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 Copy

  
• IUPAC Standard InChIKey: RMVRSNDYEFQCLF-UHFFFAOYSA-M Copy
• 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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• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • Ion clustering data
  • References
  • Notes
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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

 +  =

By formula: C₆H₅S^- + H⁺ = C₆H₆S

 +  = C₆H₇OS^-

By formula: C₆H₅S^- + H₂O = C₆H₇OS^-

 +  = C₈H₉O₂S^-

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

 +  = C₈H₈F₃OS^-

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

 +  = C₇H₉OS^-

By formula: C₆H₅S^- + CH₄O = C₇H₉OS^-

 +  = C₉H₁₃OS^-

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

 +  = C₁₀H₁₅OS^-

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

 +  = C₉H₁₁O₂S^-

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

 +  = ( • )

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

 +  = ( • )

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

 +  = ( • )

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

 +  = ( • )

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

 +  = ( • )

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

 +  = ( • )

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

 +  = ( • )

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

Gas phase ion energetics 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 by: John E. Bartmess

Protonation reactions

 +  =

By formula: C₆H₅S^- + H⁺ = C₆H₆S

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

 +  = ( • )

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

 +  = C₇H₉OS^-

By formula: C₆H₅S^- + CH₄O = C₇H₉OS^-

 +  = ( • )

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

 +  = C₈H₈F₃OS^-

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

 +  = ( • )

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

 +  = C₈H₉O₂S^-

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

 +  = C₉H₁₁O₂S^-

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

 +  = ( • )

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

 +  = C₉H₁₃OS^-

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

 +  = ( • )

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

 +  = ( • )

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

 +  = C₁₀H₁₅OS^-

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

 +  = ( • )

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

 +  = C₆H₇OS^-

By formula: C₆H₅S^- + H₂O = C₆H₇OS^-

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

• 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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