Home Symbol which looks like a small house Up Solid circle with an upward pointer in it

Acetic acid, cyano-, methyl ester

Data at NIST subscription sites:

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.


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:
B - John E. Bartmess
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

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

C4H4NO2- + Hydrogen cation = Acetic acid, cyano-, methyl ester

By formula: C4H4NO2- + H+ = C4H5NO2

Quantity Value Units Method Reference Comment
Deltar1426. ± 8.8kJ/molG+TSMishima, Matsuoka, et al., 2004gas phase; Calc: keto form of acid more stable.; B
Deltar1425. ± 8.8kJ/molG+TSTaft, Abboud, et al., 1988gas phase; B
Quantity Value Units Method Reference Comment
Deltar1400. ± 8.4kJ/molIMREMishima, Matsuoka, et al., 2004gas phase; Calc: keto form of acid more stable.; B
Deltar1399. ± 8.4kJ/molIMRETaft, Abboud, et al., 1988gas phase; B

3,3,3-Trimethoxypropionitrile + Water = Acetic acid, cyano-, methyl ester + 2Methyl Alcohol

By formula: C6H11NO3 + H2O = C4H5NO2 + 2CH4O

Quantity Value Units Method Reference Comment
Deltar-25.7 ± 1.5kJ/molEqkGuthrie and Cullimore, 1980liquid phase; ALS

Acetic acid, cyano-, methyl ester + Water = Acetic acid, cyano- + Methyl Alcohol

By formula: C4H5NO2 + H2O = C3H3NO2 + CH4O

Quantity Value Units Method Reference Comment
Deltar-54. ± 2.kJ/molEqkGuthrie and Cullimore, 1980liquid 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.

Mishima, Matsuoka, et al., 2004
Mishima, M.; Matsuoka, M.; Lei, Y.X.; Rappoport, Z., Gas-phase acidities of disubstituted methanes and of enols of carboxamides substituted by electron-withdrawing groups, J. Org. Chem., 2004, 69, 18, 5947-5965, https://doi.org/10.1021/jo040196b . [all data]

Taft, Abboud, et al., 1988
Taft, R.W.; Abboud, J.L.M.; Anvia, F.; Berthelot, M.; Fujio, M.; Gal, J.-F.; Headley, A.D.; Henderson, W.G., Regarding the Inherent Dependence of Resonance Effects of Strongly Conjugated Substituents on Electron Demand, J. Am. Chem. Soc., 1988, 110, 6, 1797, https://doi.org/10.1021/ja00214a023 . [all data]

Guthrie and Cullimore, 1980
Guthrie, J.P.; Cullimore, P.A., Effect of the acyl substituent on the equilibrium constant for hydration of esters, Can. J. Chem., 1980, 58, 1281-1294. [all data]


Notes

Go To: Top, Reaction thermochemistry data, References