thiophenoxide anion


Reaction thermochemistry data

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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

thiophenoxide anion + Hydrogen cation = Benzenethiol

By formula: C6H5S- + H+ = C6H6S

Quantity Value Units Method Reference Comment
Δr340.4 ± 2.1kcal/molG+TSTaft and Bordwell, 1988gas phase; B
Δr>340.1 ± 1.8kcal/molD-EARichardson, Stephenson, et al., 1975gas phase; B
Quantity Value Units Method Reference Comment
Δr333.4 ± 2.1kcal/molIMREGuillemin, Riague, et al., 2005gas phase; B
Δr333.8 ± 2.0kcal/molIMRETaft and Bordwell, 1988gas phase; B
Δr>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
Δr11.40 ± 0.20kcal/molTDAsSieck and Meot-ner, 1989gas phase; B
Quantity Value Units Method Reference Comment
Δr5.60 ± 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
Δr20.30 ± 0.10kcal/molTDAsSieck and Meot-ner, 1989gas phase; B
Quantity Value Units Method Reference Comment
Δr12.50 ± 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
Δr21.00 ± 0.20kcal/molTDAsSieck and Meot-ner, 1989gas phase; B
Quantity Value Units Method Reference Comment
Δr13.50 ± 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
Δr13.40 ± 0.10kcal/molTDAsSieck and Meot-ner, 1989gas phase; B
Quantity Value Units Method Reference Comment
Δr6.50 ± 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
Δr15.00 ± 0.10kcal/molTDAsSieck and Meot-ner, 1989gas phase; B
Quantity Value Units Method Reference Comment
Δr7.30 ± 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
Δr14.60 ± 0.10kcal/molTDAsSieck and Meot-ner, 1989gas phase; B
Quantity Value Units Method Reference Comment
Δr7.20 ± 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
Δr20.00 ± 0.40kcal/molTDAsSieck and Meot-ner, 1989gas phase; B
Quantity Value Units Method Reference Comment
Δr12.4 ± 1.3kcal/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
Δr11.4kcal/molPHPMSSieck and Meot-ner, 1989gas phase; M
Quantity Value Units Method Reference Comment
Δr19.6cal/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
Δr20.0kcal/molPHPMSSieck and Meot-ner, 1989gas phase; M
Quantity Value Units Method Reference Comment
Δr25.6cal/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
Δr20.3kcal/molPHPMSSieck and Meot-ner, 1989gas phase; M
Quantity Value Units Method Reference Comment
Δr26.2cal/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
Δr13.4kcal/molPHPMSSieck and Meot-ner, 1989gas phase; M
Quantity Value Units Method Reference Comment
Δr23.0cal/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
Δr15.0kcal/molPHPMSSieck and Meot-ner, 1989gas phase; M
Quantity Value Units Method Reference Comment
Δr26.0cal/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
Δr14.6kcal/molPHPMSSieck and Meot-ner, 1989gas phase; M
Quantity Value Units Method Reference Comment
Δr25.0cal/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
Δr21.0kcal/molPHPMSSieck and Meot-ner, 1989gas phase; M
Quantity Value Units Method Reference Comment
Δr25.1cal/mol*KPHPMSSieck and Meot-ner, 1989gas 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

thiophenoxide anion + Hydrogen cation = Benzenethiol

By formula: C6H5S- + H+ = C6H6S

Quantity Value Units Method Reference Comment
Δr340.4 ± 2.1kcal/molG+TSTaft and Bordwell, 1988gas phase
Δr>340.1 ± 1.8kcal/molD-EARichardson, Stephenson, et al., 1975gas phase
Quantity Value Units Method Reference Comment
Δr333.4 ± 2.1kcal/molIMREGuillemin, Riague, et al., 2005gas phase
Δr333.8 ± 2.0kcal/molIMRETaft and Bordwell, 1988gas phase
Δr>333.5 ± 1.9kcal/molH-TSRichardson, Stephenson, et al., 1975gas 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

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