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

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

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

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

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 + 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 + 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

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 • 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 + 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 + 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 • 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 + 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 • 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

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.

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, Ion clustering data, References