4-Acetylanisole
- Formula: C9H10O2
- Molecular weight: 150.1745
- IUPAC Standard InChIKey: NTPLXRHDUXRPNE-UHFFFAOYSA-N
- CAS Registry Number: 100-06-1
- 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: Acetophenone, 4'-methoxy-; Ethanone, 1-(4-methoxyphenyl)-; p-Acetylanisole; p-Methoxyacetophenone; p-Methoxyphenyl methyl ketone; Linarodin; Novatone; Vananote; 4-Methoxyphenyl methyl ketone; 4'-Methoxyacetophenone; 4-Methoxyacetophenone; para-Methoxyacetophenone; Acetanisole; Methyl p-methoxyphenyl ketone; 4-Methoxyacetofenon; Acetophenone, p-methoxy-; p-Metoxyacetophenone; Methyl 4-methoxyphenyl ketone; NSC 209523; 4-Methoxyacetophenon; Anise ketone; 1-(4-Methoxyphenyl)ethanone; para-Methoxyacetophenone (acetanisole)
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Condensed phase thermochemistry data
Go To: Top, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), 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 |
---|---|---|---|---|---|
ΔcH°liquid | -1116.1 | kcal/mol | Ccb | Seno, Tsuchiya, et al., 1975 | Corresponding ΔfHºliquid = -71.9 kcal/mol (simple calculation by NIST; no Washburn corrections) |
Phase change 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:
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
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 531.2 | K | N/A | Weast and Grasselli, 1989 | BS |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 312. | K | N/A | Vowinkel, 1966 | Uncertainty assigned by TRC = 3. K; TRC |
Tfus | 311.65 | K | N/A | Serpinskii, Voitkevich, et al., 1958 | Uncertainty assigned by TRC = 1.5 K; TRC |
Tfus | 311.4 | K | N/A | Serpinskii, Voitkevich, et al., 1954 | Uncertainty assigned by TRC = 0.7 K; TRC |
Tfus | 311.15 | K | N/A | Atkins, 1915 | Uncertainty assigned by TRC = 1. K; TRC |
Reduced pressure boiling point
Tboil (K) | Pressure (atm) | Reference | Comment |
---|---|---|---|
426.2 | 0.034 | Aldrich Chemical Company Inc., 1990 | BS |
411.7 | 0.020 | Weast and Grasselli, 1989 | BS |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
15.9 | 322. | A,ME | Stephenson and Malanowski, 1987 | Based on data from 311. to 334. K. See also Serpinskii, Voitkevich, et al., 1954, 2.; AC |
Enthalpy of sublimation
ΔsubH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
18.56 ± 0.05 | 311.4 | V | Aihara, 1959 | crystal phase; ALS |
18.6 | 276. to 300. | V | Aihara, 1959, 2 | AC |
22.4 | 308. | A | Serpinskii, Voitkevich, et al., 1954, 2 | Based on data from 283. to 333. K. See also Jones, 1960 and Stephenson and Malanowski, 1987.; AC |
Gas phase ion energetics data
Go To: Top, Condensed phase thermochemistry data, Phase change data, Mass spectrum (electron ionization), 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:
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) | 214.1 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 206.4 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
8.2 ± 0.1 | PE | Egdell, Green, et al., 1975 | LLK |
8.62 ± 0.05 | EI | Foffani, Pignataro, et al., 1964 | RDSH |
8.52 | PE | Distefano, Granozzi, et al., 1987 | Vertical value; LBLHLM |
8.65 | PE | Gal, Geribaldi, et al., 1985 | Vertical value; LBLHLM |
8.65 | PE | Koenig, Wielesek, et al., 1977 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C8H7O2+ | 10.69 ± 0.04 | CH3 | EI | Helal and Zahran, 1978 | LLK |
C8H7O2+ | 10.2 ± 0.1 | CH3 | EI | Chin and Harrison, 1969 | RDSH |
Mass spectrum (electron ionization)
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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 by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Spectrum
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Additional Data
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Owner | NIST Mass Spectrometry Data Center Collection (C) 2014 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
---|---|
Origin | D.HENNEBERG, MAX-PLANCK INSTITUTE, MULHEIM, WEST GERMANY |
NIST MS number | 63846 |
References
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Seno, Tsuchiya, et al., 1975
Seno, M.; Tsuchiya, S.; Kise, H.; Asahara, T.,
Studies on bond character in phosphorus ylides by combustion heat and x-ray photoelectron spectroscopy,
Bull. Chem. Soc. Jpn., 1975, 48, 2001-2005. [all data]
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]
Vowinkel, 1966
Vowinkel, E.,
Preparation of Aryl Alky8 Ethers by Means of O-Alkyl-N,N'-dicyclohexyl- isoureas,
Chem. Ber., 1966, 99, 1479-84. [all data]
Serpinskii, Voitkevich, et al., 1958
Serpinskii, V.V.; Voitkevich, S.A.; Lyuboshits, N.Yu.,
Trudy Vsesoyuz. Nauch.-Issledovatel. Inst. Sintet. I. Natural. Dushistykh Veshchestv, 1958, 4, 125. [all data]
Serpinskii, Voitkevich, et al., 1954
Serpinskii, V.V.; Voitkevich, S.A.; Lyuboshits, N.Y.,
Zh. Fiz. Khim., 1954, 28, 1969. [all data]
Atkins, 1915
Atkins, W.R.G.,
Spectrochemical Experiments,
Justus Liebigs Ann. Chem., 1915, 408, 212. [all data]
Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc.,
Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [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]
Serpinskii, Voitkevich, et al., 1954, 2
Serpinskii, V.V.; Voitkevich, S.A.; Lyuboshits, N.Y.,
Zh. Fiz. Khim., 1954, 28, 810. [all data]
Aihara, 1959
Aihara, A.,
Estimation of the energy of hydrogen bonds formed in crystals. I. Sublimation pressures of some organic molecular crystals and the additivity of lattice energy,
Bull. Chem. Soc. Jpn., 1959, 32, 1242. [all data]
Aihara, 1959, 2
Aihara, Ariyuki,
Estimation of the Energy of Hydrogen Bonds Formed in Crystals. I. Sublimation Pressures of Some Organic Molecular Crystals and the Additivity of Lattice Energy,
Bull. Chem. Soc. Jpn., 1959, 32, 11, 1242-1248, https://doi.org/10.1246/bcsj.32.1242
. [all data]
Jones, 1960
Jones, A.H.,
Sublimation Pressure Data for Organic Compounds.,
J. Chem. Eng. Data, 1960, 5, 2, 196-200, https://doi.org/10.1021/je60006a019
. [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]
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]
Distefano, Granozzi, et al., 1987
Distefano, G.; Granozzi, G.; Olivato, P.R.; Guerrero, S.A.,
Hyperconjugative interactions in halogen-substituted carbonyls: Ultraviolet photoelectron spectroscopy of w-halogenoacetophenones,
J. Chem. Soc. Perkin Trans. 2, 1987, 1459. [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]
Koenig, Wielesek, et al., 1977
Koenig, T.; Wielesek, R.; Miller, L.L.; So, Y.-H.,
Correlation of electrochemical reactivity and photoelectron spectra of aromatic ketones,
J. Am. Chem. Soc., 1977, 99, 7061. [all data]
Helal and Zahran, 1978
Helal, A.I.; Zahran, N.F.,
Kinetic shift in some para-substituted acetophenones,
Org. Mass Spectrom., 1978, 13, 549. [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]
Notes
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), References
- Symbols used in this document:
AE Appearance energy Tboil Boiling point Tfus Fusion (melting) point ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔsubH Enthalpy of sublimation ΔvapH Enthalpy of vaporization - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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