Acetamide, N-phenyl-
- Formula: C8H9NO
- Molecular weight: 135.1632
- 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
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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:
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 | -209.5 ± 1.5 | kJ/mol | Ccr | Sato-Toshima, Kamagughi, et al., 1983 | Author was aware that data differs from previously reported values; ALS |
ΔfH°solid | -209.4 ± 1.0 | kJ/mol | Ccb | Johnson, 1975 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°solid | -4224.8 ± 1.0 | kJ/mol | Ccr | Sato-Toshima, Kamagughi, et al., 1983 | Author was aware that data differs from previously reported values; ALS |
ΔcH°solid | -4224.88 ± 0.93 | kJ/mol | Ccb | Johnson, 1975 | ALS |
Constant pressure heat capacity of solid
Cp,solid (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
179.3 | 298.15 | Nilsson and Wadso, 1986 | DH |
191.6 | 323. | Satoh and Sogabe, 1941 | T = 0 to 100 C. Mean value.; DH |
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
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° | 1454. ± 8.8 | kJ/mol | G+TS | Taft and Bordwell, 1988 | gas phase; B |
ΔrH° | 1476. ± 9.6 | kJ/mol | G+TS | Cumming and Kebarle, 1978 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1425. ± 8.4 | kJ/mol | IMRE | Taft and Bordwell, 1988 | gas phase; B |
ΔrG° | 1447. ± 8.4 | kJ/mol | IMRE | Cumming and Kebarle, 1978 | gas phase; B |
+
= C10H11NO2 +
By formula: C8H9NO + C2H4O2 = C10H11NO2 + H2O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 45.5 ± 0.3 | kJ/mol | Cm | Wadso, 1965 | solid phase; Heat of hydrolysis; ALS |
By formula: C8H9NO + H2O = C6H7N + C2H4O2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -42.0 ± 0.3 | kJ/mol | Cm | Wadso, 1965 | solid phase; Heat of hydrolysis; ALS |
By formula: C4H5N3O + C6H7N = C8H9NO + C2H3N3
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -72.3 ± 0.3 | kJ/mol | Cm | Wadso, 1962 | solid phase; ALS |
By formula: C3H4N4O + C6H7N = C8H9NO + CH2N4
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -84.6 ± 0.3 | kJ/mol | Cm | Wadso, 1962 | solid phase; ALS |
By formula: C4H6O3 + C6H7N = C8H9NO + C2H4O2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -100.9 ± 0.3 | kJ/mol | Cm | Wadso, 1962 | liquid phase; ALS |
Gas phase ion energetics data
Go To: Top, Condensed 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:
B - John E. Bartmess
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
8.30 ± 0.10 | PE | Bouchoux, 1978 | LLK |
8.60 | EI | Baldwin, Loudon, et al., 1976 | LLK |
8.18 ± 0.03 | EI | Benezra and Bursey, 1971 | LLK |
8.39 ± 0.10 | EI | Cotter, 1964 | RDSH |
8.46 | PE | Nakagaki, Kobayashi, et al., 1980 | Vertical value; LLK |
8.46 ± 0.05 | PE | Szepes, Distefano, et al., 1974 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C2H3O+ | 13.22 ± 0.03 | ? | EI | Benezra and Bursey, 1971 | LLK |
C6H7N+ | 10.60 | ? | EI | Baldwin, Loudon, et al., 1976 | LLK |
C6H7N+ | 10.45 ± 0.03 | CH2=C=O | EI | Benezra and Bursey, 1971 | LLK |
C6H7N+ | 8.88 ± 0.15 | ? | EI | Cotter, 1964 | RDSH |
C8H8NO+ | 11.00 | H | EI | Baldwin, Loudon, et al., 1976 | LLK |
De-protonation reactions
C8H8NO- + =
By formula: C8H8NO- + H+ = C8H9NO
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1454. ± 8.8 | kJ/mol | G+TS | Taft and Bordwell, 1988 | gas phase; B |
ΔrH° | 1476. ± 9.6 | kJ/mol | G+TS | Cumming and Kebarle, 1978 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1425. ± 8.4 | kJ/mol | IMRE | Taft and Bordwell, 1988 | gas phase; B |
ΔrG° | 1447. ± 8.4 | kJ/mol | IMRE | Cumming and Kebarle, 1978 | gas phase; B |
References
Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics 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]
Bouchoux, 1978
Bouchoux, G.,
Ionisation et fragmentation en spectrometrie de masse VIII. Energies d'activation de deux fragmentations competitives, dissociation de l'acetate de phenyle et de l'acetanilide sous impact electronique,
Int. J. Mass Spectrom. Ion Phys., 1978, 26, 379. [all data]
Baldwin, Loudon, et al., 1976
Baldwin, M.A.; Loudon, A.G.; Maccoll, A.; Webb, K.S.,
The nature and fragmentation pathways of the molecular ions of some arylureas, arylthioureas, acetanilides, thioacetanilides and related compounds,
Org. Mass Spectrom., 1976, 11, 1181. [all data]
Benezra and Bursey, 1971
Benezra, S.A.; Bursey, M.M.,
ortho-Effects on ordering factors in mass spectral rearrangements. Loss of keten from halogenated phenyl acetates and acetanilides,
J. Chem. Soc. B, 1971, 1515. [all data]
Cotter, 1964
Cotter, J.L.,
Electron impact fragmentation patterns of acetanilide and benzamide,
J. Chem. Soc., 1964, 5477. [all data]
Nakagaki, Kobayashi, et al., 1980
Nakagaki, R.; Kobayashi, T.; Nagakura, S.,
Conformations of acetanilide and related compounds studied by ultraviolet photoelectron spectroscopy,
Bull. Chem. Soc. Jpn., 1980, 53, 901. [all data]
Szepes, Distefano, et al., 1974
Szepes, L.; Distefano, G.; Pignataro, S.,
Steric inhibition of resonance in acetanilides by UV photoelectron spectroscopy,
Ann. Chim., 1974, 64, 159. [all data]
Notes
Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance energy 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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