PhCðC anion
- Formula: C8H5-
- Molecular weight: 101.1258
- CAS Registry Number: 20404-08-4
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Reaction thermochemistry 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:
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 |
Gas phase ion energetics data
Go To: Top, Reaction thermochemistry 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: John E. Bartmess
Electron affinity of neutral species
EAneutral (eV) | Method | Reference | Comment |
---|---|---|---|
3.21 ± 0.20 | D-EA | Bartmess, Scott, et al., 1979 | value altered from reference due to change in acidity scale |
Protonation reactions
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 |
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 |
References
Go To: Top, Reaction thermochemistry 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.
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, Gas phase ion energetics data, References
- Symbols used in this document:
EAneutral Electron affinity of neutral species 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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