Acetophenone, 3'-chloro-
- Formula: C8H7ClO
- Molecular weight: 154.594
- IUPAC Standard InChIKey: UUWJBXKHMMQDED-UHFFFAOYSA-N
- CAS Registry Number: 99-02-5
- Chemical structure:
This structure is also available as a 2d Mol file - Other names: Ethanone, 1-(3-chlorophenyl)-; m-Chloroacetophenone; 3'-Chloroacetophenone; 3'-Chloroacetylphenone; 1-(3-Chlorophenyl)ethanone
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Phase change data
Go To: Top, Reaction thermochemistry 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: Robert L. Brown and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 501.2 | K | N/A | Aldrich Chemical Company Inc., 1990 |
Reaction thermochemistry 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 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
C8H6ClO- + =
By formula: C8H6ClO- + H+ = C8H7ClO
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 357.2 ± 2.1 | kcal/mol | G+TS | Bartmess, Scott, et al., 1979 | gas phase; value altered from reference due to change in acidity scale |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 350.4 ± 2.0 | kcal/mol | IMRE | Bartmess, Scott, et al., 1979 | gas phase; value altered from reference due to change in acidity scale |
Gas phase ion energetics 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 evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias
Data compiled as indicated in comments:
B - John E. Bartmess
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Proton affinity (review) | 202.4 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 194.8 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Electron affinity determinations
EA (eV) | Method | Reference | Comment |
---|---|---|---|
0.616 ± 0.087 | IMRE | Mishima, Huh, et al., 1995 | ΔGea(343 K) = -14.5 kcal/mol. Reanchored to EA(PhNO2), Kebarle and Chowdhury, 1987.; B |
0.585 ± 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 |
0.5832 ± 0.0056 | ECD | Steelhammer and Wentworth, 1969 | B |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
9.5 ± 0.1 | EI | Chin and Harrison, 1969 | RDSH |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C7H4OCl+ | 10.4 ± 0.1 | CH3 | EI | Chin and Harrison, 1969 | RDSH |
De-protonation reactions
C8H6ClO- + =
By formula: C8H6ClO- + H+ = C8H7ClO
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 357.2 ± 2.1 | kcal/mol | G+TS | Bartmess, Scott, et al., 1979 | gas phase; value altered from reference due to change in acidity scale; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 350.4 ± 2.0 | kcal/mol | IMRE | Bartmess, Scott, et al., 1979 | gas phase; value altered from reference due to change in acidity scale; B |
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
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-6407 |
NIST MS number | 229199 |
References
Go To: Top, Phase change data, Reaction thermochemistry 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.
Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc.,
Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [all data]
Bartmess, Scott, et al., 1979
Bartmess, J.E.; Scott, J.A.; McIver, R.T., Jr.,
The gas phase acidity scale from methanol to phenol,
J. Am. Chem. Soc., 1979, 101, 6047. [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]
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, Phase change data, Reaction thermochemistry 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 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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