Acetamide
- Formula: C2H5NO
- Molecular weight: 59.0672
- IUPAC Standard InChI: InChI=1S/C2H5NO/c1-2(3)4/h1H3,(H2,3,4)
- IUPAC Standard InChIKey: DLFVBJFMPXGRIB-UHFFFAOYSA-N
- CAS Registry Number: 60-35-5
- Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
The 3d structure may be viewed using Java or Javascript. - Other names: Acetic acid amide; Ethanamide; Methanecarboxamide; CH3CONH2; NCI-C02108; Amid kyseliny octove
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Gas phase 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: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°gas | -56.96 ± 0.19 | kcal/mol | Ccb | Barnes and Pilcher, 1975 |
Condensed phase thermochemistry data
Go To: Top, Gas phase thermochemistry data, 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 |
|---|---|---|---|---|---|
| ΔfH°solid | -75.43 ± 0.20 | kcal/mol | Ccr | Nurachmetov, Beremzhanov, et al., 1985 | see Nurakhmeta, Beremzhanov, et al., 1984; ALS |
| ΔfH°solid | -74.11 | kcal/mol | Ccb | Ciocazanu, Dogaru, et al., 1976 | ALS |
| ΔfH°solid | -75.76 ± 0.17 | kcal/mol | Ccb | Barnes and Pilcher, 1975 | ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°solid | -283.47 ± 0.20 | kcal/mol | Ccr | Nurachmetov, Beremzhanov, et al., 1985 | see Nurakhmeta, Beremzhanov, et al., 1984; ALS |
| ΔcH°solid | -284.78 | kcal/mol | Ccb | Ciocazanu, Dogaru, et al., 1976 | ALS |
| ΔcH°solid | -283.13 ± 0.16 | kcal/mol | Ccb | Barnes and Pilcher, 1975 | ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| S°solid,1 bar | 27.49 | cal/mol*K | N/A | Nurachmetov, Beremzhanov, et al., 1985 | DH |
| S°solid,1 bar | 27.49 | cal/mol*K | N/A | Nurakhmetov, Beremzhanov, et al., 1984 | DH |
Constant pressure heat capacity of solid
| Cp,solid (cal/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 20.71 | 298. | Emons, Naumann, et al., 1986 | T = 298 to 400 K. Cp data given at 298 K as 1.467 kJ/kg*K (extrapolated). Cp = 1.481 + 0.0069(T-300) kJ/kg*K (300 to 330).; DH |
| 21.81 | 298.15 | Nurachmetov, Beremzhanov, et al., 1985 | T = 13 to 330 K.; DH |
| 21.81 | 298.15 | Nurakhmetov, Beremzhanov, et al., 1984 | T = 8 to 330 K.; DH |
| 21.51 | 300. | DeWit, DeKruif, et al., 1983 | T = 90 to 360 K.; DH |
| 21.6 | 298.15 | Skold, Suurkuusk, et al., 1976 | DH |
| 15.9 | 293. | Campbell and Campbell, 1940 | DH |
Reaction thermochemistry data
Go To: Top, Gas phase thermochemistry data, 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 as indicated in comments:
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
C2H4NO- + =
By formula: C2H4NO- + H+ = C2H5NO
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 362.0 ± 2.1 | kcal/mol | G+TS | Decouzon, Exner, et al., 1990 | gas phase; value altered from reference due to change in acidity scale; B |
| ΔrH° | 358.6 ± 1.2 | kcal/mol | EIAE | Muftakhov, Vasil'ev, et al., 1999 | gas phase; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 355.0 ± 2.0 | kcal/mol | IMRE | Decouzon, Exner, et al., 1990 | gas phase; value altered from reference due to change in acidity scale; B |
+
=
+
By formula: C4H7NO2 + H2O = C2H5NO + C2H4O2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -4.33 ± 0.05 | kcal/mol | Cm | Hill and Wadso, 1968 | solid phase; Heat of hydrolysis; ALS |
| ΔrH° | -4.33 ± 0.05 | kcal/mol | Cm | Wadso, 1965 | solid phase; Heat of hydrolysis; ALS |
C2H4NO- + =
By formula: C2H4NO- + H+ = C2H5NO
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 373.0 ± 3.1 | kcal/mol | G+TS | Hare, Marimanikkuppam, et al., 2001 | gas phase; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 365.0 ± 3.0 | kcal/mol | IMRB | Hare, Marimanikkuppam, et al., 2001 | gas phase; B |
+ 2
=
+ 2
By formula: C6H9NO3 + 2H2O = C2H5NO + 2C2H4O2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -24.74 ± 0.02 | kcal/mol | Cm | Hill and Wadso, 1968 | liquid phase; Heat of hydrolysis; ALS |
+
=
+
By formula: C2H5NO + H2O = C2H4O2 + H3N
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 18.2 ± 0.33 | kcal/mol | Cm | Hill and Wadso, 1968 | solid phase; Heat of hydrolysis; ALS |
+
=
+
By formula: HNaO + C2H5NO = C2H3NaO2 + H3N
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -10.9 | kcal/mol | Cm | Calvet, 1933 | solid phase; Heat of hydrolysis; ALS |
+
= (
•
)
By formula: Na+ + C2H5NO = (Na+ • C2H5NO)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 34.7 | kcal/mol | CIDT | Klassen, Anderson, et al., 1996 | RCD |
+
= (
•
)
By formula: K+ + C2H5NO = (K+ • C2H5NO)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 29.7 | kcal/mol | CIDT | Klassen, Anderson, et al., 1996 | RCD |
References
Go To: Top, Gas phase thermochemistry data, 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.
Barnes and Pilcher, 1975
Barnes, D.S.; Pilcher, G.,
Enthalpies of combustion of ethanamide, propanamide, and butanamide,
J. Chem. Thermodyn., 1975, 7, 377-382. [all data]
Nurachmetov, Beremzhanov, et al., 1985
Nurachmetov, N.N.; Beremzhanov, B.A.; Abramova, G.V.; Lebedev, B.V.,
Thermodynamics of (thio)amides and their compounds with mineral acids at (0-330)K,
Thermochim. Acta, 1985, 92, 329-332. [all data]
Nurakhmeta, Beremzhanov, et al., 1984
Nurakhmeta, N.N.; Beremzhanov, B.A.; Abramova, G.V.; Lebedev, B.V.,
Thermodynamic properties of acetamide, thio-semicarbazide, and thiourea hydronitrate at (0-330) K,
Probl. Kalorim. Khim. Termodin., Dokl. Vses. Konf., 10th, 1984, 2, 460-462. [all data]
Ciocazanu, Dogaru, et al., 1976
Ciocazanu, I.; Dogaru, V.; Zavoianu, D.,
Structure and reactivity of amides. Concerning the heats of combustion and formation of some unsaturated α, β amides derived from acetamide,
Rev. Chim. (Bucharest), 1976, 27, 4-6. [all data]
Nurakhmetov, Beremzhanov, et al., 1984
Nurakhmetov, N.N.; Beremzhanov, B.A.; Abramova, G.V.; Lebedev, B.V.,
Thermodynamic properties of acetamide, thiosemicarbazide, and thiourea hydronitrate at (0-330) K, Probl. Kalorim. Khim. Termodin., Dokl. Vses. Konf.,
10th, 1984, 2, 460-2. [all data]
Emons, Naumann, et al., 1986
Emons, H.H.; Naumann, R.; Jahn, K.; Flammersheim, H.J.,
Thermal properties of acetamide in the temperature range from 298 K to 400 K,
Thermochim. Acta, 1986, 104, 127-137. [all data]
DeWit, DeKruif, et al., 1983
DeWit, H.G.M.; DeKruif, C.G.; Van Miltenburg, J.C.,
Thermodynamic properties of molecular organic crystals containing organic crystals containing nitrogen, oxygen, and sulfur. II. Molar heat capacities of eight compounds by adiabatic calorimetry,
J. Chem. Thermodynam., 1983, 15, 891-902. [all data]
Skold, Suurkuusk, et al., 1976
Skold, R.; Suurkuusk, J.; Wadso, I.,
Thermochemistry of solutions of biochemical model compounds. 7. Aqueous solutions of some amides, t-butanol, and pentanol,
J. Chem. Thermodynam., 1976, 8, 1075-1080. [all data]
Campbell and Campbell, 1940
Campbell, A.N.; Campbell, A.J.R.,
The heats of solution, heats of formation,
specific heats and equilibrium diagrams of certain molecular compounds. J. Am. Chem. Soc., 1940, 62, 291-297. [all data]
Decouzon, Exner, et al., 1990
Decouzon, M.; Exner, O.; Gal, J.-F.; Maria, P.-C.,
The Gas-Phase Acidity and the Acidic Site of Acetohydroxamic Acid: an FT-ICR Study,
J. Org. Chem., 1990, 55, 13, 3980, https://doi.org/10.1021/jo00300a007
. [all data]
Muftakhov, Vasil'ev, et al., 1999
Muftakhov, M.V.; Vasil'ev, Y.V.; Mazunov, V.A.,
Determination of electron affinity of carbonyl radicals by means of negative ion mass spectrometry,
Rapid Commun. Mass Spectrom., 1999, 13, 12, 1104-1108, https://doi.org/10.1002/(SICI)1097-0231(19990630)13:12<1104::AID-RCM619>3.0.CO;2-C
. [all data]
Hill and Wadso, 1968
Hill, J.O.; Wadso, I.,
Some thermochemical properties of N,N,N-triacetylammonia,
Acta Chem. Scand., 1968, 22, 1590-1594. [all data]
Wadso, 1965
Wadso, I.,
Thermochemical properties of diacetimide, N-butyldiacetimide and N-phenyldiacetimide,
Acta Chem. Scand., 1965, 19, 1079-1087. [all data]
Hare, Marimanikkuppam, et al., 2001
Hare, M.C.; Marimanikkuppam, S.S.; Kass, S.R.,
Acetamide enolate: formation, reactivity, and proton affinity,
Int. J. Mass Spectrom., 2001, 210, 153-163, https://doi.org/10.1016/S1387-3806(01)00397-9
. [all data]
Calvet, 1933
Calvet, E.,
Mesures thermochimiques directes en chimie organique vitesses et chaleurs de saponification des amides. II.-Mesures effectuees et resultats obtenus,
J. Chim. Phys., 1933, 30, 140-146. [all data]
Klassen, Anderson, et al., 1996
Klassen, J.S.; Anderson, S.G.; Blades, A.T.; Kebarle, P.,
Reaction Enthalpies for M+L = M+ + L, Where M+ = Na+ and K+ and L = Acetamide, N-Methylacetamide, N,N-Dimethylacetamide, Glycine, and Glycylglycine, from Determinations of the Collision-Induced Dissociation Thresholds,
J. Phys. Chem., 1996, 100, 33, 14218, https://doi.org/10.1021/jp9608382
. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, References
- Symbols used in this document:
Cp,solid Constant pressure heat capacity of solid S°solid,1 bar Entropy of solid at standard conditions (1 bar) ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°solid Enthalpy of formation of solid at standard conditions ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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