Home Symbol which looks like a small house Up Solid circle with an upward pointer in it

cyclopentadienide anion


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

cyclopentadienide anion + Hydrogen cation = 1,3-Cyclopentadiene

By formula: C5H5- + H+ = C5H6

Quantity Value Units Method Reference Comment
Deltar1481. ± 9.2kJ/molG+TSBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B
Deltar1485. ± 12.kJ/molG+TSCumming and Kebarle, 1978gas phase; B
Deltar1495. ± 8.4kJ/molD-EAEngelking and Lineberger, 1977gas phase; B
Quantity Value Units Method Reference Comment
Deltar1455. ± 8.4kJ/molIMREBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B
Deltar1459. ± 8.4kJ/molIMRECumming and Kebarle, 1978gas phase; B

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

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

Quantity Value Units Method Reference Comment
Deltar<36.0kJ/molIMRBMeot-ner, 1988gas phase; B,M
Quantity Value Units Method Reference Comment
Deltar84.J/mol*KN/AMeot-ner, 1988gas phase; Entropy change calculated or estimated, DG<, «DELTA»rH<; M
Quantity Value Units Method Reference Comment
Deltar<11. ± 4.2kJ/molIMRBMeot-ner, 1988gas phase; B

Free energy of reaction

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

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

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

Quantity Value Units Method Reference Comment
Deltar42.7kJ/molPHPMSMeot-ner, 1988gas phase; Entropy change calculated or estimated, «DELTA»rH<, CD3CN; M
Quantity Value Units Method Reference Comment
Deltar92.J/mol*KN/AMeot-ner, 1988gas phase; Entropy change calculated or estimated, «DELTA»rH<, CD3CN; M

Free energy of reaction

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

cyclopentadienide anion + Water = (cyclopentadienide anion bullet Water)

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

Quantity Value Units Method Reference Comment
Deltar46.0 ± 4.2kJ/molTDAsMeot-ner, 1988gas phase; B,M
Quantity Value Units Method Reference Comment
Deltar67.4J/mol*KPHPMSMeot-ner, 1988gas phase; M
Quantity Value Units Method Reference Comment
Deltar26. ± 4.2kJ/molTDAsMeot-ner, 1988gas phase; B

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

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

Quantity Value Units Method Reference Comment
Deltar80.3 ± 4.2kJ/molTDAsMeot-ner, 1988gas phase; B,M
Quantity Value Units Method Reference Comment
Deltar125.J/mol*KPHPMSMeot-ner, 1988gas phase; M
Quantity Value Units Method Reference Comment
Deltar43.1 ± 4.2kJ/molTDAsMeot-ner, 1988gas phase; B

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

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

Quantity Value Units Method Reference Comment
Deltar86.2 ± 4.2kJ/molTDAsMeot-ner, 1988gas phase; B,M
Quantity Value Units Method Reference Comment
Deltar102.J/mol*KPHPMSMeot-ner, 1988gas phase; M
Quantity Value Units Method Reference Comment
Deltar55.6 ± 4.2kJ/molTDAsMeot-ner, 1988gas phase; B

cyclopentadienide anion + Acetone = (cyclopentadienide anion bullet Acetone)

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

Quantity Value Units Method Reference Comment
Deltar56.5 ± 4.2kJ/molTDAsMeot-ner, 1988gas phase; B,M
Quantity Value Units Method Reference Comment
Deltar91.2J/mol*KPHPMSMeot-ner, 1988gas phase; M
Quantity Value Units Method Reference Comment
Deltar29. ± 4.2kJ/molTDAsMeot-ner, 1988gas phase; B

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

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

Quantity Value Units Method Reference Comment
Deltar71.1 ± 4.2kJ/molTDAsMeot-ner, 1988gas phase; B,M
Quantity Value Units Method Reference Comment
Deltar134.J/mol*KPHPMSMeot-ner, 1988gas phase; M
Quantity Value Units Method Reference Comment
Deltar31. ± 4.2kJ/molTDAsMeot-ner, 1988gas phase; B

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

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

Quantity Value Units Method Reference Comment
Deltar54.8kJ/molPHPMSMeot-ner, 1988gas phase; CD3CN; M
Quantity Value Units Method Reference Comment
Deltar95.4J/mol*KPHPMSMeot-ner, 1988gas phase; CD3CN; M

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

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

Quantity Value Units Method Reference Comment
Deltar55.2 ± 4.2kJ/molTDAsMeot-ner, 1988gas phase; B
Quantity Value Units Method Reference Comment
Deltar29. ± 4.2kJ/molTDAsMeot-ner, 1988gas phase; B

cyclopentadienide anion + Acetonitrile = (cyclopentadienide anion bullet Acetonitrile)

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

Quantity Value Units Method Reference Comment
Deltar64.9 ± 4.2kJ/molTDAsMeot-ner, 1988gas phase; B
Quantity Value Units Method Reference Comment
Deltar36. ± 4.2kJ/molTDAsMeot-ner, 1988gas phase; B

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

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

Quantity Value Units Method Reference Comment
Deltar41.8kJ/molPHPMSMeot-ner, 1988gas phase; M
Quantity Value Units Method Reference Comment
Deltar72.8J/mol*KPHPMSMeot-ner, 1988gas phase; M

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

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

Quantity Value Units Method Reference Comment
Deltar41.kJ/molPHPMSMeot-ner, 1988gas phase; M
Quantity Value Units Method Reference Comment
Deltar68.6J/mol*KPHPMSMeot-ner, 1988gas phase; M

cyclopentadienide anion + C2D3N = (cyclopentadienide anion bullet C2D3N)

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

Quantity Value Units Method Reference Comment
Deltar64.9kJ/molPHPMSMeot-ner, 1988gas phase; M
Quantity Value Units Method Reference Comment
Deltar95.4J/mol*KPHPMSMeot-ner, 1988gas phase; M

cyclopentadienide anion + CCoO = C6H5CoO-

By formula: C5H5- + CCoO = C6H5CoO-

Quantity Value Units Method Reference Comment
Deltar42.7 ± 3.3kJ/molN/ASunderlin and Squires, 1999gas phase; B

cyclopentadienide anion + cobalt = C5H5Co-

By formula: C5H5- + Co = C5H5Co-

Quantity Value Units Method Reference Comment
Deltar29.3 ± 2.5kJ/molN/ASunderlin and Squires, 1999gas phase; B

Gas phase ion energetics data

Go To: Top, Reaction thermochemistry 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 by: John E. Bartmess

Protonation reactions

cyclopentadienide anion + Hydrogen cation = 1,3-Cyclopentadiene

By formula: C5H5- + H+ = C5H6

Quantity Value Units Method Reference Comment
Deltar1481. ± 9.2kJ/molG+TSBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale
Deltar1485. ± 12.kJ/molG+TSCumming and Kebarle, 1978gas phase
Deltar1495. ± 8.4kJ/molD-EAEngelking and Lineberger, 1977gas phase
Quantity Value Units Method Reference Comment
Deltar1455. ± 8.4kJ/molIMREBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale
Deltar1459. ± 8.4kJ/molIMRECumming and Kebarle, 1978gas phase

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:
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

cyclopentadienide anion + CCoO = C6H5CoO-

By formula: C5H5- + CCoO = C6H5CoO-

Quantity Value Units Method Reference Comment
Deltar42.7 ± 3.3kJ/molN/ASunderlin and Squires, 1999gas phase; B

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

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

Quantity Value Units Method Reference Comment
Deltar55.2 ± 4.2kJ/molTDAsMeot-ner, 1988gas phase; B
Quantity Value Units Method Reference Comment
Deltar29. ± 4.2kJ/molTDAsMeot-ner, 1988gas phase; B

cyclopentadienide anion + C2D3N = (cyclopentadienide anion bullet C2D3N)

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

Quantity Value Units Method Reference Comment
Deltar64.9kJ/molPHPMSMeot-ner, 1988gas phase; M
Quantity Value Units Method Reference Comment
Deltar95.4J/mol*KPHPMSMeot-ner, 1988gas phase; M

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

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

Quantity Value Units Method Reference Comment
Deltar54.8kJ/molPHPMSMeot-ner, 1988gas phase; CD3CN; M
Quantity Value Units Method Reference Comment
Deltar95.4J/mol*KPHPMSMeot-ner, 1988gas phase; CD3CN; M

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

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

Quantity Value Units Method Reference Comment
Deltar42.7kJ/molPHPMSMeot-ner, 1988gas phase; Entropy change calculated or estimated, «DELTA»rH<, CD3CN; M
Quantity Value Units Method Reference Comment
Deltar92.J/mol*KN/AMeot-ner, 1988gas phase; Entropy change calculated or estimated, «DELTA»rH<, CD3CN; M

Free energy of reaction

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

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

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

Quantity Value Units Method Reference Comment
Deltar86.2 ± 4.2kJ/molTDAsMeot-ner, 1988gas phase; B,M
Quantity Value Units Method Reference Comment
Deltar102.J/mol*KPHPMSMeot-ner, 1988gas phase; M
Quantity Value Units Method Reference Comment
Deltar55.6 ± 4.2kJ/molTDAsMeot-ner, 1988gas phase; B

cyclopentadienide anion + Acetonitrile = (cyclopentadienide anion bullet Acetonitrile)

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

Quantity Value Units Method Reference Comment
Deltar64.9 ± 4.2kJ/molTDAsMeot-ner, 1988gas phase; B
Quantity Value Units Method Reference Comment
Deltar36. ± 4.2kJ/molTDAsMeot-ner, 1988gas phase; B

cyclopentadienide anion + Acetone = (cyclopentadienide anion bullet Acetone)

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

Quantity Value Units Method Reference Comment
Deltar56.5 ± 4.2kJ/molTDAsMeot-ner, 1988gas phase; B,M
Quantity Value Units Method Reference Comment
Deltar91.2J/mol*KPHPMSMeot-ner, 1988gas phase; M
Quantity Value Units Method Reference Comment
Deltar29. ± 4.2kJ/molTDAsMeot-ner, 1988gas phase; B

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

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

Quantity Value Units Method Reference Comment
Deltar41.kJ/molPHPMSMeot-ner, 1988gas phase; M
Quantity Value Units Method Reference Comment
Deltar68.6J/mol*KPHPMSMeot-ner, 1988gas phase; M

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

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

Quantity Value Units Method Reference Comment
Deltar71.1 ± 4.2kJ/molTDAsMeot-ner, 1988gas phase; B,M
Quantity Value Units Method Reference Comment
Deltar134.J/mol*KPHPMSMeot-ner, 1988gas phase; M
Quantity Value Units Method Reference Comment
Deltar31. ± 4.2kJ/molTDAsMeot-ner, 1988gas phase; B

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

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

Quantity Value Units Method Reference Comment
Deltar<36.0kJ/molIMRBMeot-ner, 1988gas phase; B,M
Quantity Value Units Method Reference Comment
Deltar84.J/mol*KN/AMeot-ner, 1988gas phase; Entropy change calculated or estimated, DG<, «DELTA»rH<; M
Quantity Value Units Method Reference Comment
Deltar<11. ± 4.2kJ/molIMRBMeot-ner, 1988gas phase; B

Free energy of reaction

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

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

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

Quantity Value Units Method Reference Comment
Deltar80.3 ± 4.2kJ/molTDAsMeot-ner, 1988gas phase; B,M
Quantity Value Units Method Reference Comment
Deltar125.J/mol*KPHPMSMeot-ner, 1988gas phase; M
Quantity Value Units Method Reference Comment
Deltar43.1 ± 4.2kJ/molTDAsMeot-ner, 1988gas phase; B

cyclopentadienide anion + cobalt = C5H5Co-

By formula: C5H5- + Co = C5H5Co-

Quantity Value Units Method Reference Comment
Deltar29.3 ± 2.5kJ/molN/ASunderlin and Squires, 1999gas phase; B

cyclopentadienide anion + Water = (cyclopentadienide anion bullet Water)

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

Quantity Value Units Method Reference Comment
Deltar46.0 ± 4.2kJ/molTDAsMeot-ner, 1988gas phase; B,M
Quantity Value Units Method Reference Comment
Deltar67.4J/mol*KPHPMSMeot-ner, 1988gas phase; M
Quantity Value Units Method Reference Comment
Deltar26. ± 4.2kJ/molTDAsMeot-ner, 1988gas phase; B

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

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

Quantity Value Units Method Reference Comment
Deltar41.8kJ/molPHPMSMeot-ner, 1988gas phase; M
Quantity Value Units Method Reference Comment
Deltar72.8J/mol*KPHPMSMeot-ner, 1988gas phase; M

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.

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, Ion clustering data, References