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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Reaction thermochemistry data
Go To: Top, IR Spectrum, Gas Chromatography, 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 |
IR Spectrum
Go To: Top, Reaction thermochemistry data, Gas Chromatography, References, Notes
Data compiled by: Coblentz Society, Inc.
- SOLID (KBr PELLET); Not specified, most likely a prism, grating, or hybrid spectrometer.; DIGITIZED BY NIST FROM HARD COPY; 4 cm-1 resolution
- SOLID (SPLIT MULL); PERKIN-ELMER 521 (GRATING); DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 2 cm-1 resolution
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Gas Chromatography
Go To: Top, Reaction thermochemistry data, IR Spectrum, 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
Normal alkane RI, non-polar column, custom temperature program
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | Polydimethyl siloxanes | 1362. | Zenkevich and Chupalov, 1996 | Program: not specified |
| Capillary | Polydimethyl siloxanes | 1362. | Schutz and Wollrab A., 1988 | Program: not specified |
| Other | Methyl Silicone | 1358. | Ardrey and Moffat, 1981 | Program: not specified |
References
Go To: Top, Reaction thermochemistry data, IR Spectrum, Gas Chromatography, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
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]
Zenkevich and Chupalov, 1996
Zenkevich, I.G.; Chupalov, A.A.,
New Possibilities of Chromato Mass Pectrometric Identification of Organic Compounds Using Increments of Gas Chromatographic Retention Indices of Molecular Structural Fragments,
Zh. Org. Khim. (Rus.), 1996, 32, 5, 656-666. [all data]
Schutz and Wollrab A., 1988
Schutz, H.; Wollrab A.,
The significance of the retention index in toxicologic analysis II,
Pharmazie in unzerer Zeit, 1988, 17, 4, 97-101. [all data]
Ardrey and Moffat, 1981
Ardrey, R.E.; Moffat, A.C.,
Gas-liquid chromatographic retention indices of 1318 substances of toxicological interest on SE-30 or OV-1 stationary phase,
J. Chromatogr., 1981, 220, 3, 195-252, https://doi.org/10.1016/S0021-9673(00)81925-1
. [all data]
Notes
Go To: Top, Reaction thermochemistry data, IR Spectrum, Gas Chromatography, References
- Symbols used in this document:
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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