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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
Deltar1504.3 ± 1.0kJ/molD-EAGianola, Ichino, et al., 2004gas phase; B
Deltar1500. ± 9.2kJ/molG+TSBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B
Deltar1505. ± 12.kJ/molG+TSCumming and Kebarle, 1978gas phase; B
Deltar1500. ± 21.kJ/molEIAEMuftakhov, Vasil'ev, et al., 1999gas phase; B
Quantity Value Units Method Reference Comment
Deltar1468. ± 8.4kJ/molIMREBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B
Deltar1472. ± 8.4kJ/molIMRECumming and Kebarle, 1978gas phase; B

pyrrolide anion + Water = (pyrrolide anion bullet Water)

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

Quantity Value Units Method Reference Comment
Deltar65.7 ± 4.2kJ/molTDAsMeot-ner, 1988gas phase; B,M
Quantity Value Units Method Reference Comment
Deltar96.7J/mol*KPHPMSMeot-ner, 1988gas phase; M
Quantity Value Units Method Reference Comment
Deltar37. ± 4.2kJ/molTDAsMeot-ner, 1988gas phase; B

pyrrolide anion + Pyrrole = (pyrrolide anion bullet Pyrrole)

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

Quantity Value Units Method Reference Comment
Deltar111. ± 4.2kJ/molTDAsMeot-ner, 1988gas phase; B,M
Quantity Value Units Method Reference Comment
Deltar147.J/mol*KPHPMSMeot-ner, 1988gas phase; M
Quantity Value Units Method Reference Comment
Deltar68.2 ± 4.2kJ/molTDAsMeot-ner, 1988gas phase; B

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

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

Quantity Value Units Method Reference Comment
Deltar77.8 ± 4.2kJ/molTDAsMeot-ner, 1988gas phase; B,M
Quantity Value Units Method Reference Comment
Deltar115.J/mol*KPHPMSMeot-ner, 1988gas phase; M
Quantity Value Units Method Reference Comment
Deltar43.5 ± 4.2kJ/molTDAsMeot-ner, 1988gas phase; B

pyrrolide anion + Acetone = (pyrrolide anion bullet Acetone)

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

Quantity Value Units Method Reference Comment
Deltar54.8 ± 4.2kJ/molTDAsMeot-ner, 1988gas phase; B,M
Quantity Value Units Method Reference Comment
Deltar85.8J/mol*KPHPMSMeot-ner, 1988gas phase; M
Quantity Value Units Method Reference Comment
Deltar29. ± 4.2kJ/molTDAsMeot-ner, 1988gas phase; B

pyrrolide anion + Acetonitrile = (pyrrolide anion bullet Acetonitrile)

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

Quantity Value Units Method Reference Comment
Deltar66.1 ± 4.2kJ/molTDAsMeot-ner, 1988gas phase; B,M
Quantity Value Units Method Reference Comment
Deltar97.9J/mol*KPHPMSMeot-ner, 1988gas phase; M
Quantity Value Units Method Reference Comment
Deltar37. ± 4.2kJ/molTDAsMeot-ner, 1988gas phase; B

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

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

Quantity Value Units Method Reference Comment
Deltar110.kJ/molPHPMSMeot-Ner (Mautner), 1988gas phase; M
Quantity Value Units Method Reference Comment
Deltar130.J/mol*KPHPMSMeot-Ner (Mautner), 1988gas phase; M

Free energy of reaction

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

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

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

Quantity Value Units Method Reference Comment
Deltar50.6kJ/molPHPMSMeot-ner, 1988gas phase; M
Quantity Value Units Method Reference Comment
Deltar97.1J/mol*KPHPMSMeot-ner, 1988gas phase; M

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

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

Quantity Value Units Method Reference Comment
Deltar71.5kJ/molPHPMSMeot-ner, 1988gas phase; M
Quantity Value Units Method Reference Comment
Deltar131.J/mol*KPHPMSMeot-ner, 1988gas phase; M

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

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

Quantity Value Units Method Reference Comment
Deltar44.8kJ/molPHPMSMeot-ner, 1988gas phase; M
Quantity Value Units Method Reference Comment
Deltar79.5J/mol*KPHPMSMeot-ner, 1988gas phase; M

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

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

Quantity Value Units Method Reference Comment
Deltar110. ± 8.kJ/molPHPMSMeot-Ner (Mautner), 1988gas phase; M
Quantity Value Units Method Reference Comment
Deltar130.J/mol*KPHPMSMeot-Ner (Mautner), 1988gas phase; M

References

Go To: Top, Reaction thermochemistry 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]


Notes

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