Acetamide, N-phenyl-
- Formula: C8H9NO
- Molecular weight: 135.1632
- IUPAC Standard InChI: InChI=1S/C8H9NO/c1-7(10)9-8-5-3-2-4-6-8/h2-6H,1H3,(H,9,10)
- IUPAC Standard InChIKey: FZERHIULMFGESH-UHFFFAOYSA-N
- CAS Registry Number: 103-84-4
- 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: Acetanilide; Acetamidobenzene; Acetanil; Acetoanilide; Acetylaniline; Antifebrin; Benzenamine, N-acetyl-; N-Acetylaniline; N-Phenylacetamide; Phenalgene; Phenalgin; Acetylaminobenzene; Acetic acid anilide; Acetanilid; Aniline, N-acetyl-; USAF EK-3; AN [Analgesic]; N-Acetylaminobenzene; NSC 7636
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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 |
|---|---|---|---|---|---|
| ΔfH°solid | -50.07 ± 0.36 | kcal/mol | Ccr | Sato-Toshima, Kamagughi, et al., 1983 | Author was aware that data differs from previously reported values; ALS |
| ΔfH°solid | -50.06 ± 0.24 | kcal/mol | Ccb | Johnson, 1975 | ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°solid | -1009.8 ± 0.24 | kcal/mol | Ccr | Sato-Toshima, Kamagughi, et al., 1983 | Author was aware that data differs from previously reported values; ALS |
| ΔcH°solid | -1009.77 ± 0.22 | kcal/mol | Ccb | Johnson, 1975 | ALS |
Constant pressure heat capacity of solid
| Cp,solid (cal/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 42.85 | 298.15 | Nilsson and Wadso, 1986 | DH |
| 45.79 | 323. | Satoh and Sogabe, 1941 | T = 0 to 100 C. Mean value.; 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 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
C8H8NO- + =
By formula: C8H8NO- + H+ = C8H9NO
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 347.5 ± 2.1 | kcal/mol | G+TS | Taft and Bordwell, 1988 | gas phase; B |
| ΔrH° | 352.8 ± 2.3 | kcal/mol | G+TS | Cumming and Kebarle, 1978 | gas phase; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 340.6 ± 2.0 | kcal/mol | IMRE | Taft and Bordwell, 1988 | gas phase; B |
| ΔrG° | 345.8 ± 2.0 | kcal/mol | IMRE | Cumming and Kebarle, 1978 | gas phase; B |
+
= C10H11NO2 +
By formula: C8H9NO + C2H4O2 = C10H11NO2 + H2O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 10.88 ± 0.07 | kcal/mol | Cm | Wadso, 1965 | solid phase; Heat of hydrolysis; ALS |
+
=
+
By formula: C8H9NO + H2O = C6H7N + C2H4O2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -10.05 ± 0.06 | kcal/mol | Cm | Wadso, 1965 | solid phase; Heat of hydrolysis; ALS |
+
=
+
By formula: C4H5N3O + C6H7N = C8H9NO + C2H3N3
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -17.28 ± 0.08 | kcal/mol | Cm | Wadso, 1962 | solid phase; ALS |
+
=
+
By formula: C3H4N4O + C6H7N = C8H9NO + CH2N4
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -20.22 ± 0.08 | kcal/mol | Cm | Wadso, 1962 | solid phase; ALS |
+
=
+
By formula: C4H6O3 + C6H7N = C8H9NO + C2H4O2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -24.11 ± 0.06 | kcal/mol | Cm | Wadso, 1962 | liquid phase; ALS |
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.
Sato-Toshima, Kamagughi, et al., 1983
Sato-Toshima, T.; Kamagughi, A.; Nishiyama, K.; Sakiyama, M.; Seki, S.,
Enthalpies of combustion of organic compounds. IV. Acetaneilide and nicotinic acid,
Bull. Chem. Soc. Jpn., 1983, 56, 51-54. [all data]
Johnson, 1975
Johnson, W.H.,
The enthalpies of combustion and formation of acetanilide and urea,
J. Res. NBS, 1975, 79, 487-491. [all data]
Nilsson and Wadso, 1986
Nilsson, S.-O.; Wadso, I.,
A flow-microcalorimetric vessel for solution of slightly soluble solids,
J. Chem. Thermodynam., 1986, 18, 1125-1133. [all data]
Satoh and Sogabe, 1941
Satoh, S.; Sogabe, T.,
The heat capacities of some organic compounds containing nitrogen and the atomic heat of nitrogen. (1), Sci.,
Pap. Inst. Phys. Chem. Res. (Tokyo), 1941, 38, 197-203. [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]
Cumming and Kebarle, 1978
Cumming, J.B.; Kebarle, P.,
Summary of gas phase measurements involving acids AH. Entropy changes in proton transfer reactions involving negative ions. Bond dissociation energies D(A-H) and electron affinities EA(A),
Can. J. Chem., 1978, 56, 1. [all data]
Wadso, 1965
Wadso, I.,
Thermochemical properties of diacetimide, N-butyldiacetimide and N-phenyldiacetimide,
Acta Chem. Scand., 1965, 19, 1079-1087. [all data]
Wadso, 1962
Wadso, I.,
Heats of aminolysis and hydrolysis of some N-acetyl compounds and of acetic anhydride,
Acta Chem. Scand., 1962, 16, 471-478. [all data]
Notes
Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, References
- Symbols used in this document:
Cp,solid Constant pressure heat capacity of solid ΔcH°solid Enthalpy of combustion of solid 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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