pyrrolide anion


Reaction thermochemistry 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

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Individual Reactions

pyrrolide anion + Hydrogen cation = Pyrrole

By formula: C4H4N- + H+ = C4H5N

Quantity Value Units Method Reference Comment
Δr1504.3 ± 1.0kJ/molD-EAGianola, Ichino, et al., 2004gas phase; B
Δr1500. ± 9.2kJ/molG+TSBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B
Δr1505. ± 12.kJ/molG+TSCumming and Kebarle, 1978gas phase; B
Δr1500. ± 21.kJ/molEIAEMuftakhov, Vasil'ev, et al., 1999gas phase; B
Quantity Value Units Method Reference Comment
Δr1468. ± 8.4kJ/molIMREBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B
Δr1472. ± 8.4kJ/molIMRECumming and Kebarle, 1978gas phase; B

pyrrolide anion + Water = (pyrrolide anion • Water)

By formula: C4H4N- + H2O = (C4H4N- • H2O)

Quantity Value Units Method Reference Comment
Δr65.7 ± 4.2kJ/molTDAsMeot-ner, 1988gas phase; B,M
Quantity Value Units Method Reference Comment
Δr96.7J/mol*KPHPMSMeot-ner, 1988gas phase; M
Quantity Value Units Method Reference Comment
Δr37. ± 4.2kJ/molTDAsMeot-ner, 1988gas phase; B

pyrrolide anion + Pyrrole = (pyrrolide anion • Pyrrole)

By formula: C4H4N- + C4H5N = (C4H4N- • C4H5N)

Quantity Value Units Method Reference Comment
Δr111. ± 4.2kJ/molTDAsMeot-ner, 1988gas phase; B,M
Quantity Value Units Method Reference Comment
Δr147.J/mol*KPHPMSMeot-ner, 1988gas phase; M
Quantity Value Units Method Reference Comment
Δr68.2 ± 4.2kJ/molTDAsMeot-ner, 1988gas phase; B

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

By formula: C4H4N- + CH4O = (C4H4N- • CH4O)

Quantity Value Units Method Reference Comment
Δr77.8 ± 4.2kJ/molTDAsMeot-ner, 1988gas phase; B,M
Quantity Value Units Method Reference Comment
Δr115.J/mol*KPHPMSMeot-ner, 1988gas phase; M
Quantity Value Units Method Reference Comment
Δr43.5 ± 4.2kJ/molTDAsMeot-ner, 1988gas phase; B

pyrrolide anion + Acetone = (pyrrolide anion • Acetone)

By formula: C4H4N- + C3H6O = (C4H4N- • C3H6O)

Quantity Value Units Method Reference Comment
Δr54.8 ± 4.2kJ/molTDAsMeot-ner, 1988gas phase; B,M
Quantity Value Units Method Reference Comment
Δr85.8J/mol*KPHPMSMeot-ner, 1988gas phase; M
Quantity Value Units Method Reference Comment
Δr29. ± 4.2kJ/molTDAsMeot-ner, 1988gas phase; B

pyrrolide anion + Acetonitrile = (pyrrolide anion • Acetonitrile)

By formula: C4H4N- + C2H3N = (C4H4N- • C2H3N)

Quantity Value Units Method Reference Comment
Δr66.1 ± 4.2kJ/molTDAsMeot-ner, 1988gas phase; B,M
Quantity Value Units Method Reference Comment
Δr97.9J/mol*KPHPMSMeot-ner, 1988gas phase; M
Quantity Value Units Method Reference Comment
Δr37. ± 4.2kJ/molTDAsMeot-ner, 1988gas phase; B

pyrrolide anion + Acetamide, N-methyl- = (pyrrolide anion • Acetamide, N-methyl-)

By formula: C4H4N- + C3H7NO = (C4H4N- • C3H7NO)

Quantity Value Units Method Reference Comment
Δr110.kJ/molPHPMSMeot-Ner (Mautner), 1988gas phase; M
Quantity Value Units Method Reference Comment
Δr130.J/mol*KPHPMSMeot-Ner (Mautner), 1988gas phase; M

Free energy of reaction

ΔrG° (kJ/mol) T (K) Method Reference Comment
49.8497.PHPMSMeot-Ner (Mautner), 1988gas phase; M

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

By formula: (C4H4N- • H2O) + H2O = (C4H4N- • 2H2O)

Quantity Value Units Method Reference Comment
Δr50.6kJ/molPHPMSMeot-ner, 1988gas phase; M
Quantity Value Units Method Reference Comment
Δr97.1J/mol*KPHPMSMeot-ner, 1988gas phase; M

(pyrrolide anion • Pyrrole) + Pyrrole = (pyrrolide anion • 2Pyrrole)

By formula: (C4H4N- • C4H5N) + C4H5N = (C4H4N- • 2C4H5N)

Quantity Value Units Method Reference Comment
Δr71.5kJ/molPHPMSMeot-ner, 1988gas phase; M
Quantity Value Units Method Reference Comment
Δr131.J/mol*KPHPMSMeot-ner, 1988gas phase; M

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

By formula: (C4H4N- • C3H6O) + C3H6O = (C4H4N- • 2C3H6O)

Quantity Value Units Method Reference Comment
Δr44.8kJ/molPHPMSMeot-ner, 1988gas phase; M
Quantity Value Units Method Reference Comment
Δr79.5J/mol*KPHPMSMeot-ner, 1988gas phase; M

pyrrolide anion + Formamide, N-methyl- = (pyrrolide anion • Formamide, N-methyl-)

By formula: C4H4N- + C2H5NO = (C4H4N- • C2H5NO)

Quantity Value Units Method Reference Comment
Δr110. ± 8.kJ/molPHPMSMeot-Ner (Mautner), 1988gas phase; M
Quantity Value Units Method Reference Comment
Δr130.J/mol*KPHPMSMeot-Ner (Mautner), 1988gas phase; M

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

Electron affinity of neutral species

EAneutral (eV) Method Reference Comment
2.145 ± 0.010LPESGianola, Ichino, et al., 2004 
2.183 ± 0.095D-EABartmess, Scott, et al., 1979value altered from reference due to change in acidity scale
2.39 ± 0.13PDRichardson, Stephenson, et al., 1975 

Protonation reactions

pyrrolide anion + Hydrogen cation = Pyrrole

By formula: C4H4N- + H+ = C4H5N

Quantity Value Units Method Reference Comment
Δr1504.3 ± 1.0kJ/molD-EAGianola, Ichino, et al., 2004gas phase
Δr1500. ± 9.2kJ/molG+TSBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale
Δr1505. ± 12.kJ/molG+TSCumming and Kebarle, 1978gas phase
Δr1500. ± 21.kJ/molEIAEMuftakhov, Vasil'ev, et al., 1999gas phase
Quantity Value Units Method Reference Comment
Δr1468. ± 8.4kJ/molIMREBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale
Δr1472. ± 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.

Gianola, Ichino, et al., 2004
Gianola, A.J.; Ichino, T.; Hoenigman, R.L.; Kato, S.; Bierbaum, V.M.; Lineberger, W.C., Thermochemistry and electronic structure of the pyrrolyl radical, J. Phys. Chem. A, 2004, 108, 46, 10326-10335, https://doi.org/10.1021/jp047790+ . [all data]

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]

Muftakhov, Vasil'ev, et al., 1999
Muftakhov, M.V.; Vasil'ev, Y.V.; Khatymov, R.V.; Mazunov, V.A.; Takhistov, V.V.; Travkin, O.V.; Yakovleva, E.V., Thermochemistry of negatively charged ions. II. Energetics of formation of negative ions from acridanone and some of its derivatives, Rapid Commun. Mass Spectrom., 1999, 13, 10, 912-923, https://doi.org/10.1002/(SICI)1097-0231(19990530)13:10<912::AID-RCM585>3.0.CO;2-W . [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]

Meot-Ner (Mautner), 1988
Meot-Ner (Mautner), M., Models for Strong Interactions in Proteins and Enzymes. 2. Interactions of Ions with the Peptide Link and Imidazole, J. Am. Chem. Soc., 1988, 110, 10, 3075, https://doi.org/10.1021/ja00218a014 . [all data]

Richardson, Stephenson, et al., 1975
Richardson, J.H.; Stephenson, L.M.; Brauman, J.I., Photodetachment of electrons from large molecular systems. Pyrrolate ion. Electron affinity of C4H4N, J. Am. Chem. Soc., 1975, 97, 1160. [all data]


Notes

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