Acetophenone, 4'-amino-
- Formula: C8H9NO
- Molecular weight: 135.1632
- IUPAC Standard InChIKey: GPRYKVSEZCQIHD-UHFFFAOYSA-N
- CAS Registry Number: 99-92-3
- 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: Ethanone, 1-(4-aminophenyl)-; p-Acetylaniline; p-Aminoacetophenone; p-Aminoacetylbenzene; 4-Acetylaniline; 4'-Aminoacetophenone; 1-(4-Aminophenyl)ethanone; 4-Aminoacetophenone; Acetophenone, p-amino-; p-Aminoacetofenonu; USAF EK-631; 1-Acetyl-4-aminobenzene; NSC 3242
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Condensed phase thermochemistry data
Go To: Top, Reaction thermochemistry data, Gas phase ion energetics 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: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°solid | -43.5 ± 0.1 | kcal/mol | Ccb | Lebedeva, Gutner, et al., 1971 | Hfusion=3.8±0.1, see Lebedeva, Rjadnenko, et al., 1969 |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°solid | -1016.3 ± 0.1 | kcal/mol | Ccb | Lebedeva, Gutner, et al., 1971 | Hfusion=3.8±0.1, see Lebedeva, Rjadnenko, et al., 1969 |
ΔcH°solid | -1129.7 ± 0.2 | kcal/mol | Ccb | Sullivan and Hunt, 1949 | |
ΔcH°solid | -1130.41 ± 0.20 | kcal/mol | Ccb | Sullivan, Kibler, et al., 1948 |
Reaction thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Gas phase ion energetics 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: John E. Bartmess
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° | 351.3 ± 2.1 | kcal/mol | G+TS | Taft and Topsom, 1987 | gas phase; value altered from reference due to change in acidity scale |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 344.0 ± 2.0 | kcal/mol | IMRE | Taft and Topsom, 1987 | gas phase; value altered from reference due to change in acidity scale |
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 evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias
Data compiled as indicated in comments:
B - John E. Bartmess
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Proton affinity (review) | 217.2 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 209.6 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
7.8 ± 0.1 | PE | Egdell, Green, et al., 1975 | LLK |
8.3 ± 0.1 | EI | Chin and Harrison, 1969 | RDSH |
8.17 ± 0.02 | EI | Foffani, Pignataro, et al., 1964 | RDSH |
8.27 | PE | Gal, Geribaldi, et al., 1985 | Vertical value; LBLHLM |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C7H6NO+ | 10.2 ± 0.2 | CH3 | EI | Chin and Harrison, 1969 | RDSH |
C7H6NO+ | 9.34 | CH3 | EI | Buchs, Rossetti, et al., 1964 | RDSH |
De-protonation reactions
C8H8NO- + =
By formula: C8H8NO- + H+ = C8H9NO
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 351.3 ± 2.1 | kcal/mol | G+TS | Taft and Topsom, 1987 | gas phase; value altered from reference due to change in acidity scale; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 344.0 ± 2.0 | kcal/mol | IMRE | Taft and Topsom, 1987 | gas phase; value altered from reference due to change in acidity scale; 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.
Lebedeva, Gutner, et al., 1971
Lebedeva, N.D.; Gutner, N.M.; Ryadnenko, V.L.,
Heats of combustion and formation of certain aromatic amino-derivatives,
Russ. J. Phys. Chem. (Engl. Transl.), 1971, 45, 561-562. [all data]
Lebedeva, Rjadnenko, et al., 1969
Lebedeva, N.D.; Rjadnenko, B.L.; Gutner, N.M.,
Heats of formation of some N-containing organic compounds,
Int. Conf. Calorim. Therm. (Warsaw, Poland), 1969, 1-8. [all data]
Sullivan and Hunt, 1949
Sullivan, M.V.; Hunt, H.,
Heats of combustion. IV. The heats of combustion of five aromatic amines,
J. Phys. Chem., 1949, 53, 497-500. [all data]
Sullivan, Kibler, et al., 1948
Sullivan, M.V.; Kibler, G.M.; Hunt, H.,
Heats of combustion of nitrogen containing compounds, Rpt. Tech. Memo. PUR-3 for USN Project SQUID Contract N6ori-104, Task Order No. 1 Designation No. NR 22 042 by Purdue University, Lafayette, IN, 1948, 1-46. [all data]
Taft and Topsom, 1987
Taft, R.W.; Topsom, R.D.,
The Nature and Analysis of Substituent Effects,
Prog. Phys. Org. Chem., 1987, 16, 1. [all data]
Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G.,
Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update,
J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018
. [all data]
Egdell, Green, et al., 1975
Egdell, R.; Green, J.C.; Rao, C.N.R.,
Photoelectron spectra of substituted benzenes,
Chem. Phys. Lett., 1975, 33, 600. [all data]
Chin and Harrison, 1969
Chin, M.S.; Harrison, A.G.,
Substituent effects on ion abundances and energetics in substituted acetophenones,
Org. Mass Spectrom., 1969, 2, 1073. [all data]
Foffani, Pignataro, et al., 1964
Foffani, A.; Pignataro, S.; Cantone, B.; Grasso, F.,
Ionization potentials and substituent effects for aromatic carbonyl compounds,
Z. Physik. Chem. (Frankfurt), 1964, 42, 221. [all data]
Gal, Geribaldi, et al., 1985
Gal, J.-F.; Geribaldi, S.; Pfister-Guillouzo, G.; Morris, D.G.,
Basicity of the carbonyl group. Part 12. Correlations between ionization potentials and lewis basicities in aromatic carbonyl compounds,
J. Chem. Soc. Perkin Trans. 2, 1985, 103. [all data]
Buchs, Rossetti, et al., 1964
Buchs, A.; Rossetti, G.P.; Susz, B.P.,
Etude, en fonction de la constante σp de Hammett, du spectre de masse d'acetophenones p-substituees,
Helv. Chim. Acta, 1964, 47, 1563. [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 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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