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:
This structure is also available as a 2d Mol file or as a computed 3d SD file
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Other data available:
- Gas phase ion energetics data
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Reaction thermochemistry data

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 + =

By formula: C₆H₅S^- + H⁺ = C₆H₆S

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	1424. ± 8.8	kJ/mol	G+TS	Taft and Bordwell, 1988	gas phase; B
Δ_rH°	>1423. ± 7.5	kJ/mol	D-EA	Richardson, Stephenson, et al., 1975	gas phase; B
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	1395. ± 8.8	kJ/mol	IMRE	Guillemin, Riague, et al., 2005	gas phase; B
Δ_rG°	1397. ± 8.4	kJ/mol	IMRE	Taft and Bordwell, 1988	gas phase; B
Δ_rG°	>1395. ± 7.9	kJ/mol	H-TS	Richardson, Stephenson, et al., 1975	gas phase; B

thiophenoxide anion + = C₆H₇OS^-

By formula: C₆H₅S^- + H₂O = C₆H₇OS^-

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	47.70 ± 0.84	kJ/mol	TDAs	Sieck and Meot-ner, 1989	gas phase; B
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	23.4 ± 2.9	kJ/mol	TDAs	Sieck and Meot-ner, 1989	gas phase; B

thiophenoxide anion + = C₈H₉O₂S^-

By formula: C₆H₅S^- + C₂H₄O₂ = C₈H₉O₂S^-

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	84.94 ± 0.42	kJ/mol	TDAs	Sieck and Meot-ner, 1989	gas phase; B
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	52.3 ± 1.7	kJ/mol	TDAs	Sieck and Meot-ner, 1989	gas phase; B

thiophenoxide anion + = C₈H₈F₃OS^-

By formula: C₆H₅S^- + C₂H₃F₃O = C₈H₈F₃OS^-

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	87.86 ± 0.84	kJ/mol	TDAs	Sieck and Meot-ner, 1989	gas phase; B
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	56.5 ± 2.5	kJ/mol	TDAs	Sieck and Meot-ner, 1989	gas phase; B

thiophenoxide anion + = C₇H₉OS^-

By formula: C₆H₅S^- + CH₄O = C₇H₉OS^-

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	56.07 ± 0.42	kJ/mol	TDAs	Sieck and Meot-ner, 1989	gas phase; B
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	27.2 ± 1.3	kJ/mol	TDAs	Sieck and Meot-ner, 1989	gas phase; B

thiophenoxide anion + = C₉H₁₃OS^-

By formula: C₆H₅S^- + C₃H₈O = C₉H₁₃OS^-

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	62.76 ± 0.42	kJ/mol	TDAs	Sieck and Meot-ner, 1989	gas phase; B
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	30.5 ± 1.7	kJ/mol	TDAs	Sieck and Meot-ner, 1989	gas phase; B

thiophenoxide anion + = C₁₀H₁₅OS^-

By formula: C₆H₅S^- + C₄H₁₀O = C₁₀H₁₅OS^-

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	61.09 ± 0.42	kJ/mol	TDAs	Sieck and Meot-ner, 1989	gas phase; B
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	30.1 ± 2.1	kJ/mol	TDAs	Sieck and Meot-ner, 1989	gas phase; B

thiophenoxide anion + = C₉H₁₁O₂S^-

By formula: C₆H₅S^- + C₃H₆O₂ = C₉H₁₁O₂S^-

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	83.7 ± 1.7	kJ/mol	TDAs	Sieck and Meot-ner, 1989	gas phase; B
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	51.9 ± 5.4	kJ/mol	TDAs	Sieck and Meot-ner, 1989	gas phase; B

thiophenoxide anion + = ( • )

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

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	47.7	kJ/mol	PHPMS	Sieck and Meot-ner, 1989	gas phase; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	82.0	J/mol*K	PHPMS	Sieck and Meot-ner, 1989	gas phase; M

thiophenoxide anion + = ( • )

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

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	83.7	kJ/mol	PHPMS	Sieck and Meot-ner, 1989	gas phase; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	107.	J/mol*K	PHPMS	Sieck and Meot-ner, 1989	gas phase; M

thiophenoxide anion + = ( • )

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

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	84.9	kJ/mol	PHPMS	Sieck and Meot-ner, 1989	gas phase; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	110.	J/mol*K	PHPMS	Sieck and Meot-ner, 1989	gas phase; M

thiophenoxide anion + = ( • )

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

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	56.1	kJ/mol	PHPMS	Sieck and Meot-ner, 1989	gas phase; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	96.2	J/mol*K	PHPMS	Sieck and Meot-ner, 1989	gas phase; M

thiophenoxide anion + = ( • )

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

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	62.8	kJ/mol	PHPMS	Sieck and Meot-ner, 1989	gas phase; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	109.	J/mol*K	PHPMS	Sieck and Meot-ner, 1989	gas phase; M

thiophenoxide anion + = ( • )

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

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	61.1	kJ/mol	PHPMS	Sieck and Meot-ner, 1989	gas phase; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	105.	J/mol*K	PHPMS	Sieck and Meot-ner, 1989	gas phase; M

thiophenoxide anion + = ( • )

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

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	87.9	kJ/mol	PHPMS	Sieck and Meot-ner, 1989	gas phase; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	105.	J/mol*K	PHPMS	Sieck and Meot-ner, 1989	gas phase; M

References

Go To: Top, Reaction thermochemistry data, Notes

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, References

Symbols used in this document:

Δ_rG° Free energy of reaction at standard conditions

Δ_rH° Enthalpy of reaction at standard conditions

Δ_rS° Entropy of reaction at standard conditions
Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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Δ_rG°	Free energy of reaction at standard conditions
Δ_rH°	Enthalpy of reaction at standard conditions
Δ_rS°	Entropy of reaction at standard conditions