pyrrolide anion

• Formula: C₄H₄N^-
• Molecular weight: 66.0818
• IUPAC Standard InChI: InChI=1S/C4H4N/c1-2-4-5-3-1/h1-4H/q-1 Copy

  
• IUPAC Standard InChIKey: KFFMWJLUQMFKOH-UHFFFAOYSA-N Copy
• CAS Registry Number: 23303-09-5
• Chemical structure:
  This structure is also available as a 2d Mol file or as a computed 3d SD file
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• Information on this page:
  • Reaction thermochemistry data
  • References
  • Notes
• Other data available:
  • Gas phase ion energetics data
  • Ion clustering data
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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

 +  =

By formula: C₄H₄N^- + H⁺ = C₄H₅N

 +  = ( • )

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

 +  = ( • )

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

 +  = ( • )

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

 +  = ( • )

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

 +  = ( • )

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

 +  = ( • )

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

Free energy of reaction

( • ) +  = ( • 2)

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

( • ) +  = ( • 2)

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

( • ) +  = ( • 2)

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

 +  = ( • )

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

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

Go To: Top, Reaction thermochemistry data, References

• Symbols used in this document:
  

  T	Temperature
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔrS°	Entropy of reaction at standard conditions

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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