thiophenoxide anion
- Formula: C6H5S-
- Molecular weight: 109.169
- IUPAC Standard InChI: InChI=1S/C6H6S/c7-6-4-2-1-3-5-6/h1-5,7H/p-1
- IUPAC Standard InChIKey: RMVRSNDYEFQCLF-UHFFFAOYSA-M
- CAS Registry Number: 13133-62-5
- Chemical structure:
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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
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
+
=
By formula: C6H5S- + H+ = C6H6S
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 340.4 ± 2.1 | kcal/mol | G+TS | Taft and Bordwell, 1988 | gas phase; B |
| ΔrH° | >340.1 ± 1.8 | kcal/mol | D-EA | Richardson, Stephenson, et al., 1975 | gas phase; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 333.4 ± 2.1 | kcal/mol | IMRE | Guillemin, Riague, et al., 2005 | gas phase; B |
| ΔrG° | 333.8 ± 2.0 | kcal/mol | IMRE | Taft and Bordwell, 1988 | gas phase; B |
| ΔrG° | >333.5 ± 1.9 | kcal/mol | H-TS | Richardson, Stephenson, et al., 1975 | gas phase; B |
+
= C6H7OS-
By formula: C6H5S- + H2O = C6H7OS-
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 11.40 ± 0.20 | kcal/mol | TDAs | Sieck and Meot-ner, 1989 | gas phase; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 5.60 ± 0.70 | kcal/mol | TDAs | Sieck and Meot-ner, 1989 | gas phase; B |
+
= C8H9O2S-
By formula: C6H5S- + C2H4O2 = C8H9O2S-
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 20.30 ± 0.10 | kcal/mol | TDAs | Sieck and Meot-ner, 1989 | gas phase; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 12.50 ± 0.40 | kcal/mol | TDAs | Sieck and Meot-ner, 1989 | gas phase; B |
+
= C8H8F3OS-
By formula: C6H5S- + C2H3F3O = C8H8F3OS-
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 21.00 ± 0.20 | kcal/mol | TDAs | Sieck and Meot-ner, 1989 | gas phase; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 13.50 ± 0.60 | kcal/mol | TDAs | Sieck and Meot-ner, 1989 | gas phase; B |
+
= C7H9OS-
By formula: C6H5S- + CH4O = C7H9OS-
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 13.40 ± 0.10 | kcal/mol | TDAs | Sieck and Meot-ner, 1989 | gas phase; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 6.50 ± 0.30 | kcal/mol | TDAs | Sieck and Meot-ner, 1989 | gas phase; B |
+
= C9H13OS-
By formula: C6H5S- + C3H8O = C9H13OS-
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 15.00 ± 0.10 | kcal/mol | TDAs | Sieck and Meot-ner, 1989 | gas phase; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 7.30 ± 0.40 | kcal/mol | TDAs | Sieck and Meot-ner, 1989 | gas phase; B |
+
= C10H15OS-
By formula: C6H5S- + C4H10O = C10H15OS-
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 14.60 ± 0.10 | kcal/mol | TDAs | Sieck and Meot-ner, 1989 | gas phase; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 7.20 ± 0.50 | kcal/mol | TDAs | Sieck and Meot-ner, 1989 | gas phase; B |
+
= C9H11O2S-
By formula: C6H5S- + C3H6O2 = C9H11O2S-
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 20.00 ± 0.40 | kcal/mol | TDAs | Sieck and Meot-ner, 1989 | gas phase; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 12.4 ± 1.3 | kcal/mol | TDAs | Sieck and Meot-ner, 1989 | gas phase; B |
+
= (
•
)
By formula: C6H5S- + H2O = (C6H5S- • H2O)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 11.4 | kcal/mol | PHPMS | Sieck and Meot-ner, 1989 | gas phase; M |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrS° | 19.6 | cal/mol*K | PHPMS | Sieck and Meot-ner, 1989 | gas phase; M |
+
= (
•
)
By formula: C6H5S- + C3H6O2 = (C6H5S- • C3H6O2)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 20.0 | kcal/mol | PHPMS | Sieck and Meot-ner, 1989 | gas phase; M |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrS° | 25.6 | cal/mol*K | PHPMS | Sieck and Meot-ner, 1989 | gas phase; M |
+
= (
•
)
By formula: C6H5S- + C2H4O2 = (C6H5S- • C2H4O2)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 20.3 | kcal/mol | PHPMS | Sieck and Meot-ner, 1989 | gas phase; M |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrS° | 26.2 | cal/mol*K | PHPMS | Sieck and Meot-ner, 1989 | gas phase; M |
+
= (
•
)
By formula: C6H5S- + CH4O = (C6H5S- • CH4O)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 13.4 | kcal/mol | PHPMS | Sieck and Meot-ner, 1989 | gas phase; M |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrS° | 23.0 | cal/mol*K | PHPMS | Sieck and Meot-ner, 1989 | gas phase; M |
+
= (
•
)
By formula: C6H5S- + C3H8O = (C6H5S- • C3H8O)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 15.0 | kcal/mol | PHPMS | Sieck and Meot-ner, 1989 | gas phase; M |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrS° | 26.0 | cal/mol*K | PHPMS | Sieck and Meot-ner, 1989 | gas phase; M |
+
= (
•
)
By formula: C6H5S- + C4H10O = (C6H5S- • C4H10O)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 14.6 | kcal/mol | PHPMS | Sieck and Meot-ner, 1989 | gas phase; M |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrS° | 25.0 | cal/mol*K | PHPMS | Sieck and Meot-ner, 1989 | gas phase; M |
+
= (
•
)
By formula: C6H5S- + C2H3F3O = (C6H5S- • C2H3F3O)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 21.0 | kcal/mol | PHPMS | Sieck and Meot-ner, 1989 | gas phase; M |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrS° | 25.1 | cal/mol*K | PHPMS | Sieck and Meot-ner, 1989 | gas phase; M |
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
Protonation reactions
+
=
By formula: C6H5S- + H+ = C6H6S
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 340.4 ± 2.1 | kcal/mol | G+TS | Taft and Bordwell, 1988 | gas phase |
| ΔrH° | >340.1 ± 1.8 | kcal/mol | D-EA | Richardson, Stephenson, et al., 1975 | gas phase |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 333.4 ± 2.1 | kcal/mol | IMRE | Guillemin, Riague, et al., 2005 | gas phase |
| ΔrG° | 333.8 ± 2.0 | kcal/mol | IMRE | Taft and Bordwell, 1988 | gas phase |
| ΔrG° | >333.5 ± 1.9 | kcal/mol | H-TS | Richardson, Stephenson, et al., 1975 | gas phase |
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.
Taft and Bordwell, 1988
Taft, R.W.; Bordwell, F.G.,
Structural and Solvent Effects Evaluated from Acidities Measured in Dimethyl Sulfoxide and in the Gas Phase,
Acc. Chem. Res., 1988, 21, 12, 463, https://doi.org/10.1021/ar00156a005
. [all data]
Richardson, Stephenson, et al., 1975
Richardson, J.H.; Stephenson, L.M.; Brauman, J.I.,
Photodetachment of electrons from phenoxides and thiophenoxide,
J. Am. Chem. Soc., 1975, 97, 2967. [all data]
Guillemin, Riague, et al., 2005
Guillemin, J.C.; Riague, E.H.; Gal, J.F.; Maria, P.C.; Mo, O.; Yanez, M.,
Acidity trends in alpha,beta-unsaturated sulfur, selenium, and tellurium derivatives: Comparison with C-, Si-, Ge-, Sn-, N-, P-, As-, and Sb-containing analogues,
Chem. Eur. J., 2005, 11, 7, 2145-2153, https://doi.org/10.1002/chem.200400989
. [all data]
Sieck and Meot-ner, 1989
Sieck, L.W.; Meot-ner, M.,
Ionic Hydrogen Bond and Ion Solvation. 8. RS-..HOR Bond Strengths. Correlation with Acidities.,
J. Phys. Chem., 1989, 93, 4, 1586, https://doi.org/10.1021/j100341a079
. [all data]
Notes
Go To: Top, Reaction thermochemistry data, Gas phase ion energetics 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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