cyclopentadienide anion

• Formula: C₅H₅^-
• Molecular weight: 65.0937
• IUPAC Standard InChI: InChI=1S/C5H5/c1-2-4-5-3-1/h1-5H/q-1 Copy

  
• IUPAC Standard InChIKey: SINKOGOPEQSHQD-UHFFFAOYSA-N Copy
• CAS Registry Number: 12127-83-2
• Chemical structure:
  This structure is also available as a 2d Mol file or as a computed 3d SD file
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• Information on this page:
  • Gas phase ion energetics data
  • Ion clustering data
  • References
  • Notes
• Other data available:
  • Reaction thermochemistry data
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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: C₅H₅^- + H⁺ = C₅H₆

Ion clustering 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

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

 + CCoO = C₆H₅CoO^-

By formula: C₅H₅^- + CCoO = C₆H₅CoO^-

 +  = ( • )

By formula: C₅H₅^- + CH₄O = (C₅H₅^- • CH₄O)

 + C₂D₃N = ( • C₂D₃N)

By formula: C₅H₅^- + C₂D₃N = (C₅H₅^- • C₂D₃N)

( • C₂D₃N) + C₂D₃N = ( • 2C₂D₃N)

By formula: (C₅H₅^- • C₂D₃N) + C₂D₃N = (C₅H₅^- • 2C₂D₃N)

( • 2C₂D₃N) + C₂D₃N = ( • 3C₂D₃N)

By formula: (C₅H₅^- • 2C₂D₃N) + C₂D₃N = (C₅H₅^- • 3C₂D₃N)

Free energy of reaction

 +  = ( • )

By formula: C₅H₅^- + C₂H₃F₃O = (C₅H₅^- • C₂H₃F₃O)

 +  = ( • )

By formula: C₅H₅^- + C₂H₃N = (C₅H₅^- • C₂H₃N)

 +  = ( • )

By formula: C₅H₅^- + C₃H₆O = (C₅H₅^- • C₃H₆O)

( • ) +  = ( • 2)

By formula: (C₅H₅^- • C₃H₆O) + C₃H₆O = (C₅H₅^- • 2C₃H₆O)

 +  = ( • )

By formula: C₅H₅^- + C₄H₁₀O = (C₅H₅^- • C₄H₁₀O)

 +  = ( • )

By formula: C₅H₅^- + C₅H₆ = (C₅H₅^- • C₅H₆)

Free energy of reaction

 +  = ( • )

By formula: C₅H₅^- + C₇H₈O = (C₅H₅^- • C₇H₈O)

 +  = C₅H₅Co^-

By formula: C₅H₅^- + Co = C₅H₅Co^-

 +  = ( • )

By formula: C₅H₅^- + H₂O = (C₅H₅^- • H₂O)

( • ) +  = ( • 2)

By formula: (C₅H₅^- • H₂O) + H₂O = (C₅H₅^- • 2H₂O)

References

Go To: Top, 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.

Bartmess, Scott, et al., 1979
Bartmess, J.E.; Scott, J.A.; McIver, R.T., Jr., The gas phase acidity scale from methanol to phenol, J. Am. Chem. Soc., 1979, 101, 6047. [all data]

Cumming and Kebarle, 1978
Cumming, J.B.; Kebarle, P., Summary of gas phase measurements involving acids AH. Entropy changes in proton transfer reactions involving negative ions. Bond dissociation energies D(A-H) and electron affinities EA(A), Can. J. Chem., 1978, 56, 1. [all data]

Engelking and Lineberger, 1977
Engelking, P.C.; Lineberger, W.C., Laser photoelectron spectrometry of C₅H₅-: A determination of the electron affinity and Jahn-Teller coupling in cyclopentadienyl, J. Chem. Phys., 1977, 67, 1412. [all data]

Sunderlin and Squires, 1999
Sunderlin, L.S.; Squires, R.R., Bond strengths in cyclopentadienyl metal carbonyl anions, Int. J. Mass Spectrom., 1999, 183, 149-161, https://doi.org/10.1016/S1387-3806(98)14230-6 . [all data]

Meot-ner, 1988
Meot-ner, M., The Ionic Hydrogen Bond and Solvation. 7. Interaction Energies of Carbanions with Solvent Molecules, J. Am. Chem. Soc., 1988, 110, 12, 3858, https://doi.org/10.1021/ja00220a022 . [all data]

Notes

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

• Symbols used in this document:
  

  T	Temperature
  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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