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
Δr359.54 ± 0.25kcal/molD-EAGianola, Ichino, et al., 2004gas phase; B
Δr358.6 ± 2.2kcal/molG+TSBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B
Δr359.6 ± 2.9kcal/molG+TSCumming and Kebarle, 1978gas phase; B
Δr358.6 ± 5.0kcal/molEIAEMuftakhov, Vasil'ev, et al., 1999gas phase; B
Quantity Value Units Method Reference Comment
Δr350.9 ± 2.0kcal/molIMREBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B
Δr351.8 ± 2.0kcal/molIMRECumming and Kebarle, 1978gas phase; B

pyrrolide anion + Water = (pyrrolide anion • Water)

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

Quantity Value Units Method Reference Comment
Δr15.7 ± 1.0kcal/molTDAsMeot-ner, 1988gas phase; B,M
Quantity Value Units Method Reference Comment
Δr23.1cal/mol*KPHPMSMeot-ner, 1988gas phase; M
Quantity Value Units Method Reference Comment
Δr8.8 ± 1.0kcal/molTDAsMeot-ner, 1988gas phase; B

pyrrolide anion + Pyrrole = (pyrrolide anion • Pyrrole)

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

Quantity Value Units Method Reference Comment
Δr26.5 ± 1.0kcal/molTDAsMeot-ner, 1988gas phase; B,M
Quantity Value Units Method Reference Comment
Δr35.2cal/mol*KPHPMSMeot-ner, 1988gas phase; M
Quantity Value Units Method Reference Comment
Δr16.3 ± 1.0kcal/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
Δr18.6 ± 1.0kcal/molTDAsMeot-ner, 1988gas phase; B,M
Quantity Value Units Method Reference Comment
Δr27.5cal/mol*KPHPMSMeot-ner, 1988gas phase; M
Quantity Value Units Method Reference Comment
Δr10.4 ± 1.0kcal/molTDAsMeot-ner, 1988gas phase; B

pyrrolide anion + Acetone = (pyrrolide anion • Acetone)

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

Quantity Value Units Method Reference Comment
Δr13.1 ± 1.0kcal/molTDAsMeot-ner, 1988gas phase; B,M
Quantity Value Units Method Reference Comment
Δr20.5cal/mol*KPHPMSMeot-ner, 1988gas phase; M
Quantity Value Units Method Reference Comment
Δr7.0 ± 1.0kcal/molTDAsMeot-ner, 1988gas phase; B

pyrrolide anion + Acetonitrile = (pyrrolide anion • Acetonitrile)

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

Quantity Value Units Method Reference Comment
Δr15.8 ± 1.0kcal/molTDAsMeot-ner, 1988gas phase; B,M
Quantity Value Units Method Reference Comment
Δr23.4cal/mol*KPHPMSMeot-ner, 1988gas phase; M
Quantity Value Units Method Reference Comment
Δr8.8 ± 1.0kcal/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
Δr27.kcal/molPHPMSMeot-Ner (Mautner), 1988gas phase; M
Quantity Value Units Method Reference Comment
Δr30.cal/mol*KPHPMSMeot-Ner (Mautner), 1988gas phase; M

Free energy of reaction

ΔrG° (kcal/mol) T (K) Method Reference Comment
11.9497.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
Δr12.1kcal/molPHPMSMeot-ner, 1988gas phase; M
Quantity Value Units Method Reference Comment
Δr23.2cal/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
Δr17.1kcal/molPHPMSMeot-ner, 1988gas phase; M
Quantity Value Units Method Reference Comment
Δr31.2cal/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
Δr10.7kcal/molPHPMSMeot-ner, 1988gas phase; M
Quantity Value Units Method Reference Comment
Δr19.0cal/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
Δr26. ± 2.kcal/molPHPMSMeot-Ner (Mautner), 1988gas phase; M
Quantity Value Units Method Reference Comment
Δr31.cal/mol*KPHPMSMeot-Ner (Mautner), 1988gas phase; M

References

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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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