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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Phase change data
Go To: Top, 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 as indicated in comments:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 567.2 | K | N/A | Weast and Grasselli, 1989 | BS |
Tboil | 566. to 568. | K | N/A | Buckingham and Donaghy, 1982 | BS |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 379. | K | N/A | Buckingham and Donaghy, 1982 | BS |
Tfus | 379.15 | K | N/A | Curran and Estok, 1950 | Uncertainty assigned by TRC = 1. K; TRC |
Enthalpy of sublimation
ΔsubH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
92.7 | 326. | A | Stephenson and Malanowski, 1987 | Based on data from 314. to 338. K. See also Aihara, 1960.; AC |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
19.6 | 378.2 | DSC | Chen, Tang, et al., 2005 | AC |
Gas phase ion energetics data
Go To: Top, Phase change 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) | 908.8 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 877.0 | kJ/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° | 1470. ± 8.8 | kJ/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° | 1439. ± 8.4 | kJ/mol | IMRE | Taft and Topsom, 1987 | gas phase; value altered from reference due to change in acidity scale; B |
References
Go To: Top, Phase change 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.
Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [all data]
Buckingham and Donaghy, 1982
Buckingham, J.; Donaghy, S.M.,
Dictionary of Organic Compounds: Fifth Edition, Chapman and Hall, New York, 1982, 1. [all data]
Curran and Estok, 1950
Curran, B.C.; Estok, G.K.,
The Stabilization of Highly Polar Resonacne Structures by Hydrogen Bonding I. Electric Moments,
J. Am. Chem. Soc., 1950, 72, 4575. [all data]
Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw,
Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2
. [all data]
Aihara, 1960
Aihara, Ariyuki,
Estimation of the Energy of Hydrogen Bonds Formed in Crystals. III. Amides,
Bull. Chem. Soc. Jpn., 1960, 33, 9, 1188-1194, https://doi.org/10.1246/bcsj.33.1188
. [all data]
Chen, Tang, et al., 2005
Chen, Yan-Ping; Tang, Muoi; Kuo, Ju-Chia,
Solid--liquid equilibria for binary mixtures of N-phenylacetamide with 4-aminoacetophenone, 3-hydroxyacetophenone and 4-hydroxyacetophenone,
Fluid Phase Equilibria, 2005, 232, 1-2, 182-188, https://doi.org/10.1016/j.fluid.2005.03.023
. [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]
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]
Notes
Go To: Top, Phase change data, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance energy Tboil Boiling point Tfus Fusion (melting) point ΔfusH Enthalpy of fusion ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔsubH Enthalpy of sublimation - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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