2O/H2CO), Entropy change calculated or estimated; Cunningham, Payzant, et al., 1972, Lias, Liebman, et al., 1984; M

Lithium ion (1+) + Formaldehyde = (Lithium ion (1+) bullet Formaldehyde)

By formula: Li+ + CH2O = (Li+ bullet CH2O)

Quantity Value Units Method Reference Comment
Deltar36.0kcal/molICRWoodin and Beauchamp, 1978gas phase; switching reaction(Li+)H2O, Entropy change calculated or estimated; Dzidic and Kebarle, 1970 interpolated; M
Deltar36.kcal/molICRStaley and Beauchamp, 1975gas phase; switching reaction(Li+)H2O, from graph; Dzidic and Kebarle, 1970 extrapolated; M
Quantity Value Units Method Reference Comment
Deltar26.cal/mol*KN/AWoodin and Beauchamp, 1978gas phase; switching reaction(Li+)H2O, Entropy change calculated or estimated; Dzidic and Kebarle, 1970 interpolated; M
Quantity Value Units Method Reference Comment
Deltar28.2kcal/molICRWoodin and Beauchamp, 1978gas phase; switching reaction(Li+)H2O, Entropy change calculated or estimated; Dzidic and Kebarle, 1970 interpolated; M

(CH3O- bullet 4294967295Formaldehyde) + Formaldehyde = CH3O-

By formula: (CH3O- bullet 4294967295CH2O) + CH2O = CH3O-

Quantity Value Units Method Reference Comment
Deltar39.90 ± 0.51kcal/molN/ANee, Osterwalder, et al., 2006gas phase; B
Deltar40.8 ± 1.1kcal/molTherOsborn, Leahy, et al., 1998gas phase; B
Deltar41.8 ± 2.2kcal/molTherBartmess, Scott, et al., 1979gas phase; The acidity is 1.2 kcal/mol stronger than that from the D-EA cycle, due to the multi-compound fit for the acidity scale.; value altered from reference due to change in acidity scale; B

CHO- + Hydrogen cation = Formaldehyde

By formula: CHO- + H+ = CH2O

Quantity Value Units Method Reference Comment
Deltar394.52 ± 0.23kcal/molD-EAMurray, Miller, et al., 1986gas phase; B
Quantity Value Units Method Reference Comment
Deltar386.65 ± 0.40kcal/molH-TSMurray, Miller, et al., 1986gas phase; B
Deltar394.0 ± 4.5kcal/molIMRBKarpas and Klein, 1975gas phase; B

CH2N+ + Formaldehyde = (CH2N+ bullet Formaldehyde)

By formula: CH2N+ + CH2O = (CH2N+ bullet CH2O)

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

Quantity Value Units Method Reference Comment
Deltar21.8kcal/molFATanaka, Mackay, et al., 1978gas phase; switching reaction(HCNH+)HCN; Meot-Ner (Mautner), 1978; M

(dimethylamino)methanol = Dimethylamine + Formaldehyde

By formula: C3H9NO = C2H7N + CH2O

Quantity Value Units Method Reference Comment
Deltar30.2 ± 0.2kcal/molCmRogers and Rapiejko, 1974liquid phase; Heat of formation derived by 77PED/RYL; ALS

Methylal + Water = Formaldehyde + 2Methyl Alcohol

By formula: C3H8O2 + H2O = CH2O + 2CH4O

Quantity Value Units Method Reference Comment
Deltar18.45 ± 0.12kcal/molCmBirley and Skinner, 1970liquid phase; Heat of hydrolysis; ALS

Formaldehyde + Urea, N,N-dimethyl- = Urea, 3-(hydroxymethyl)-1,1-dimethyl-

By formula: CH2O + C3H8N2O = C4H10N2O2

Quantity Value Units Method Reference Comment
Deltar-4.8 ± 0.2kcal/molKinPerepelkova, Igranova, et al., 1981liquid phase; solvent: Phosphate buffer; ALS

2Dimethylamine + Formaldehyde = Methanediamine, N,N,N',N'-tetramethyl- + Water

By formula: 2C2H7N + CH2O = C5H14N2 + H2O

Quantity Value Units Method Reference Comment
Deltar-45.6 ± 0.6kcal/molCmRogers and Rapiejko, 1974gas phase; ALS

(Iron ion (1+) bullet 2Formaldehyde) + Formaldehyde = (Iron ion (1+) bullet 3Formaldehyde)

By formula: (Fe+ bullet 2CH2O) + CH2O = (Fe+ bullet 3CH2O)

Quantity Value Units Method Reference Comment
Deltar18.2 ± 1.0kcal/molCIDTRodgers and Armentrout, 2000RCD

(Iron ion (1+) bullet 3Formaldehyde) + Formaldehyde = (Iron ion (1+) bullet 4Formaldehyde)

By formula: (Fe+ bullet 3CH2O) + CH2O = (Fe+ bullet 4CH2O)

Quantity Value Units Method Reference Comment
Deltar12.0 ± 1.7kcal/molCIDTRodgers and Armentrout, 2000RCD

(Iron ion (1+) bullet Formaldehyde) + Formaldehyde = (Iron ion (1+) bullet 2Formaldehyde)

By formula: (Fe+ bullet CH2O) + CH2O = (Fe+ bullet 2CH2O)

Quantity Value Units Method Reference Comment
Deltar39.2 ± 1.0kcal/molCIDTRodgers and Armentrout, 2000RCD

Dimethylamine + Formaldehyde = (dimethylamino)methanol

By formula: C2H7N + CH2O = C3H9NO

Quantity Value Units Method Reference Comment
Deltar-30.2 ± 0.2kcal/molCmRogers and Rapiejko, 1974gas phase; ALS

Hydrogen + Carbon monoxide = Formaldehyde

By formula: H2 + CO = CH2O

Quantity Value Units Method Reference Comment
Deltar-2.90kcal/molEqkNewton and Dodge, 1933gas phase; ALS

Iron ion (1+) + Formaldehyde = (Iron ion (1+) bullet Formaldehyde)

By formula: Fe+ + CH2O = (Fe+ bullet CH2O)

Quantity Value Units Method Reference Comment
Deltar33.0 ± 1.7kcal/molCIDTRodgers and Armentrout, 2000RCD

Aluminum ion (1+) + Formaldehyde = (Aluminum ion (1+) bullet Formaldehyde)

By formula: Al+ + CH2O = (Al+ bullet CH2O)

Quantity Value Units Method Reference Comment
Deltar27.5 ± 2.4kcal/molEqGBouchard, Brenner, et al., 1997RCD

1,3,5-Trioxane = 3Formaldehyde

By formula: C3H6O3 = 3CH2O

Quantity Value Units Method Reference Comment
Deltar46.37 ± 0.60kcal/molEqkBusfield and Merigold, 1969solid phase; ALS

3Formaldehyde = 1,3,5-Trioxane

By formula: 3CH2O = C3H6O3

Quantity Value Units Method Reference Comment
Deltar-33.27 ± 0.50kcal/molEqkBusfield and Merigold, 1969gas phase; ALS

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.

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]

Cunningham, Payzant, et al., 1972
Cunningham, A.J.; Payzant, J.D.; Kebarle, P., A Kinetic Study of the Proton Hydrate H+(H2O)n Equilibria in the Gas Phase, J. Am. Chem. Soc., 1972, 94, 22, 7627, https://doi.org/10.1021/ja00777a003 . [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]

Fehsenfeld, Dotan, et al., 1978
Fehsenfeld, F.C.; Dotan, I.; Albritton, D.L.; Howard, C.J.; Ferguson, E.E., Stratospheric Positive Ion Chemistry of Formaldehyde and Methanol, J. Geophys. Res., 1978, 83, C3, 1333, https://doi.org/10.1029/JC083iC03p01333 . [all data]

Meot-Ner (Mautner), 1992
Meot-Ner (Mautner), M., Intermolecular Forces in Organic Clusters, J. Am. Chem. Soc., 1992, 114, 9, 3312, https://doi.org/10.1021/ja00035a024 . [all data]

Larson, Clair, et al., 1982
Larson, J.W.; Clair, R.L.; McMahon, T.B., Bimolecular Production of Proton Bound Dimers in the Gas Phase. A Low Pressure Ion Cyclotron Resonance Technique for Examination of Solvent Exchange Equilibria and Determination of Single Molecule Solvation Energetics, Can. J. Chem., 1982, 60, 4, 542, https://doi.org/10.1139/v82-079 . [all data]

Woodin and Beauchamp, 1978
Woodin, R.L.; Beauchamp, J.L., Bonding of Li+ to Lewis Bases in the Gas Phase. Reversals in Methyl Substituent Effects for Different Reference Acids, J. Am. Chem. Soc., 1978, 100, 2, 501, https://doi.org/10.1021/ja00470a024 . [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]

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]

Nee, Osterwalder, et al., 2006
Nee, M.J.; Osterwalder, A.; Zhou, J.; Neumark, D.M., Slow electron velocity-map imaging photoelectron spectra of the methoxide anion, J. Chem. Phys., 2006, 125, 1, 014306, https://doi.org/10.1063/1.2212411 . [all data]

Osborn, Leahy, et al., 1998
Osborn, D.L.; Leahy, D.J.; Kim, E.H.; deBeer, E.; Neumark, D.M., Photoelectron spectroscopy of CH3O- and CD3O-, Chem. Phys. Lett., 1998, 292, 4-6, 651-655, https://doi.org/10.1016/S0009-2614(98)00717-9 . [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]

Murray, Miller, et al., 1986
Murray, K.K.; Miller, T.M.; Leopold, D.G.; Lineberger, W.C., Laser photoelectron spectroscopy of the Formylf anion, J. Chem. Phys., 1986, 84, 2520. [all data]

Karpas and Klein, 1975
Karpas, Z.; Klein, F.S., Negative ion-molecule reactions in a mixture of ammonia-formaldehyde - an ICR mass spectrometry study, Int. J. Mass Spectrom. Ion Phys., 1975, 18, 65. [all data]

Tanaka, Mackay, et al., 1978
Tanaka, K.; Mackay, G.I.; Bohme, D.K., Rate and Equilibrium Constant Measurements for Gas-Phase Proton-Transfer Reactions Involving H2O, H2S, HCN, and H2CO, Can. J. Chem., 1978, 56, 2, 193, https://doi.org/10.1139/v78-031 . [all data]

Meot-Ner (Mautner), 1978
Meot-Ner (Mautner), M., Solvation of the Proton by HCN and CH3CN. Condensation of HCN with Ions in the Gas Phase., J. Am. Chem. Soc., 1978, 100, 15, 4694, https://doi.org/10.1021/ja00483a012 . [all data]

Rogers and Rapiejko, 1974
Rogers, F.E.; Rapiejko, R.J., Thermochemistry of carbonyl addition reactions. II. Enthalpy of addition of dimethylamine to formaldehyde, J. Phys. Chem., 1974, 78, 599-603. [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]

Perepelkova, Igranova, et al., 1981
Perepelkova, T.I.; Igranova, E.G.; Moiseev, V.D.; Demchenko, L.Ya.; Zhuravleva, I.I., Calorimetric study of the methylolation of 1,1-dimethylurea, Khim. Promst. Ser. Proizvod. Pererab. Plastmass Sint. Smol, 1981, 15-18. [all data]

Rodgers and Armentrout, 2000
Rodgers, M.T.; Armentrout, P.B., Noncovalent Metal-Ligand Bond Energies as Studied by Threshold Collision-Induced Dissociation, Mass Spectrom. Rev., 2000, 19, 4, 215, https://doi.org/10.1002/1098-2787(200007)19:4<215::AID-MAS2>3.0.CO;2-X . [all data]

Newton and Dodge, 1933
Newton, R.H.; Dodge, B.F., The equilibrium between carbon monoxide, hydrogen, formaldehyde and methanol. I. The reactions CO + H2 = HCOH and H2 + HCOH = CH3OH, J. Am. Chem. Soc., 1933, 55, 4747-4759. [all data]

Bouchard, Brenner, et al., 1997
Bouchard, F.; Brenner, V.; Carra, C.; Hepburn, J.W.; Koyanagi, G.K.; McMahon, T.B.; Ohanessian, G.; Peschke, M., Energetics and Structure of Complexes of Al+ with Small Organic Molecules in the Gas Phase, J. Phys. Chem. A, 1997, 101, 33, 5885, https://doi.org/10.1021/jp9703465 . [all data]

Busfield and Merigold, 1969
Busfield, W.K.; Merigold, D., The gas-phase equilibrium between trioxan and formaldehyde: The standard enthalpy and entropy of the trimerisation of formaldehyde, J. Chem. Soc. A, 1969, 19, 2975-2977. [all data]


Notes

Go To: Top, Reaction thermochemistry data, References