PhCðC anion
- Formula: C8H5-
- Molecular weight: 101.1258
- CAS Registry Number: 20404-08-4
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Reaction thermochemistry data
Go To: Top, 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:
B - John E. Bartmess
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
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Individual Reactions
By formula: C8H5- + CH4O = (C8H5- • CH4O)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 21.5 ± 2.0 | kcal/mol | IMRE | Chabinyc and Brauman, 1999 | gas phase; B |
ΔrH° | 21.4 ± 2.9 | kcal/mol | N/A | Caldwell, Rozeboom, et al., 1984 | gas phase; Reanchored to average data from Paul and Kebarle, 1990 and Meot-ner and Sieck, 1986.; value altered from reference due to change in acidity scale; B,M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 29.3 | cal/mol*K | N/A | Caldwell, Rozeboom, et al., 1984 | gas phase; switching reaction(CH3O-)CH3OH, Entropy change calculated or estimated; re-evaluated using Meot-Ner(Mautner), 1986 and Paul and Kebarle, 1990; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 11.0 ± 2.0 | kcal/mol | IMRE | Chabinyc and Brauman, 1999 | gas phase; B |
ΔrG° | 12.7 ± 2.0 | kcal/mol | IMRE | Caldwell, Rozeboom, et al., 1984 | gas phase; Reanchored to average data from Paul and Kebarle, 1990 and Meot-ner and Sieck, 1986.; value altered from reference due to change in acidity scale; B,M |
By formula: C8H5- + C7H8O = (C8H5- • C7H8O)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 26.6 ± 2.9 | kcal/mol | N/A | Caldwell, Rozeboom, et al., 1984 | gas phase; Reanchored to average data from Paul and Kebarle, 1990 and Meot-ner and Sieck, 1986.; value altered from reference due to change in acidity scale; B,M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 29.3 | cal/mol*K | N/A | Caldwell, Rozeboom, et al., 1984 | gas phase; switching reaction(CH3O-)CH3OH, Entropy change calculated or estimated; re-evaluated using Meot-Ner(Mautner), 1986 and Paul and Kebarle, 1990; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 17.9 ± 2.0 | kcal/mol | IMRE | Caldwell, Rozeboom, et al., 1984 | gas phase; Reanchored to average data from Paul and Kebarle, 1990 and Meot-ner and Sieck, 1986.; value altered from reference due to change in acidity scale; B,M |
By formula: C8H5- + C3H8O = (C8H5- • C3H8O)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 22.5 ± 2.9 | kcal/mol | N/A | Caldwell, Rozeboom, et al., 1984 | gas phase; Reanchored to average data from Paul and Kebarle, 1990 and Meot-ner and Sieck, 1986.; value altered from reference due to change in acidity scale; B,M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 29.3 | cal/mol*K | N/A | Caldwell, Rozeboom, et al., 1984 | gas phase; switching reaction(CH3O-)CH3OH, Entropy change calculated or estimated; re-evaluated using Meot-Ner(Mautner), 1986 and Paul and Kebarle, 1990; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 13.8 ± 2.0 | kcal/mol | IMRE | Caldwell, Rozeboom, et al., 1984 | gas phase; Reanchored to average data from Paul and Kebarle, 1990 and Meot-ner and Sieck, 1986.; value altered from reference due to change in acidity scale; B,M |
By formula: C8H5- + C5H12O = (C8H5- • C5H12O)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 24.2 ± 2.9 | kcal/mol | N/A | Caldwell, Rozeboom, et al., 1984 | gas phase; Reanchored to average data from Paul and Kebarle, 1990 and Meot-ner and Sieck, 1986.; value altered from reference due to change in acidity scale; B,M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 29.3 | cal/mol*K | N/A | Caldwell, Rozeboom, et al., 1984 | gas phase; switching reaction(CH3O-)CH3OH, Entropy change calculated or estimated; re-evaluated using Meot-Ner(Mautner), 1986 and Paul and Kebarle, 1990; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 15.5 ± 2.0 | kcal/mol | IMRE | Caldwell, Rozeboom, et al., 1984 | gas phase; Reanchored to average data from Paul and Kebarle, 1990 and Meot-ner and Sieck, 1986.; value altered from reference due to change in acidity scale; B,M |
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 370.6 ± 2.3 | 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° | 362.9 ± 2.0 | kcal/mol | IMRE | Bartmess, Scott, et al., 1979 | gas phase; value altered from reference due to change in acidity scale; B |
C8H5- + = C9H6F3-
By formula: C8H5- + CHF3 = C9H6F3-
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 19.3 ± 1.0 | kcal/mol | IMRE | Chabinyc and Brauman, 2000 | gas phase; Original dG=8.8 at 350K; dS based on symmetry alone; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 10.4 ± 1.0 | kcal/mol | IMRE | Chabinyc and Brauman, 2000 | gas phase; Original dG=8.8 at 350K; dS based on symmetry alone; B |
References
Go To: Top, Reaction thermochemistry data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Chabinyc and Brauman, 1999
Chabinyc, M.L.; Brauman, J.I.,
Hydrogen bond strength and acidity. Structural and energetic correlations for acetylides and alcohols,
J. Phys. Chem. A, 1999, 103, 46, 9163-9166, https://doi.org/10.1021/jp992852v
. [all data]
Caldwell, Rozeboom, et al., 1984
Caldwell, G.; Rozeboom, M.D.; Kiplinger, J.P.; Bartmess, J.E.,
Anion-alcohol hydrogen bond strengths in the gas phase,
J. Am. Chem. Soc., 1984, 106, 4660. [all data]
Paul and Kebarle, 1990
Paul, G.J.C.; Kebarle, P.,
Thermodynamics of the Association Reactions OH- - H2O = HOHOH- and CH3O- - CH3OH = CH3OHOCH3- in the Gas Phase,
J. Phys. Chem., 1990, 94, 12, 5184, https://doi.org/10.1021/j100375a076
. [all data]
Meot-ner and Sieck, 1986
Meot-ner, M.; Sieck, L.W.,
Relative acidities of water and methanol, and the stabilities of the dimer adducts,
J. Phys. Chem., 1986, 90, 6687. [all data]
Meot-Ner(Mautner), 1986
Meot-Ner(Mautner), M.,
Comparative Stabilities of Cationic and Anionic Hydrogen-Bonded Networks. Mixed Clusters of Water-Methanol,
J. Am. Chem. Soc., 1986, 108, 20, 6189, https://doi.org/10.1021/ja00280a014
. [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]
Chabinyc and Brauman, 2000
Chabinyc, M.L.; Brauman, J.I.,
Unusual ionic hydrogen bonds: Complexes of acetylides and fluoroform,
J. Am. Chem. Soc., 2000, 122, 36, 8739-8745, https://doi.org/10.1021/ja000806z
. [all data]
Notes
Go To: Top, Reaction thermochemistry data, References
- Symbols used in this document:
ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔrS° Entropy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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