cyclopentadienide anion


Reaction thermochemistry data

Go To: Top, 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:
B - John E. Bartmess
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias

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Individual Reactions

cyclopentadienide anion + Hydrogen cation = 1,3-Cyclopentadiene

By formula: C5H5- + H+ = C5H6

Quantity Value Units Method Reference Comment
Δr1481. ± 9.2kJ/molG+TSBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B
Δr1485. ± 12.kJ/molG+TSCumming and Kebarle, 1978gas phase; B
Δr1495. ± 8.4kJ/molD-EAEngelking and Lineberger, 1977gas phase; B
Quantity Value Units Method Reference Comment
Δr1455. ± 8.4kJ/molIMREBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B
Δr1459. ± 8.4kJ/molIMRECumming and Kebarle, 1978gas phase; B

cyclopentadienide anion + 1,3-Cyclopentadiene = (cyclopentadienide anion • 1,3-Cyclopentadiene)

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

Quantity Value Units Method Reference Comment
Δr<36.0kJ/molIMRBMeot-ner, 1988gas phase; B,M
Quantity Value Units Method Reference Comment
Δr84.J/mol*KN/AMeot-ner, 1988gas phase; Entropy change calculated or estimated, DG<, ΔrH<; M
Quantity Value Units Method Reference Comment
Δr<11. ± 4.2kJ/molIMRBMeot-ner, 1988gas phase; B

Free energy of reaction

ΔrG° (kJ/mol) T (K) Method Reference Comment
15.250.PHPMSMeot-ner, 1988gas phase; Entropy change calculated or estimated, DG<, ΔrH<; M

(cyclopentadienide anion • 2C2D3N) + C2D3N = (cyclopentadienide anion • 3C2D3N)

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

Quantity Value Units Method Reference Comment
Δr42.7kJ/molPHPMSMeot-ner, 1988gas phase; Entropy change calculated or estimated, ΔrH<, CD3CN; M
Quantity Value Units Method Reference Comment
Δr92.J/mol*KN/AMeot-ner, 1988gas phase; Entropy change calculated or estimated, ΔrH<, CD3CN; M

Free energy of reaction

ΔrG° (kJ/mol) T (K) Method Reference Comment
21.232.PHPMSMeot-ner, 1988gas phase; Entropy change calculated or estimated, ΔrH<, CD3CN; M

cyclopentadienide anion + Water = (cyclopentadienide anion • Water)

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

Quantity Value Units Method Reference Comment
Δr46.0 ± 4.2kJ/molTDAsMeot-ner, 1988gas phase; B,M
Quantity Value Units Method Reference Comment
Δr67.4J/mol*KPHPMSMeot-ner, 1988gas phase; M
Quantity Value Units Method Reference Comment
Δr26. ± 4.2kJ/molTDAsMeot-ner, 1988gas phase; B

cyclopentadienide anion + Benzyl alcohol = (cyclopentadienide anion • Benzyl alcohol)

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

Quantity Value Units Method Reference Comment
Δr80.3 ± 4.2kJ/molTDAsMeot-ner, 1988gas phase; B,M
Quantity Value Units Method Reference Comment
Δr125.J/mol*KPHPMSMeot-ner, 1988gas phase; M
Quantity Value Units Method Reference Comment
Δr43.1 ± 4.2kJ/molTDAsMeot-ner, 1988gas phase; B

cyclopentadienide anion + Ethanol, 2,2,2-trifluoro- = (cyclopentadienide anion • Ethanol, 2,2,2-trifluoro-)

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

Quantity Value Units Method Reference Comment
Δr86.2 ± 4.2kJ/molTDAsMeot-ner, 1988gas phase; B,M
Quantity Value Units Method Reference Comment
Δr102.J/mol*KPHPMSMeot-ner, 1988gas phase; M
Quantity Value Units Method Reference Comment
Δr55.6 ± 4.2kJ/molTDAsMeot-ner, 1988gas phase; B

cyclopentadienide anion + Acetone = (cyclopentadienide anion • Acetone)

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

Quantity Value Units Method Reference Comment
Δr56.5 ± 4.2kJ/molTDAsMeot-ner, 1988gas phase; B,M
Quantity Value Units Method Reference Comment
Δr91.2J/mol*KPHPMSMeot-ner, 1988gas phase; M
Quantity Value Units Method Reference Comment
Δr29. ± 4.2kJ/molTDAsMeot-ner, 1988gas phase; B

cyclopentadienide anion + 2-Propanol, 2-methyl- = (cyclopentadienide anion • 2-Propanol, 2-methyl-)

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

Quantity Value Units Method Reference Comment
Δr71.1 ± 4.2kJ/molTDAsMeot-ner, 1988gas phase; B,M
Quantity Value Units Method Reference Comment
Δr134.J/mol*KPHPMSMeot-ner, 1988gas phase; M
Quantity Value Units Method Reference Comment
Δr31. ± 4.2kJ/molTDAsMeot-ner, 1988gas phase; B

(cyclopentadienide anion • C2D3N) + C2D3N = (cyclopentadienide anion • 2C2D3N)

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

Quantity Value Units Method Reference Comment
Δr54.8kJ/molPHPMSMeot-ner, 1988gas phase; CD3CN; M
Quantity Value Units Method Reference Comment
Δr95.4J/mol*KPHPMSMeot-ner, 1988gas phase; CD3CN; M

cyclopentadienide anion + Methyl Alcohol = (cyclopentadienide anion • Methyl Alcohol)

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

Quantity Value Units Method Reference Comment
Δr55.2 ± 4.2kJ/molTDAsMeot-ner, 1988gas phase; B
Quantity Value Units Method Reference Comment
Δr29. ± 4.2kJ/molTDAsMeot-ner, 1988gas phase; B

cyclopentadienide anion + Acetonitrile = (cyclopentadienide anion • Acetonitrile)

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

Quantity Value Units Method Reference Comment
Δr64.9 ± 4.2kJ/molTDAsMeot-ner, 1988gas phase; B
Quantity Value Units Method Reference Comment
Δr36. ± 4.2kJ/molTDAsMeot-ner, 1988gas phase; B

(cyclopentadienide anion • Water) + Water = (cyclopentadienide anion • 2Water)

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

Quantity Value Units Method Reference Comment
Δr41.8kJ/molPHPMSMeot-ner, 1988gas phase; M
Quantity Value Units Method Reference Comment
Δr72.8J/mol*KPHPMSMeot-ner, 1988gas phase; M

(cyclopentadienide anion • Acetone) + Acetone = (cyclopentadienide anion • 2Acetone)

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

Quantity Value Units Method Reference Comment
Δr41.kJ/molPHPMSMeot-ner, 1988gas phase; M
Quantity Value Units Method Reference Comment
Δr68.6J/mol*KPHPMSMeot-ner, 1988gas phase; M

cyclopentadienide anion + C2D3N = (cyclopentadienide anion • C2D3N)

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

Quantity Value Units Method Reference Comment
Δr64.9kJ/molPHPMSMeot-ner, 1988gas phase; M
Quantity Value Units Method Reference Comment
Δr95.4J/mol*KPHPMSMeot-ner, 1988gas phase; M

cyclopentadienide anion + CCoO = C6H5CoO-

By formula: C5H5- + CCoO = C6H5CoO-

Quantity Value Units Method Reference Comment
Δr42.7 ± 3.3kJ/molN/ASunderlin and Squires, 1999gas phase; B

cyclopentadienide anion + cobalt = C5H5Co-

By formula: C5H5- + Co = C5H5Co-

Quantity Value Units Method Reference Comment
Δr29.3 ± 2.5kJ/molN/ASunderlin and Squires, 1999gas phase; B

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

cyclopentadienide anion + Hydrogen cation = 1,3-Cyclopentadiene

By formula: C5H5- + H+ = C5H6

Quantity Value Units Method Reference Comment
Δr1481. ± 9.2kJ/molG+TSBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale
Δr1485. ± 12.kJ/molG+TSCumming and Kebarle, 1978gas phase
Δr1495. ± 8.4kJ/molD-EAEngelking and Lineberger, 1977gas phase
Quantity Value Units Method Reference Comment
Δr1455. ± 8.4kJ/molIMREBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale
Δr1459. ± 8.4kJ/molIMRECumming and Kebarle, 1978gas 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.

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]

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]

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]


Notes

Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, References