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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
Deltar340.4 ± 2.1kcal/molG+TSTaft and Bordwell, 1988gas phase; B
Deltar>340.1 ± 1.8kcal/molD-EARichardson, Stephenson, et al., 1975gas phase; B
Quantity Value Units Method Reference Comment
Deltar333.4 ± 2.1kcal/molIMREGuillemin, Riague, et al., 2005gas phase; B
Deltar333.8 ± 2.0kcal/molIMRETaft and Bordwell, 1988gas phase; B
Deltar>333.5 ± 1.9kcal/molH-TSRichardson, Stephenson, et al., 1975gas phase; B

thiophenoxide anion + Water = C6H7OS-

By formula: C6H5S- + H2O = C6H7OS-

Quantity Value Units Method Reference Comment
Deltar11.40 ± 0.20kcal/molTDAsSieck and Meot-ner, 1989gas phase; B
Quantity Value Units Method Reference Comment
Deltar5.60 ± 0.70kcal/molTDAsSieck and Meot-ner, 1989gas phase; B

thiophenoxide anion + Acetic acid = C8H9O2S-

By formula: C6H5S- + C2H4O2 = C8H9O2S-

Quantity Value Units Method Reference Comment
Deltar20.30 ± 0.10kcal/molTDAsSieck and Meot-ner, 1989gas phase; B
Quantity Value Units Method Reference Comment
Deltar12.50 ± 0.40kcal/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
Deltar21.00 ± 0.20kcal/molTDAsSieck and Meot-ner, 1989gas phase; B
Quantity Value Units Method Reference Comment
Deltar13.50 ± 0.60kcal/molTDAsSieck and Meot-ner, 1989gas phase; B

thiophenoxide anion + Methyl Alcohol = C7H9OS-

By formula: C6H5S- + CH4O = C7H9OS-

Quantity Value Units Method Reference Comment
Deltar13.40 ± 0.10kcal/molTDAsSieck and Meot-ner, 1989gas phase; B
Quantity Value Units Method Reference Comment
Deltar6.50 ± 0.30kcal/molTDAsSieck and Meot-ner, 1989gas phase; B

thiophenoxide anion + Isopropyl Alcohol = C9H13OS-

By formula: C6H5S- + C3H8O = C9H13OS-

Quantity Value Units Method Reference Comment
Deltar15.00 ± 0.10kcal/molTDAsSieck and Meot-ner, 1989gas phase; B
Quantity Value Units Method Reference Comment
Deltar7.30 ± 0.40kcal/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
Deltar14.60 ± 0.10kcal/molTDAsSieck and Meot-ner, 1989gas phase; B
Quantity Value Units Method Reference Comment
Deltar7.20 ± 0.50kcal/molTDAsSieck and Meot-ner, 1989gas phase; B

thiophenoxide anion + Propanoic acid = C9H11O2S-

By formula: C6H5S- + C3H6O2 = C9H11O2S-

Quantity Value Units Method Reference Comment
Deltar20.00 ± 0.40kcal/molTDAsSieck and Meot-ner, 1989gas phase; B
Quantity Value Units Method Reference Comment
Deltar12.4 ± 1.3kcal/molTDAsSieck and Meot-ner, 1989gas phase; B

thiophenoxide anion + Water = (thiophenoxide anion bullet Water)

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

Quantity Value Units Method Reference Comment
Deltar11.4kcal/molPHPMSSieck and Meot-ner, 1989gas phase; M
Quantity Value Units Method Reference Comment
Deltar19.6cal/mol*KPHPMSSieck and Meot-ner, 1989gas phase; M

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

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

Quantity Value Units Method Reference Comment
Deltar20.0kcal/molPHPMSSieck and Meot-ner, 1989gas phase; M
Quantity Value Units Method Reference Comment
Deltar25.6cal/mol*KPHPMSSieck and Meot-ner, 1989gas phase; M

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

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

Quantity Value Units Method Reference Comment
Deltar20.3kcal/molPHPMSSieck and Meot-ner, 1989gas phase; M
Quantity Value Units Method Reference Comment
Deltar26.2cal/mol*KPHPMSSieck and Meot-ner, 1989gas phase; M

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

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

Quantity Value Units Method Reference Comment
Deltar13.4kcal/molPHPMSSieck and Meot-ner, 1989gas phase; M
Quantity Value Units Method Reference Comment
Deltar23.0cal/mol*KPHPMSSieck and Meot-ner, 1989gas phase; M

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

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

Quantity Value Units Method Reference Comment
Deltar15.0kcal/molPHPMSSieck and Meot-ner, 1989gas phase; M
Quantity Value Units Method Reference Comment
Deltar26.0cal/mol*KPHPMSSieck and Meot-ner, 1989gas phase; M

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

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

Quantity Value Units Method Reference Comment
Deltar14.6kcal/molPHPMSSieck and Meot-ner, 1989gas phase; M
Quantity Value Units Method Reference Comment
Deltar25.0cal/mol*KPHPMSSieck and Meot-ner, 1989gas phase; M

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

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

Quantity Value Units Method Reference Comment
Deltar21.0kcal/molPHPMSSieck and Meot-ner, 1989gas phase; M
Quantity Value Units Method Reference Comment
Deltar25.1cal/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
Deltar340.4 ± 2.1kcal/molG+TSTaft and Bordwell, 1988gas phase
Deltar>340.1 ± 1.8kcal/molD-EARichardson, Stephenson, et al., 1975gas phase
Quantity Value Units Method Reference Comment
Deltar333.4 ± 2.1kcal/molIMREGuillemin, Riague, et al., 2005gas phase
Deltar333.8 ± 2.0kcal/molIMRETaft and Bordwell, 1988gas phase
Deltar>333.5 ± 1.9kcal/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 bullet Methyl Alcohol)

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

Quantity Value Units Method Reference Comment
Deltar13.4kcal/molPHPMSSieck and Meot-ner, 1989gas phase; M
Quantity Value Units Method Reference Comment
Deltar23.0cal/mol*KPHPMSSieck and Meot-ner, 1989gas phase; M

thiophenoxide anion + Methyl Alcohol = C7H9OS-

By formula: C6H5S- + CH4O = C7H9OS-

Quantity Value Units Method Reference Comment
Deltar13.40 ± 0.10kcal/molTDAsSieck and Meot-ner, 1989gas phase; B
Quantity Value Units Method Reference Comment
Deltar6.50 ± 0.30kcal/molTDAsSieck and Meot-ner, 1989gas phase; B

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

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

Quantity Value Units Method Reference Comment
Deltar21.0kcal/molPHPMSSieck and Meot-ner, 1989gas phase; M
Quantity Value Units Method Reference Comment
Deltar25.1cal/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
Deltar21.00 ± 0.20kcal/molTDAsSieck and Meot-ner, 1989gas phase; B
Quantity Value Units Method Reference Comment
Deltar13.50 ± 0.60kcal/molTDAsSieck and Meot-ner, 1989gas phase; B

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

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

Quantity Value Units Method Reference Comment
Deltar20.3kcal/molPHPMSSieck and Meot-ner, 1989gas phase; M
Quantity Value Units Method Reference Comment
Deltar26.2cal/mol*KPHPMSSieck and Meot-ner, 1989gas phase; M

thiophenoxide anion + Acetic acid = C8H9O2S-

By formula: C6H5S- + C2H4O2 = C8H9O2S-

Quantity Value Units Method Reference Comment
Deltar20.30 ± 0.10kcal/molTDAsSieck and Meot-ner, 1989gas phase; B
Quantity Value Units Method Reference Comment
Deltar12.50 ± 0.40kcal/molTDAsSieck and Meot-ner, 1989gas phase; B

thiophenoxide anion + Propanoic acid = C9H11O2S-

By formula: C6H5S- + C3H6O2 = C9H11O2S-

Quantity Value Units Method Reference Comment
Deltar20.00 ± 0.40kcal/molTDAsSieck and Meot-ner, 1989gas phase; B
Quantity Value Units Method Reference Comment
Deltar12.4 ± 1.3kcal/molTDAsSieck and Meot-ner, 1989gas phase; B

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

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

Quantity Value Units Method Reference Comment
Deltar20.0kcal/molPHPMSSieck and Meot-ner, 1989gas phase; M
Quantity Value Units Method Reference Comment
Deltar25.6cal/mol*KPHPMSSieck and Meot-ner, 1989gas phase; M

thiophenoxide anion + Isopropyl Alcohol = C9H13OS-

By formula: C6H5S- + C3H8O = C9H13OS-

Quantity Value Units Method Reference Comment
Deltar15.00 ± 0.10kcal/molTDAsSieck and Meot-ner, 1989gas phase; B
Quantity Value Units Method Reference Comment
Deltar7.30 ± 0.40kcal/molTDAsSieck and Meot-ner, 1989gas phase; B

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

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

Quantity Value Units Method Reference Comment
Deltar15.0kcal/molPHPMSSieck and Meot-ner, 1989gas phase; M
Quantity Value Units Method Reference Comment
Deltar26.0cal/mol*KPHPMSSieck and Meot-ner, 1989gas phase; M

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

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

Quantity Value Units Method Reference Comment
Deltar14.6kcal/molPHPMSSieck and Meot-ner, 1989gas phase; M
Quantity Value Units Method Reference Comment
Deltar25.0cal/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
Deltar14.60 ± 0.10kcal/molTDAsSieck and Meot-ner, 1989gas phase; B
Quantity Value Units Method Reference Comment
Deltar7.20 ± 0.50kcal/molTDAsSieck and Meot-ner, 1989gas phase; B

thiophenoxide anion + Water = (thiophenoxide anion bullet Water)

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

Quantity Value Units Method Reference Comment
Deltar11.4kcal/molPHPMSSieck and Meot-ner, 1989gas phase; M
Quantity Value Units Method Reference Comment
Deltar19.6cal/mol*KPHPMSSieck and Meot-ner, 1989gas phase; M

thiophenoxide anion + Water = C6H7OS-

By formula: C6H5S- + H2O = C6H7OS-

Quantity Value Units Method Reference Comment
Deltar11.40 ± 0.20kcal/molTDAsSieck and Meot-ner, 1989gas phase; B
Quantity Value Units Method Reference Comment
Deltar5.60 ± 0.70kcal/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