Ethanediamide

Formula: C₂H₄N₂O₂
Molecular weight: 88.0654
IUPAC Standard InChI: InChI=1S/C2H4N2O2/c3-1(5)2(4)6/h(H2,3,5)(H2,4,6)
IUPAC Standard InChIKey: YIKSCQDJHCMVMK-UHFFFAOYSA-N
CAS Registry Number: 471-46-5
Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
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Other names: Oxalamide; Oxalic acid diamide; Oxamide; Oxamimidic acid; NH2COCONH2; Amid kyseliny stavelove; Formimidic acid, 1-carbamoyl-; Oxamid; Diaminoglyoxal; Oxamic acid amide; NSC 2770
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Information on this page:
Other data available:
- Gas phase ion energetics data
- Mass spectrum (electron ionization)
Data at other public NIST sites:
- X-ray Photoelectron Spectroscopy Database, version 5.0
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Gas phase thermochemistry data

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Data compiled by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity	Value	Units	Method	Reference	Comment
Δ_fH°_gas	-92.52 ± 0.31	kcal/mol	Ccr	Nunez, Barral, et al., 1988	Author was aware that data differs from previously reported values

Condensed phase thermochemistry data

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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
Δ_fH°_solid	-109.2	kcal/mol	Ccb	Parkhomenko, Pivovarov, et al., 1990	Author was aware that data differs from previously reported values; ALS
Δ_fH°_solid	-120.6 ± 0.1	kcal/mol	Ccr	Nunez, Barral, et al., 1988	Author was aware that data differs from previously reported values; ALS
Δ_fH°_solid	-123.2 ± 1.0	kcal/mol	Ccb	Tavernier and Lamouroux, 1957	Reanalyzed by Cox and Pilcher, 1970, Original value = -122.679 kcal/mol; Author's hf298_condensed=-123.705 kcal/mol; ALS
Quantity	Value	Units	Method	Reference	Comment
Δ_cH°_solid	-215.7	kcal/mol	Ccb	Parkhomenko, Pivovarov, et al., 1990	Author was aware that data differs from previously reported values; ALS
Δ_cH°_solid	-204.2 ± 0.1	kcal/mol	Ccr	Nunez, Barral, et al., 1988	Author was aware that data differs from previously reported values; ALS
Δ_cH°_solid	-201.5 ± 1.0	kcal/mol	Ccb	Tavernier and Lamouroux, 1957	Reanalyzed by Cox and Pilcher, 1970, Original value = -202.055 kcal/mol; Author's hf298_condensed=-123.705 kcal/mol; ALS
Δ_cH°_solid	-203.97	kcal/mol	Ccb	Handrick, 1956	ALS
Quantity	Value	Units	Method	Reference	Comment
S°_{solid,1 bar}	28.229	cal/mol*K	N/A	Egan, Wakefield, et al., 1965	DH

Constant pressure heat capacity of solid

C_p,solid (cal/mol*K)	Temperature (K)	Reference	Comment
27.220	298.15	Egan, Wakefield, et al., 1965	T = 10 to 310 K.; DH

Phase change data

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Data compiled as indicated in comments:
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity	Value	Units	Method	Reference	Comment
Δ_subH°	28.04 ± 0.29	kcal/mol	TE,ME	Nunez, Barral, et al., 1988	AC
Δ_subH°	27.000	kcal/mol	V	Bradley and Cleasby, 1953	ALS

Enthalpy of sublimation

Δ_subH (kcal/mol)	Temperature (K)	Method	Reference	Comment
27.68	387.	TE,ME	De Wit, Van Miltenburg, et al., 1983	Based on data from 370. to 398. K.; AC
27.0	361.	ME	Bradley and Cleasby, 1953, 2	Based on data from 353. to 369. K. See also Jones, 1960 and Cox and Pilcher, 1970, 2.; AC

References

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Nunez, Barral, et al., 1988
Nunez, L.; Barral, L.; Pilcher, G., Enthalpies of combustion of oxamic acid, oxamide, and dithiooxamide, J. Chem. Thermodyn., 1988, 20, 1211-1216. [all data]

Parkhomenko, Pivovarov, et al., 1990
Parkhomenko, V.D.; Pivovarov, A.A.; Sytnik, S.V., Thermophysical properties of oxide, Izv. Vyssh. Uchebn. Zaved., Khim. Khim. Tekhnol., 1990, 33, 53-55. [all data]

Tavernier and Lamouroux, 1957
Tavernier, P.; Lamouroux, M., Determinations calorimetriques relatives a vingt et une substances organiques, Mem. Poudres, 1957, 39, 335-356. [all data]

Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]

Handrick, 1956
Handrick, G.R., Report of the study of pure explosive compounds. Part IV. Calculation of heat of combustion of organic compounds from structural features and calculation of power of high explosives, Rpt. C-58247 for the Office of the Chief of Ordnance, contract DA-19-020-ORD-47 by the Arthur D. Little, Inc., Cambridge, MA, 1956, 467-573. [all data]

Egan, Wakefield, et al., 1965
Egan, E.P.; Wakefield, Z.T.; Farr, T.D., Low temperature heat capacity and entropy of oxamide, 10-310 K, J. Chem. Eng. Data, 1965, 10, 138-140. [all data]

Bradley and Cleasby, 1953
Bradley, R.S.; Cleasby, T.G., The vapour pressure and lattice energy of hydrogen-bonded crystals. Part I. Oxamide, oxamic acid, and rubeanie acid, J. Chem. Soc., 1953, 1681-16. [all data]

De Wit, Van Miltenburg, et al., 1983
De Wit, H.G.M.; Van Miltenburg, J.C.; De Kruif, C.G., Thermodynamic properties of molecular organic crystals containing nitrogen, oxygen, and sulphur 1. Vapour pressures and enthalpies of sublimation, The Journal of Chemical Thermodynamics, 1983, 15, 7, 651-663, https://doi.org/10.1016/0021-9614(83)90079-4 . [all data]

Bradley and Cleasby, 1953, 2
Bradley, R.S.; Cleasby, T.G., 349. The vapour pressure and lattice energy of some aromatic ring compounds, J. Chem. Soc., 1953, 1690, https://doi.org/10.1039/jr9530001690 . [all data]

Jones, 1960
Jones, A.H., Sublimation Pressure Data for Organic Compounds., J. Chem. Eng. Data, 1960, 5, 2, 196-200, https://doi.org/10.1021/je60006a019 . [all data]

Cox and Pilcher, 1970, 2
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press Inc., London, 1970, 643. [all data]

Notes

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Symbols used in this document:

C_p,solid	Constant pressure heat capacity of solid
S°_{solid,1 bar}	Entropy of solid at standard conditions (1 bar)
Δ_cH°_solid	Enthalpy of combustion of solid at standard conditions
Δ_fH°_gas	Enthalpy of formation of gas at standard conditions
Δ_fH°_solid	Enthalpy of formation of solid at standard conditions
Δ_subH	Enthalpy of sublimation
Δ_subH°	Enthalpy of sublimation at standard conditions

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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