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
View 3d structure (requires JavaScript / HTML 5) - 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 | -238.33 ± 0.78 | kJ/mol | Ccb | Barnes and Pilcher, 1975 |
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 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° | 1515. ± 8.8 | kJ/mol | G+TS | Decouzon, Exner, et al., 1990 | gas phase; value altered from reference due to change in acidity scale; B |
| ΔrH° | 1500. ± 5.0 | kJ/mol | EIAE | Muftakhov, Vasil'ev, et al., 1999 | gas phase; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 1485. ± 8.4 | kJ/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° | -18.1 ± 0.2 | kJ/mol | Cm | Hill and Wadso, 1968 | solid phase; Heat of hydrolysis; ALS |
| ΔrH° | -18.1 ± 0.2 | kJ/mol | Cm | Wadso, 1965 | solid phase; Heat of hydrolysis; ALS |
C2H4NO- + =
By formula: C2H4NO- + H+ = C2H5NO
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 1561. ± 13. | kJ/mol | G+TS | Hare, Marimanikkuppam, et al., 2001 | gas phase; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 1527. ± 13. | kJ/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° | -103.5 ± 0.08 | kJ/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° | 76.1 ± 1.4 | kJ/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° | -45.6 | kJ/mol | Cm | Calvet, 1933 | solid phase; Heat of hydrolysis; ALS |
+
= (
•
)
By formula: Na+ + C2H5NO = (Na+ • C2H5NO)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 145. | kJ/mol | CIDT | Klassen, Anderson, et al., 1996 | RCD |
+
= (
•
)
By formula: K+ + C2H5NO = (K+ • C2H5NO)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 124. | kJ/mol | CIDT | Klassen, Anderson, et al., 1996 | RCD |
Gas Chromatography
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 by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Van Den Dool and Kratz RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | SPB-Sulfur | 719.8 | de Lacy Costello, Evans, et al., 2001 | 30. m/0.32 mm/4. μm, 40. C @ 12.5 min, 4. K/min; Tend: 200. C |
Van Den Dool and Kratz RI, polar column, custom temperature program
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | FFAP | 1788. | Yasuhara, 1987 | 50. m/0.25 mm/0.25 μm, He; Program: 20C (5min) => 2C/min => 70C => 4C/min => 210C |
Normal alkane RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | DB-1 | 764. | Chen, Wang, et al., 1998 | 60. m/0.32 mm/1. μm, He, 3. K/min; Tstart: 40. C; Tend: 260. C |
Normal alkane RI, polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | RTX-Wax | 1738. | Prososki, Etzel, et al., 2007 | 30. m/0.25 mm/0.5 μm, He, 40. C @ 5. min, 10. K/min, 220. C @ 10. min |
| Capillary | DB-Wax | 1764. | Wong and Bernhard, 1988 | He, 70. C @ 8. min, 2. K/min; Column length: 30. m; Column diameter: 0.25 mm; Tend: 160. C |
Normal alkane RI, polar column, custom temperature program
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | DB-Wax | 1763. | Kim. J.H., Ahn, et al., 2004 | 60. m/0.25 mm/0.25 μm, Helium; Program: 60 0C (3 min) 2 0C/min -> 150 0C 4 0C/min -> 200 0C |
| Capillary | DB-Wax | 1725. | Peng, Yang, et al., 1991 | Program: not specified |
| Capillary | DB-Wax | 1775. | Peng, Yang, et al., 1991 | Program: not specified |
References
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas Chromatography, 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]
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]
de Lacy Costello, Evans, et al., 2001
de Lacy Costello, B.P.J.; Evans, P.; Ewen, R.J.; Gunson, H.E.; Jones, P.R.H.; Ratcliffe, N.M.; Spencer-Phillips, P.T.N.,
Gas chromatography-mass spectrometry analyses of volatile organic compounds from potato tubers inoculated with Phytophthora infestans or Fusarium coeruleum,
Plant Pathol., 2001, 50, 4, 489-496, https://doi.org/10.1046/j.1365-3059.2001.00594.x
. [all data]
Yasuhara, 1987
Yasuhara, A.,
Identification of Volatile Compounds in Poultry Manure by Gas Chromatography-Mass Spectrometry,
J. Chromatogr., 1987, 387, 371-378, https://doi.org/10.1016/S0021-9673(01)94539-X
. [all data]
Chen, Wang, et al., 1998
Chen, J.; Wang, M.; Ho, C.-T.,
Volatile compounds generated from thermal degradation of N-acetylglucosamine,
J. Agric. Food Chem., 1998, 46, 8, 3207-3209, https://doi.org/10.1021/jf980129g
. [all data]
Prososki, Etzel, et al., 2007
Prososki, R.A.; Etzel, M.R.; Rankin, S.A.,
Solvent type affects the number, distribution, and relative quantities of volatile compounds found in sweet whey powder,
J. Dairy Sci., 2007, 90, 2, 523-531, https://doi.org/10.3168/jds.S0022-0302(07)71535-7
. [all data]
Wong and Bernhard, 1988
Wong, J.M.; Bernhard, R.A.,
Effect of nitrogen source on pyrazine formation,
J. Agric. Food Chem., 1988, 36, 1, 123-129, https://doi.org/10.1021/jf00079a032
. [all data]
Kim. J.H., Ahn, et al., 2004
Kim. J.H.; Ahn, H.J.; Yook, H.S.; Kim, K.S.; Rhee, M.S.; Ryu, G.H.; Byun, M.W.,
Color, flavor, and sensory characteristics of gamma-irradiated salted and fermented anchovy sauce,
Radiation Phys. Chem., 2004, 69, 2, 179-187, https://doi.org/10.1016/S0969-806X(03)00400-6
. [all data]
Peng, Yang, et al., 1991
Peng, C.T.; Yang, Z.C.; Ding, S.F.,
Prediction of rentention idexes. II. Structure-retention index relationship on polar columns,
J. Chromatogr., 1991, 586, 1, 85-112, https://doi.org/10.1016/0021-9673(91)80028-F
. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas Chromatography, References
- Symbols used in this document:
ΔfH°gas Enthalpy of formation of gas 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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