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
- Permanent link for this species. Use this link for bookmarking this species for future reference.
- Information on this page:
- Other data available:
- Data at other public NIST sites:
- Options:
Data at NIST subscription sites:
NIST subscription sites provide data under the NIST Standard Reference Data Program, but require an annual fee to access. The purpose of the fee is to recover costs associated with the development of data collections included in such sites. Your institution may already be a subscriber. Follow the links above to find out more about the data in these sites and their terms of usage.
Gas phase ion energetics data
Go To: Top, 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, 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.
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]
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]
Notes
Go To: Top, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance energy 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
- The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment. However, NIST makes no warranties to that effect, and NIST shall not be liable for any damage that may result from errors or omissions in the Database.
- Customer support for NIST Standard Reference Data products.