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

NOTICE: Due to scheduled maintenance at our Gaithersburg campus, this site will not be available from 5:00 pm EDT (21:00 UTC) on Friday October 25 until 5:00 pm (21:00 UTC) on Sunday October 27. We apologize for any inconvenience this outage may cause.

Ethyl cyanoacetate

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.


Condensed phase thermochemistry 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 compiled as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity Value Units Method Reference Comment
Deltafliquid-330.3kJ/molCcbGuinchant, 1918Author hf288_condensed[kcal/mol]=-82.70 kcal/mol; ALS
Quantity Value Units Method Reference Comment
Deltacliquid-2638.kJ/molCcbGuinchant, 1918Author hf288_condensed[kcal/mol]=-82.70 kcal/mol; ALS
Quantity Value Units Method Reference Comment
liquid275.33J/mol*KN/AIskhakov, Ismailov, et al., 1991S value does not agree with 87 KHO/BUG.; DH
liquid177.45J/mol*KN/AKhodzhaeva, Bugakov, et al., 1987S value does not agree with 91ISK/ISM.; DH

Constant pressure heat capacity of liquid

Cp,liquid (J/mol*K) Temperature (K) Reference Comment
222.04300.Iskhakov, Ismailov, et al., 1991T = 90 to 300 K.; DH
220.22298.15Khodzhaeva, Bugakov, et al., 1987T = 90 to 300 K.; DH

Reaction thermochemistry data

Go To: Top, Condensed phase 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 compiled by: John E. Bartmess

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

C5H6NO2- + Hydrogen cation = Ethyl cyanoacetate

By formula: C5H6NO2- + H+ = C5H7NO2

Quantity Value Units Method Reference Comment
Deltar1422. ± 9.6kJ/molG+TSTaft and Bordwell, 1988gas phase
Quantity Value Units Method Reference Comment
Deltar1396. ± 8.4kJ/molIMRETaft and Bordwell, 1988gas phase

References

Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, Notes

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

Guinchant, 1918
Guinchant, M.J., Etude sur la fonction acide dans les derives metheniques et methiniques, Ann. Chem., 1918, 10, 30-84. [all data]

Iskhakov, Ismailov, et al., 1991
Iskhakov, B.G.; Ismailov, T.S.; Khodzhaeva, M.G.; Igamberdyev, Kh.T.; Mamadalimov, A.T., Heat capacity of cyanoacetic acid ethyl ester, Inzh.-Fiz. Zh., 1991, 61(3), 427-430. [all data]

Khodzhaeva, Bugakov, et al., 1987
Khodzhaeva, M.G.; Bugakov, Yu.V.; Ismailov, T.S., Heat capacity and thermodynamic functions of ethyl cyanoacetate, Khim.-Farm. Zhur., 1987, 21, 760-762. [all data]

Taft and Bordwell, 1988
Taft, R.W.; Bordwell, F.G., Structural and Solvent Effects Evaluated from Acidities Measured in Dimethyl Sulfoxide and in the Gas Phase, Acc. Chem. Res., 1988, 21, 12, 463, https://doi.org/10.1021/ar00156a005 . [all data]


Notes

Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, References