thiophenoxide anion


Reaction thermochemistry data

Go To: Top, Gas phase ion energetics data, Ion clustering 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

thiophenoxide anion + Hydrogen cation = Benzenethiol

By formula: C6H5S- + H+ = C6H6S

Quantity Value Units Method Reference Comment
Δr1424. ± 8.8kJ/molG+TSTaft and Bordwell, 1988gas phase; B
Δr>1423. ± 7.5kJ/molD-EARichardson, Stephenson, et al., 1975gas phase; B
Quantity Value Units Method Reference Comment
Δr1395. ± 8.8kJ/molIMREGuillemin, Riague, et al., 2005gas phase; B
Δr1397. ± 8.4kJ/molIMRETaft and Bordwell, 1988gas phase; B
Δr>1395. ± 7.9kJ/molH-TSRichardson, Stephenson, et al., 1975gas phase; B

thiophenoxide anion + Water = C6H7OS-

By formula: C6H5S- + H2O = C6H7OS-

Quantity Value Units Method Reference Comment
Δr47.70 ± 0.84kJ/molTDAsSieck and Meot-ner, 1989gas phase; B
Quantity Value Units Method Reference Comment
Δr23.4 ± 2.9kJ/molTDAsSieck and Meot-ner, 1989gas phase; B

thiophenoxide anion + Acetic acid = C8H9O2S-

By formula: C6H5S- + C2H4O2 = C8H9O2S-

Quantity Value Units Method Reference Comment
Δr84.94 ± 0.42kJ/molTDAsSieck and Meot-ner, 1989gas phase; B
Quantity Value Units Method Reference Comment
Δr52.3 ± 1.7kJ/molTDAsSieck and Meot-ner, 1989gas phase; B

thiophenoxide anion + Ethanol, 2,2,2-trifluoro- = C8H8F3OS-

By formula: C6H5S- + C2H3F3O = C8H8F3OS-

Quantity Value Units Method Reference Comment
Δr87.86 ± 0.84kJ/molTDAsSieck and Meot-ner, 1989gas phase; B
Quantity Value Units Method Reference Comment
Δr56.5 ± 2.5kJ/molTDAsSieck and Meot-ner, 1989gas phase; B

thiophenoxide anion + Methyl Alcohol = C7H9OS-

By formula: C6H5S- + CH4O = C7H9OS-

Quantity Value Units Method Reference Comment
Δr56.07 ± 0.42kJ/molTDAsSieck and Meot-ner, 1989gas phase; B
Quantity Value Units Method Reference Comment
Δr27.2 ± 1.3kJ/molTDAsSieck and Meot-ner, 1989gas phase; B

thiophenoxide anion + Isopropyl Alcohol = C9H13OS-

By formula: C6H5S- + C3H8O = C9H13OS-

Quantity Value Units Method Reference Comment
Δr62.76 ± 0.42kJ/molTDAsSieck and Meot-ner, 1989gas phase; B
Quantity Value Units Method Reference Comment
Δr30.5 ± 1.7kJ/molTDAsSieck and Meot-ner, 1989gas phase; B

thiophenoxide anion + 2-Propanol, 2-methyl- = C10H15OS-

By formula: C6H5S- + C4H10O = C10H15OS-

Quantity Value Units Method Reference Comment
Δr61.09 ± 0.42kJ/molTDAsSieck and Meot-ner, 1989gas phase; B
Quantity Value Units Method Reference Comment
Δr30.1 ± 2.1kJ/molTDAsSieck and Meot-ner, 1989gas phase; B

thiophenoxide anion + Propanoic acid = C9H11O2S-

By formula: C6H5S- + C3H6O2 = C9H11O2S-

Quantity Value Units Method Reference Comment
Δr83.7 ± 1.7kJ/molTDAsSieck and Meot-ner, 1989gas phase; B
Quantity Value Units Method Reference Comment
Δr51.9 ± 5.4kJ/molTDAsSieck and Meot-ner, 1989gas phase; B

thiophenoxide anion + Water = (thiophenoxide anion • Water)

By formula: C6H5S- + H2O = (C6H5S- • H2O)

Quantity Value Units Method Reference Comment
Δr47.7kJ/molPHPMSSieck and Meot-ner, 1989gas phase; M
Quantity Value Units Method Reference Comment
Δr82.0J/mol*KPHPMSSieck and Meot-ner, 1989gas phase; M

thiophenoxide anion + Ethyl formate = (thiophenoxide anion • Ethyl formate)

By formula: C6H5S- + C3H6O2 = (C6H5S- • C3H6O2)

Quantity Value Units Method Reference Comment
Δr83.7kJ/molPHPMSSieck and Meot-ner, 1989gas phase; M
Quantity Value Units Method Reference Comment
Δr107.J/mol*KPHPMSSieck and Meot-ner, 1989gas phase; M

thiophenoxide anion + Acetic acid = (thiophenoxide anion • Acetic acid)

By formula: C6H5S- + C2H4O2 = (C6H5S- • C2H4O2)

Quantity Value Units Method Reference Comment
Δr84.9kJ/molPHPMSSieck and Meot-ner, 1989gas phase; M
Quantity Value Units Method Reference Comment
Δr110.J/mol*KPHPMSSieck and Meot-ner, 1989gas phase; M

thiophenoxide anion + Methyl Alcohol = (thiophenoxide anion • Methyl Alcohol)

By formula: C6H5S- + CH4O = (C6H5S- • CH4O)

Quantity Value Units Method Reference Comment
Δr56.1kJ/molPHPMSSieck and Meot-ner, 1989gas phase; M
Quantity Value Units Method Reference Comment
Δr96.2J/mol*KPHPMSSieck and Meot-ner, 1989gas phase; M

thiophenoxide anion + 1-Propanol = (thiophenoxide anion • 1-Propanol)

By formula: C6H5S- + C3H8O = (C6H5S- • C3H8O)

Quantity Value Units Method Reference Comment
Δr62.8kJ/molPHPMSSieck and Meot-ner, 1989gas phase; M
Quantity Value Units Method Reference Comment
Δr109.J/mol*KPHPMSSieck and Meot-ner, 1989gas phase; M

thiophenoxide anion + 1-Butanol = (thiophenoxide anion • 1-Butanol)

By formula: C6H5S- + C4H10O = (C6H5S- • C4H10O)

Quantity Value Units Method Reference Comment
Δr61.1kJ/molPHPMSSieck and Meot-ner, 1989gas phase; M
Quantity Value Units Method Reference Comment
Δr105.J/mol*KPHPMSSieck and Meot-ner, 1989gas phase; M

thiophenoxide anion + Ethanol, 2,2,2-trifluoro- = (thiophenoxide anion • Ethanol, 2,2,2-trifluoro-)

By formula: C6H5S- + C2H3F3O = (C6H5S- • C2H3F3O)

Quantity Value Units Method Reference Comment
Δr87.9kJ/molPHPMSSieck and Meot-ner, 1989gas phase; M
Quantity Value Units Method Reference Comment
Δr105.J/mol*KPHPMSSieck and Meot-ner, 1989gas phase; M

Gas phase ion energetics data

Go To: Top, Reaction thermochemistry data, Ion clustering 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

thiophenoxide anion + Hydrogen cation = Benzenethiol

By formula: C6H5S- + H+ = C6H6S

Quantity Value Units Method Reference Comment
Δr1424. ± 8.8kJ/molG+TSTaft and Bordwell, 1988gas phase
Δr>1423. ± 7.5kJ/molD-EARichardson, Stephenson, et al., 1975gas phase
Quantity Value Units Method Reference Comment
Δr1395. ± 8.8kJ/molIMREGuillemin, Riague, et al., 2005gas phase
Δr1397. ± 8.4kJ/molIMRETaft and Bordwell, 1988gas phase
Δr>1395. ± 7.9kJ/molH-TSRichardson, Stephenson, et al., 1975gas phase

Ion clustering data

Go To: Top, Reaction thermochemistry 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 as indicated in comments:
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
B - John E. Bartmess

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. Searches may be limited to ion clustering reactions. A general reaction search form is also available.

Clustering reactions

thiophenoxide anion + Methyl Alcohol = (thiophenoxide anion • Methyl Alcohol)

By formula: C6H5S- + CH4O = (C6H5S- • CH4O)

Quantity Value Units Method Reference Comment
Δr56.1kJ/molPHPMSSieck and Meot-ner, 1989gas phase; M
Quantity Value Units Method Reference Comment
Δr96.2J/mol*KPHPMSSieck and Meot-ner, 1989gas phase; M

thiophenoxide anion + Methyl Alcohol = C7H9OS-

By formula: C6H5S- + CH4O = C7H9OS-

Quantity Value Units Method Reference Comment
Δr56.07 ± 0.42kJ/molTDAsSieck and Meot-ner, 1989gas phase; B
Quantity Value Units Method Reference Comment
Δr27.2 ± 1.3kJ/molTDAsSieck and Meot-ner, 1989gas phase; B

thiophenoxide anion + Ethanol, 2,2,2-trifluoro- = (thiophenoxide anion • Ethanol, 2,2,2-trifluoro-)

By formula: C6H5S- + C2H3F3O = (C6H5S- • C2H3F3O)

Quantity Value Units Method Reference Comment
Δr87.9kJ/molPHPMSSieck and Meot-ner, 1989gas phase; M
Quantity Value Units Method Reference Comment
Δr105.J/mol*KPHPMSSieck and Meot-ner, 1989gas phase; M

thiophenoxide anion + Ethanol, 2,2,2-trifluoro- = C8H8F3OS-

By formula: C6H5S- + C2H3F3O = C8H8F3OS-

Quantity Value Units Method Reference Comment
Δr87.86 ± 0.84kJ/molTDAsSieck and Meot-ner, 1989gas phase; B
Quantity Value Units Method Reference Comment
Δr56.5 ± 2.5kJ/molTDAsSieck and Meot-ner, 1989gas phase; B

thiophenoxide anion + Acetic acid = (thiophenoxide anion • Acetic acid)

By formula: C6H5S- + C2H4O2 = (C6H5S- • C2H4O2)

Quantity Value Units Method Reference Comment
Δr84.9kJ/molPHPMSSieck and Meot-ner, 1989gas phase; M
Quantity Value Units Method Reference Comment
Δr110.J/mol*KPHPMSSieck and Meot-ner, 1989gas phase; M

thiophenoxide anion + Acetic acid = C8H9O2S-

By formula: C6H5S- + C2H4O2 = C8H9O2S-

Quantity Value Units Method Reference Comment
Δr84.94 ± 0.42kJ/molTDAsSieck and Meot-ner, 1989gas phase; B
Quantity Value Units Method Reference Comment
Δr52.3 ± 1.7kJ/molTDAsSieck and Meot-ner, 1989gas phase; B

thiophenoxide anion + Propanoic acid = C9H11O2S-

By formula: C6H5S- + C3H6O2 = C9H11O2S-

Quantity Value Units Method Reference Comment
Δr83.7 ± 1.7kJ/molTDAsSieck and Meot-ner, 1989gas phase; B
Quantity Value Units Method Reference Comment
Δr51.9 ± 5.4kJ/molTDAsSieck and Meot-ner, 1989gas phase; B

thiophenoxide anion + Ethyl formate = (thiophenoxide anion • Ethyl formate)

By formula: C6H5S- + C3H6O2 = (C6H5S- • C3H6O2)

Quantity Value Units Method Reference Comment
Δr83.7kJ/molPHPMSSieck and Meot-ner, 1989gas phase; M
Quantity Value Units Method Reference Comment
Δr107.J/mol*KPHPMSSieck and Meot-ner, 1989gas phase; M

thiophenoxide anion + Isopropyl Alcohol = C9H13OS-

By formula: C6H5S- + C3H8O = C9H13OS-

Quantity Value Units Method Reference Comment
Δr62.76 ± 0.42kJ/molTDAsSieck and Meot-ner, 1989gas phase; B
Quantity Value Units Method Reference Comment
Δr30.5 ± 1.7kJ/molTDAsSieck and Meot-ner, 1989gas phase; B

thiophenoxide anion + 1-Propanol = (thiophenoxide anion • 1-Propanol)

By formula: C6H5S- + C3H8O = (C6H5S- • C3H8O)

Quantity Value Units Method Reference Comment
Δr62.8kJ/molPHPMSSieck and Meot-ner, 1989gas phase; M
Quantity Value Units Method Reference Comment
Δr109.J/mol*KPHPMSSieck and Meot-ner, 1989gas phase; M

thiophenoxide anion + 1-Butanol = (thiophenoxide anion • 1-Butanol)

By formula: C6H5S- + C4H10O = (C6H5S- • C4H10O)

Quantity Value Units Method Reference Comment
Δr61.1kJ/molPHPMSSieck and Meot-ner, 1989gas phase; M
Quantity Value Units Method Reference Comment
Δr105.J/mol*KPHPMSSieck and Meot-ner, 1989gas phase; M

thiophenoxide anion + 2-Propanol, 2-methyl- = C10H15OS-

By formula: C6H5S- + C4H10O = C10H15OS-

Quantity Value Units Method Reference Comment
Δr61.09 ± 0.42kJ/molTDAsSieck and Meot-ner, 1989gas phase; B
Quantity Value Units Method Reference Comment
Δr30.1 ± 2.1kJ/molTDAsSieck and Meot-ner, 1989gas phase; B

thiophenoxide anion + Water = (thiophenoxide anion • Water)

By formula: C6H5S- + H2O = (C6H5S- • H2O)

Quantity Value Units Method Reference Comment
Δr47.7kJ/molPHPMSSieck and Meot-ner, 1989gas phase; M
Quantity Value Units Method Reference Comment
Δr82.0J/mol*KPHPMSSieck and Meot-ner, 1989gas phase; M

thiophenoxide anion + Water = C6H7OS-

By formula: C6H5S- + H2O = C6H7OS-

Quantity Value Units Method Reference Comment
Δr47.70 ± 0.84kJ/molTDAsSieck and Meot-ner, 1989gas phase; B
Quantity Value Units Method Reference Comment
Δr23.4 ± 2.9kJ/molTDAsSieck and Meot-ner, 1989gas phase; B

References

Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering 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, Ion clustering data, References