Pyrrole

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Reaction thermochemistry data

Go To: Top, 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
RCD - Robert C. Dunbar

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

CN- + Pyrrole = (CN- • Pyrrole)

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

Quantity Value Units Method Reference Comment
Δr23.4 ± 1.0kcal/molTDAsMeot-ner, 1988gas phase; B,M
Δr19.5 ± 3.5kcal/molIMRELarson and McMahon, 1987gas phase; B,M
Quantity Value Units Method Reference Comment
Δr27.1cal/mol*KPHPMSMeot-ner, 1988gas phase; M
Δr23.8cal/mol*KN/ALarson and McMahon, 1987gas phase; switching reaction,Thermochemical ladder(CN-)H2O, Entropy change calculated or estimated; Payzant, Yamdagni, et al., 1971; M
Quantity Value Units Method Reference Comment
Δr15.3 ± 1.0kcal/molTDAsMeot-ner, 1988gas phase; B
Δr12.3 ± 2.3kcal/molIMRELarson and McMahon, 1987gas phase; B,M

Fluorine anion + Pyrrole = (Fluorine anion • Pyrrole)

By formula: F- + C4H5N = (F- • C4H5N)

Quantity Value Units Method Reference Comment
Δr34.2 ± 2.0kcal/molIMRELarson and McMahon, 1983gas phase; B,M
Quantity Value Units Method Reference Comment
Δr25.5cal/mol*KN/ALarson and McMahon, 1983gas phase; switching reaction(F-)H2O, Entropy change calculated or estimated; Arshadi, Yamdagni, et al., 1970; M
Quantity Value Units Method Reference Comment
Δr26.6 ± 2.0kcal/molIMRELarson and McMahon, 1983gas phase; B,M

Chlorine anion + Pyrrole = (Chlorine anion • Pyrrole)

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

Quantity Value Units Method Reference Comment
Δr18.8 ± 2.0kcal/molIMRELarson and McMahon, 1984gas phase; B
Quantity Value Units Method Reference Comment
Δr11.8 ± 2.0kcal/molIMRELarson and McMahon, 1984gas phase; B
Δr14.00kcal/molTDEqFrench, Ikuta, et al., 1982gas phase; B

Free energy of reaction

ΔrG° (kcal/mol) T (K) Method Reference Comment
11.6421.PHPMSFrench, Ikuta, et al., 1982gas phase; M

HS- + Pyrrole = (HS- • Pyrrole)

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

Quantity Value Units Method Reference Comment
Δr23.0 ± 1.0kcal/molTDAsMeot-ner, 1988gas phase; B,M
Quantity Value Units Method Reference Comment
Δr24.4cal/mol*KPHPMSMeot-ner, 1988gas phase; M
Quantity Value Units Method Reference Comment
Δr15.7 ± 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, 1988, 2gas phase; B,M
Quantity Value Units Method Reference Comment
Δr35.2cal/mol*KPHPMSMeot-ner, 1988, 2gas phase; M
Quantity Value Units Method Reference Comment
Δr16.3 ± 1.0kcal/molTDAsMeot-ner, 1988, 2gas phase; B

MeCO2 anion + Pyrrole = (MeCO2 anion • Pyrrole)

By formula: C2H3O2- + C4H5N = (C2H3O2- • C4H5N)

Quantity Value Units Method Reference Comment
Δr24.0 ± 1.0kcal/molTDAsMeot-ner, 1988gas phase; B,M
Quantity Value Units Method Reference Comment
Δr25.1cal/mol*KPHPMSMeot-ner, 1988gas phase; M
Quantity Value Units Method Reference Comment
Δr16.5 ± 1.0kcal/molTDAsMeot-ner, 1988gas phase; B

(C4H5N+ • Pyrrole) + Pyrrole = (C4H5N+ • 2Pyrrole)

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

Bond type: Charge transfer bond (positive ion)

Quantity Value Units Method Reference Comment
Δr13.8kcal/molPHPMSHiraoka, Takimoto, et al., 1987gas phase; M
Quantity Value Units Method Reference Comment
Δr29.2cal/mol*KPHPMSHiraoka, Takimoto, et al., 1987gas phase; M

C4H5N+ + Pyrrole = (C4H5N+ • Pyrrole)

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

Bond type: Charge transfer bond (positive ion)

Quantity Value Units Method Reference Comment
Δr16.5kcal/molPHPMSHiraoka, Takimoto, et al., 1987gas phase; M
Quantity Value Units Method Reference Comment
Δr20.3cal/mol*KPHPMSHiraoka, Takimoto, et al., 1987gas phase; M

(C4H6N+ • Pyrrole) + Pyrrole = (C4H6N+ • 2Pyrrole)

By formula: (C4H6N+ • C4H5N) + C4H5N = (C4H6N+ • 2C4H5N)

Quantity Value Units Method Reference Comment
Δr12.3kcal/molPHPMSHiraoka, Takimoto, et al., 1987gas phase; M
Quantity Value Units Method Reference Comment
Δr30.4cal/mol*KPHPMSHiraoka, Takimoto, et al., 1987gas 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, 1988, 2gas phase; M
Quantity Value Units Method Reference Comment
Δr31.2cal/mol*KPHPMSMeot-ner, 1988, 2gas phase; M

C4H6N+ + Pyrrole = (C4H6N+ • Pyrrole)

By formula: C4H6N+ + C4H5N = (C4H6N+ • C4H5N)

Quantity Value Units Method Reference Comment
Δr16.8kcal/molPHPMSHiraoka, Takimoto, et al., 1987gas phase; M
Quantity Value Units Method Reference Comment
Δr24.7cal/mol*KPHPMSHiraoka, Takimoto, et al., 1987gas phase; M

(MeCO2 anion • Pyrrole) + Pyrrole = (MeCO2 anion • 2Pyrrole)

By formula: (C2H3O2- • C4H5N) + C4H5N = (C2H3O2- • 2C4H5N)

Quantity Value Units Method Reference Comment
Δr17.9kcal/molPHPMSMeot-ner, 1988gas phase; M
Quantity Value Units Method Reference Comment
Δr24.2cal/mol*KPHPMSMeot-ner, 1988gas phase; M

CH6N+ + Pyrrole = (CH6N+ • Pyrrole)

By formula: CH6N+ + C4H5N = (CH6N+ • C4H5N)

Quantity Value Units Method Reference Comment
Δr18.6kcal/molPHPMSDeakyne and Meot-Ner (Mautner), 1985gas phase; M
Quantity Value Units Method Reference Comment
Δr21.0cal/mol*KPHPMSDeakyne and Meot-Ner (Mautner), 1985gas phase; M

CH3CONHCH(CH3)COOCH3 + Pyrrole = (CH3CONHCH(CH3)COOCH3 • Pyrrole)

By formula: C6H11NO3 + C4H5N = (C6H11NO3 • C4H5N)

Quantity Value Units Method Reference Comment
Δr24.0kcal/molPHPMSMeot-Ner (Mautner), 1988gas phase; M
Quantity Value Units Method Reference Comment
Δr32.1cal/mol*KPHPMSMeot-Ner (Mautner), 1988gas phase; M

(Iron ion (1+) • Pyrrole) + Pyrrole = (Iron ion (1+) • 2Pyrrole)

By formula: (Fe+ • C4H5N) + C4H5N = (Fe+ • 2C4H5N)

Quantity Value Units Method Reference Comment
Δr41.6kcal/molRAKGapeev and Yang, 2000RCD

(Chromium ion (1+) • Pyrrole) + Pyrrole = (Chromium ion (1+) • 2Pyrrole)

By formula: (Cr+ • C4H5N) + C4H5N = (Cr+ • 2C4H5N)

Quantity Value Units Method Reference Comment
Δr34.9kcal/molRAKGapeev and Yang, 2000RCD

(Manganese ion (1+) • Pyrrole) + Pyrrole = (Manganese ion (1+) • 2Pyrrole)

By formula: (Mn+ • C4H5N) + C4H5N = (Mn+ • 2C4H5N)

Quantity Value Units Method Reference Comment
Δr27.0kcal/molRAKGapeev and Yang, 2000RCD

(Nickel ion (1+) • Pyrrole) + Pyrrole = (Nickel ion (1+) • 2Pyrrole)

By formula: (Ni+ • C4H5N) + C4H5N = (Ni+ • 2C4H5N)

Quantity Value Units Method Reference Comment
Δr47.0kcal/molRAKGapeev and Yang, 2000RCD

(Cobalt ion (1+) • Pyrrole) + Pyrrole = (Cobalt ion (1+) • 2Pyrrole)

By formula: (Co+ • C4H5N) + C4H5N = (Co+ • 2C4H5N)

Quantity Value Units Method Reference Comment
Δr46.4kcal/molRAKGapeev and Yang, 2000RCD

(Copper ion (1+) • Pyrrole) + Pyrrole = (Copper ion (1+) • 2Pyrrole)

By formula: (Cu+ • C4H5N) + C4H5N = (Cu+ • 2C4H5N)

Quantity Value Units Method Reference Comment
Δr44.0kcal/molRAKGapeev and Yang, 2000RCD

Lithium ion (1+) + Pyrrole = (Lithium ion (1+) • Pyrrole)

By formula: Li+ + C4H5N = (Li+ • C4H5N)

Quantity Value Units Method Reference Comment
Δr42.3 ± 4.0kcal/molCIDTHuang and Rodgers, 2002RCD

Sodium ion (1+) + Pyrrole = (Sodium ion (1+) • Pyrrole)

By formula: Na+ + C4H5N = (Na+ • C4H5N)

Quantity Value Units Method Reference Comment
Δr24.3 ± 1.1kcal/molCIDTHuang and Rodgers, 2002RCD

Potassium ion (1+) + Pyrrole = (Potassium ion (1+) • Pyrrole)

By formula: K+ + C4H5N = (K+ • C4H5N)

Quantity Value Units Method Reference Comment
Δr20.0 ± 1.0kcal/molCIDTHuang and Rodgers, 2002RCD

Vanadium ion (1+) + Pyrrole = (Vanadium ion (1+) • Pyrrole)

By formula: V+ + C4H5N = (V+ • C4H5N)

Quantity Value Units Method Reference Comment
Δr>41.kcal/molRAKGapeev and Yang, 2000RCD

Nickel ion (1+) + Pyrrole = (Nickel ion (1+) • Pyrrole)

By formula: Ni+ + C4H5N = (Ni+ • C4H5N)

Quantity Value Units Method Reference Comment
Δr>68.kcal/molRAKGapeev and Yang, 2000RCD

Tungsten ion (1+) + Pyrrole = (Tungsten ion (1+) • Pyrrole)

By formula: W+ + C4H5N = (W+ • C4H5N)

Quantity Value Units Method Reference Comment
Δr>50.kcal/molRAKGapeev and Yang, 2000RCD

Cobalt ion (1+) + Pyrrole = (Cobalt ion (1+) • Pyrrole)

By formula: Co+ + C4H5N = (Co+ • C4H5N)

Quantity Value Units Method Reference Comment
Δr>66.kcal/molRAKGapeev and Yang, 2000RCD

Molybdenum ion (1+) + Pyrrole = (Molybdenum ion (1+) • Pyrrole)

By formula: Mo+ + C4H5N = (Mo+ • C4H5N)

Quantity Value Units Method Reference Comment
Δr>69.kcal/molRAKGapeev and Yang, 2000RCD

Iron ion (1+) + Pyrrole = (Iron ion (1+) • Pyrrole)

By formula: Fe+ + C4H5N = (Fe+ • C4H5N)

Quantity Value Units Method Reference Comment
Δr54.0kcal/molRAKGapeev and Yang, 2000RCD

Chromium ion (1+) + Pyrrole = (Chromium ion (1+) • Pyrrole)

By formula: Cr+ + C4H5N = (Cr+ • C4H5N)

Quantity Value Units Method Reference Comment
Δr42.5kcal/molRAKGapeev and Yang, 2000RCD

Manganese ion (1+) + Pyrrole = (Manganese ion (1+) • Pyrrole)

By formula: Mn+ + C4H5N = (Mn+ • C4H5N)

Quantity Value Units Method Reference Comment
Δr42.3kcal/molRAKGapeev and Yang, 2000RCD

Magnesium ion (1+) + Pyrrole = (Magnesium ion (1+) • Pyrrole)

By formula: Mg+ + C4H5N = (Mg+ • C4H5N)

Quantity Value Units Method Reference Comment
Δr44.0kcal/molRAKGapeev and Yang, 2000RCD

Aluminum ion (1+) + Pyrrole = (Aluminum ion (1+) • Pyrrole)

By formula: Al+ + C4H5N = (Al+ • C4H5N)

Quantity Value Units Method Reference Comment
Δr44.0kcal/molRAKGapeev and Yang, 2000RCD

Copper ion (1+) + Pyrrole = (Copper ion (1+) • Pyrrole)

By formula: Cu+ + C4H5N = (Cu+ • C4H5N)

Quantity Value Units Method Reference Comment
Δr59.0kcal/molRAKGapeev and Yang, 2000RCD

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., Ionic Hydrogen Bond and Ion Solvation. 6. Interaction Energies of the Acetate Ion with Organic Molecules. Comparison of CH3COO- with Cl-, CN-, and SH-, J. Am. Chem. Soc., 1988, 110, 12, 3854, https://doi.org/10.1021/ja00220a022 . [all data]

Larson and McMahon, 1987
Larson, J.W.; McMahon, T.B., Hydrogen bonding in gas phase anions. The energetics of interaction between cyanide ion and bronsted acids, J. Am. Chem. Soc., 1987, 109, 6230. [all data]

Payzant, Yamdagni, et al., 1971
Payzant, J.D.; Yamdagni, R.; Kebarle, P., Hydration of CN-, NO2-, NO3-, and HO- in the gas phase, Can. J. Chem., 1971, 49, 3308. [all data]

Larson and McMahon, 1983
Larson, J.W.; McMahon, T.B., Strong hydrogen bonding in gas-phase anions. An ion cyclotron resonance determination of fluoride binding energetics to bronsted acids from gas-phase fluoride exchange equilibria measurements, J. Am. Chem. Soc., 1983, 105, 2944. [all data]

Arshadi, Yamdagni, et al., 1970
Arshadi, M.; Yamdagni, R.; Kebarle, P., Hydration of Halide Negative Ions in the Gas Phase. II. Comparison of Hydration Energies for the Alkali Positive and Halide Negative Ions, J. Phys. Chem., 1970, 74, 7, 1475, https://doi.org/10.1021/j100702a014 . [all data]

Larson and McMahon, 1984
Larson, J.W.; McMahon, T.B., Hydrogen bonding in gas phase anions. An experimental investigation of the interaction between chloride ion and bronsted acids from ICR chloride exchange equilibria, J. Am. Chem. Soc., 1984, 106, 517. [all data]

French, Ikuta, et al., 1982
French, M.A.; Ikuta, S.; Kebarle, P., Hydrogen bonding of O-H and C-H hydrogen donors to Cl-. Results from mass spectrometric measurement of the ion-molecule equilibria RH + Cl- = RHCl-, Can. J. Chem., 1982, 60, 1907. [all data]

Meot-ner, 1988, 2
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]

Hiraoka, Takimoto, et al., 1987
Hiraoka, K.; Takimoto, H.; Yamabe, S., Stabilities and Structures in Cluster Ions of Five-Membered Heterocyclic Compounds Containing O, N and S Atoms, J. Am. Chem. Soc., 1987, 109, 24, 7346, https://doi.org/10.1021/ja00258a018 . [all data]

Deakyne and Meot-Ner (Mautner), 1985
Deakyne, C.A.; Meot-Ner (Mautner), M., Unconventional Ionic Hydrogen Bonds. 2. NH+ pi. Complexes of Onium Ions with Olefins and Benzene Derivatives, J. Am. Chem. Soc., 1985, 107, 2, 474, https://doi.org/10.1021/ja00288a034 . [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]

Gapeev and Yang, 2000
Gapeev, A.; Yang, C.-N., Binding Energies of Gas-Phase Ions with Pyrrole. Experimental and Quantum Chemical Results, J. Phys. Chem. A, 2000, 104, 14, 3246, https://doi.org/10.1021/jp992627d . [all data]

Huang and Rodgers, 2002
Huang, H.; Rodgers, M.T., Sigma versus Pi interactions in alkali metal ion binding to azoles: Threshold collision-induced dissociation and ab initio theory studies, J. Phys. Chem. A, 2002, 106, 16, 4277, https://doi.org/10.1021/jp013630b . [all data]


Notes

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