Methaneperoxoic acid


Reaction thermochemistry 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 by: John E. Bartmess

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Individual Reactions

CHO3- + Hydrogen cation = Methaneperoxoic acid

By formula: CHO3- + H+ = CH2O3

Quantity Value Units Method Reference Comment
Δr1467. ± 14.kJ/molG+TSVillano, Eyet, et al., 2010gas phase; Between HOAc, tBuSH. For less-stable (+3.3 kcal) non-H-bonded) isomer of acid
Δr<1551. ± 9.2kJ/molG+TSBowie, DePuy, et al., 1986gas phase; More acidic than acetone. Formed from DMF + HOO-; oxidises NO to NO2. Computations indicate HOF(A-) ca. -77, dHacid ca. 349 kcal/m
Quantity Value Units Method Reference Comment
Δr1439. ± 14.kJ/molIMRBVillano, Eyet, et al., 2010gas phase; Between HOAc, tBuSH. For less-stable (+3.3 kcal) non-H-bonded) isomer of acid
Δr<1523. ± 8.4kJ/molIMRBBowie, DePuy, et al., 1986gas phase; More acidic than acetone. Formed from DMF + HOO-; oxidises NO to NO2. Computations indicate HOF(A-) ca. -77, dHacid ca. 349 kcal/m

Gas phase ion energetics 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 by: John E. Bartmess

De-protonation reactions

CHO3- + Hydrogen cation = Methaneperoxoic acid

By formula: CHO3- + H+ = CH2O3

Quantity Value Units Method Reference Comment
Δr1467. ± 14.kJ/molG+TSVillano, Eyet, et al., 2010gas phase; Between HOAc, tBuSH. For less-stable (+3.3 kcal) non-H-bonded) isomer of acid
Δr<1551. ± 9.2kJ/molG+TSBowie, DePuy, et al., 1986gas phase; More acidic than acetone. Formed from DMF + HOO-; oxidises NO to NO2. Computations indicate HOF(A-) ca. -77, dHacid ca. 349 kcal/m
Quantity Value Units Method Reference Comment
Δr1439. ± 14.kJ/molIMRBVillano, Eyet, et al., 2010gas phase; Between HOAc, tBuSH. For less-stable (+3.3 kcal) non-H-bonded) isomer of acid
Δr<1523. ± 8.4kJ/molIMRBBowie, DePuy, et al., 1986gas phase; More acidic than acetone. Formed from DMF + HOO-; oxidises NO to NO2. Computations indicate HOF(A-) ca. -77, dHacid ca. 349 kcal/m

Vibrational and/or electronic energy levels

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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 by: Marilyn E. Jacox

State:   X


Vib. 
sym. 
 No.   Approximate 
 type of mode 
 cm-1   Med.   Method   References

a' 1 OH stretch 3340.7 w gas IR Giguere and Olmos, 1952
Maker, Niki, et al., 1977
1 OH stretch 3334.0 m Ar IR Tyblewski, Dommen, et al., 1991
2 CH stretch 2977 w T gas IR Giguere and Olmos, 1952
2 CH stretch 2964.0 w Ar IR Tyblewski, Dommen, et al., 1991
3 C=O stretch 1744.7 vs gas IR Giguere and Olmos, 1952
Maker, Niki, et al., 1977
3 C=O stretch 1737.3 s Ar IR Tyblewski, Dommen, et al., 1991
4 OH bend 1442 s T gas IR Giguere and Olmos, 1952
4 OH bend 1437.4 s Ar IR Tyblewski, Dommen, et al., 1991
5 Mixed 1340 w T gas IR Giguere and Olmos, 1952
5 Mixed 1334.6 m Ar IR Tyblewski, Dommen, et al., 1991
6 C-O stretch 1124.98 vs gas IR Giguere and Olmos, 1952
Maker, Niki, et al., 1977
Bauder, Dommen, et al., 1990
6 C-O stretch 1113.9 s Ar IR Tyblewski, Dommen, et al., 1991
7 Mixed 859 w gas IR Giguere and Olmos, 1952
7 Mixed 857.0 m Ar IR Tyblewski, Dommen, et al., 1991
8 O-O stretch 810 w gas IR Giguere and Olmos, 1952
8 O-O stretch 810.6 m Ar IR Tyblewski, Dommen, et al., 1991
9 Skel. deform. 336.3 m Ar IR Tyblewski, Dommen, et al., 1991
a 11 Torsion 441.3 s Ar IR Tyblewski, Dommen, et al., 1991
12 Torsion 331.6 m Ar IR Tyblewski, Dommen, et al., 1991

Additional references: Jacox, 1994, page 336; Oldani, Ha, et al., 1983

Notes

wWeak
mMedium
sStrong
vsVery strong
TTentative assignment or approximate value

References

Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, Vibrational and/or electronic energy levels, Notes

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

Villano, Eyet, et al., 2010
Villano, S.M.; Eyet, N.; Wren, S.W.; Ellison, G.B.; Bierbaum, V.M.; Lineberger, W.C., Photoelectron Spectroscopy and Thermochemistry of the Peroxyformate Anion, J. Phys. Chem. A, 2010, 114, 1, 191-200, https://doi.org/10.1021/jp907569w . [all data]

Bowie, DePuy, et al., 1986
Bowie, J.H.; DePuy, C.H.; Sullivan, S.A.; Berbaum, V.M., Gas phase reactions of the hydroperoxide and peroxyformate anions, Can. J. Chem., 1986, 64, 1046. [all data]

Giguere and Olmos, 1952
Giguere, P.A.; Olmos, A.W., A SPECTROSCOPIC STUDY OF HYDROGEN BONDING IN PERFORMIC AND PERACETIC ACIDS, Can. J. Chem., 1952, 30, 11, 821, https://doi.org/10.1139/v52-099 . [all data]

Maker, Niki, et al., 1977
Maker, P.D.; Niki, H.; Savage, C.M.; Breitenbach, L.P., Fourier transform infrared spectrometric determination of gaseous performic acid, Anal. Chem., 1977, 49, 9, 1346, https://doi.org/10.1021/ac50017a016 . [all data]

Tyblewski, Dommen, et al., 1991
Tyblewski, M.; Dommen, J.; Ha, T.-K.; Bauder, A., Spectrochim. Acta, 1991, 47A, 397. [all data]

Bauder, Dommen, et al., 1990
Bauder, A.; Dommen, J.; Hollenstein, H.; Luckhaus, D.; Quack, M., The ν6 fundamental band of peroxyformic acid near 1125 cm-1, J. Mol. Spectrosc., 1990, 143, 2, 268, https://doi.org/10.1016/0022-2852(91)90091-N . [all data]

Jacox, 1994
Jacox, M.E., Vibrational and electronic energy levels of polyatomic transient molecules, American Chemical Society, Washington, DC, 1994, 464. [all data]

Oldani, Ha, et al., 1983
Oldani, M.; Ha, T.-K.; Bauder, A., Microwave spectrum, dipole moment, and substitution structure of peroxyformic acid, J. Am. Chem. Soc., 1983, 105, 3, 360, https://doi.org/10.1021/ja00341a011 . [all data]


Notes

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