Ethanone, 1-(4-chlorophenyl)-
- Formula: C8H7ClO
- Molecular weight: 154.594
- IUPAC Standard InChIKey: BUZYGTVTZYSBCU-UHFFFAOYSA-N
- CAS Registry Number: 99-91-2
- 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'-chloro-; p-Chloroacetophenone; 1-(4-Chlorophenyl)ethanone; 4'-Chloroacetophenone; 4-Chloroacetophenone; USAF do-1
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Phase change data
Go To: Top, 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 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 | 505.2 | K | N/A | Weast and Grasselli, 1989 | BS |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 291.55 | K | N/A | Dreisbach and Martin, 1949 | Uncertainty assigned by TRC = 0.05 K; TRC |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
54.0 | 419. | A | Stephenson and Malanowski, 1987 | Based on data from 404. to 623. K. See also Dykyj, Svoboda, et al., 1999.; AC |
50.7 | 410. | N/A | Dreisbach and Shrader, 1949 | Based on data from 395. to 485. K. See also Dreisbach and Martin, 1949, 2 and Boublik, Fried, et al., 1984.; AC |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (bar)
T = temperature (K)
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Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
395.16 to 485.09 | 4.24874 | 1722.075 | -79.206 | Dreisbach and Shrader, 1949 | Coefficents calculated by NIST from author's data. |
Gas phase ion energetics data
Go To: Top, 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
B - John E. Bartmess
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Proton affinity (review) | 856.6 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 824.8 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Electron affinity determinations
EA (eV) | Method | Reference | Comment |
---|---|---|---|
0.585 ± 0.087 | IMRE | Mishima, Huh, et al., 1995 | ΔGea(343 K) = -13.8 kcal/mol. Reanchored to EA(PhNO2), Kebarle and Chowdhury, 1987.; B |
0.551 ± 0.087 | IMRE | Huh, Kang, et al., 1999 | ΔG(EA) 343K; anchored to ΔG value. Including anchor ΔS, EA is ca. 0.4 kcal/mol more bound.; B |
0.5668 ± 0.0052 | ECD | Steelhammer and Wentworth, 1969 | B |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
9.63 | EI | Howe and Williams, 1969 | RDSH |
9.6 ± 0.1 | EI | Chin and Harrison, 1969 | RDSH |
9.47 ± 0.05 | EI | Foffani, Pignataro, et al., 1964 | RDSH |
9.64 ± 0.15 | EI | Buchs, Rossetti, et al., 1964 | RDSH |
9.25 | PE | Gal, Geribaldi, et al., 1985 | Vertical value; LBLHLM |
9.52 | PE | Pfister-Guillouzo, Geribaldi, et al., 1982 | Vertical value; LBLHLM |
9.60 ± 0.05 | PE | McAlduff, 1980 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C7H4OCl+ | 10.34 ± 0.03 | CH3 | EI | Helal and Zahran, 1978 | LLK |
C7H4OCl+ | 10.69 | CH3 | EI | Howe and Williams, 1969 | RDSH |
C7H4OCl+ | 10.4 ± 0.1 | CH3 | EI | Chin and Harrison, 1969 | RDSH |
C7H4OCl+ | 10.04 | CH3 | EI | Buchs, Rossetti, et al., 1964 | RDSH |
Mass spectrum (electron ionization)
Go To: Top, Phase change 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: NIST Mass Spectrometry Data Center, William E. Wallace, director
Spectrum
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Additional Data
View image of digitized spectrum (can be printed in landscape orientation).
Due to licensing restrictions, this spectrum cannot be downloaded.
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 | Japan AIST/NIMC Database- Spectrum MS-NW-3158 |
NIST MS number | 229194 |
References
Go To: Top, 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.
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]
Dreisbach and Martin, 1949
Dreisbach, R.R.; Martin, R.A.,
Physical Data on Some Organic Compounds,
Ind. Eng. Chem., 1949, 41, 2875-8. [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]
Dykyj, Svoboda, et al., 1999
Dykyj, J.; Svoboda, J.; Wilhoit, R.C.; Frenkel, M.L.; Hall, K.R.,
Vapor Pressure of Chemicals: Part A. Vapor Pressure and Antoine Constants for Hydrocarbons and Sulfur, Selenium, Tellurium and Hydrogen Containing Organic Compounds, Springer, Berlin, 1999, 373. [all data]
Dreisbach and Shrader, 1949
Dreisbach, R.R.; Shrader, S.A.,
Vapor Pressure--Temperature Data on Some Organic Compounds,
Ind. Eng. Chem., 1949, 41, 12, 2879-2880, https://doi.org/10.1021/ie50480a054
. [all data]
Dreisbach and Martin, 1949, 2
Dreisbach, R.R.; Martin, R.A.,
Physical Data on Some Organic Compounds,
Ind. Eng. Chem., 1949, 41, 12, 2875-2878, https://doi.org/10.1021/ie50480a053
. [all data]
Boublik, Fried, et al., 1984
Boublik, T.; Fried, V.; Hala, E.,
The Vapour Pressures of Pure Substances: Selected Values of the Temperature Dependence of the Vapour Pressures of Some Pure Substances in the Normal and Low Pressure Region, 2nd ed., Elsevier, New York, 1984, 972. [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]
Mishima, Huh, et al., 1995
Mishima, M.; Huh, C.; Lee, H.W.; Nakamura, H.; Fujio, M.; Tsuno, Y.,
Electron affinities of acetophenones and methyl benzoates. Varying resonance demand of aromatic radical anions,
Tetrahed. Lett., 1995, 36, 13, 2265, https://doi.org/10.1016/0040-4039(95)00267-G
. [all data]
Kebarle and Chowdhury, 1987
Kebarle, P.; Chowdhury, S.,
Electron affinities and electron transfer reactions,
Chem. Rev., 1987, 87, 513. [all data]
Huh, Kang, et al., 1999
Huh, C.; Kang, C.H.; Lee, H.W.; Nakamura, H.; Mishima, M.; Tsuno, Y.; Yamataka, H.,
Thermodynamic stabilities and resonance demand of aromatic radical anions in the gas phase,
Bull. Chem. Soc. Japan, 1999, 72, 5, 1083-1091, https://doi.org/10.1246/bcsj.72.1083
. [all data]
Steelhammer and Wentworth, 1969
Steelhammer, J.C.; Wentworth, W.E.,
Correlation of Electron Beam and Thermal Electron Attachment Studies for Some Chloro, Bromo, Iodo Aromatic Compounds,
J. Chem. Phys., 1969, 51, 5, 1802, https://doi.org/10.1063/1.1672262
. [all data]
Howe and Williams, 1969
Howe, I.; Williams, D.H.,
Calculation and qualitative predictions of mass spectra. Mono- and paradisubstituted benzenes,
J. Am. Chem. Soc., 1969, 91, 7137. [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]
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]
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]
Pfister-Guillouzo, Geribaldi, et al., 1982
Pfister-Guillouzo, G.; Geribaldi, S.; Gal, J.-F.,
Spectres photoelectroniques de cyclohexene-2-ones-1 diversement substituees en position 3. Correlations avec la reactivite,
Can. J. Chem., 1982, 60, 1163. [all data]
McAlduff, 1980
McAlduff, E.J.,
Photoelectron spectra of substituted acetophenones. Correlations with reactivity,
Can. J. Chem., 1980, 58, 622. [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]
Notes
Go To: Top, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), References
- Symbols used in this document:
AE Appearance energy EA Electron affinity Tboil Boiling point Tfus Fusion (melting) point ΔvapH Enthalpy of vaporization - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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