Pyrrole

Data at NIST subscription sites:

NIST subscription sites provide data under the NIST Standard Reference Data Program, but require an annual fee to access. The purpose of the fee is to recover costs associated with the development of data collections included in such sites. Your institution may already be a subscriber. Follow the links above to find out more about the data in these sites and their terms of usage.


Gas phase ion energetics 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 evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias
L - Sharon G. Lias

Data compiled as indicated in comments:
B - John E. Bartmess
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

Quantity Value Units Method Reference Comment
IE (evaluated)8.207 ± 0.005eVN/AN/AL
Quantity Value Units Method Reference Comment
Proton affinity (review)209.2kcal/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity201.7kcal/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
8.02PEKlasinc, Sabljic, et al., 1982LBLHLM
8.02PEGalasso, Klasinc, et al., 1981LLK
8.21PEWillett and Baer, 1980LLK
8.4 ± 0.1CEMSTedder and Vidaud, 1980LLK
8.207 ± 0.003PICooper, Williamson, et al., 1980LLK
8.208 ± 0.005PIWilliamson, Compton, et al., 1979LLK
~8.1EIVan Veen, 1976LLK
8.22 ± 0.05EIThorstad and Undheim, 1974LLK
8.40 ± 0.05EILinda, Marino, et al., 1971LLK
8.209PEDerrick, Asbrink, et al., 1971LLK
8.209SDerrick, Asbrink, et al., 1971LLK
8.20 ± 0.01PIPotapov and Yuzhakova, 1970RDSH
8.20 ± 0.01PIPotapov and Bazhenov, 1970RDSH
8.20 ± 0.01PIWatanabe, Nakayama, et al., 1962RDSH
8.23PECradock, Findlay, et al., 1973Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
CH2N+12.40?PIWillett and Baer, 1980LLK
CH2N+12.1 ± 0.2C3H3CEMSTedder and Vidaud, 1980LLK
C2H3+13.60?PIWillett and Baer, 1980LLK
C2H3N+11.75C2H2EISakurai and Jennings, 1981LLK
C2H3N+11.75?PIWillett and Baer, 1980LLK
C3H2N+12.50?PIWillett and Baer, 1980LLK
C3H3+12.60?PIWillett and Baer, 1980LLK
C3H4+12.00?PIWillett and Baer, 1980LLK
C3H4+12.5 ± 0.2CHNCEMSTedder and Vidaud, 1980LLK
C4H4N+12.85HPIWillett and Baer, 1980LLK

De-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; 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

References

Go To: Top, Gas phase ion energetics data, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G., Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update, J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018 . [all data]

Klasinc, Sabljic, et al., 1982
Klasinc, L.; Sabljic, A.; Kluge, G.; Rieger, J.; Scholz, M., Chemistry of excited states. Part 13. Assignment of lowest .PI.-ionizations in photoelectron spectra of thiophen, furan, and pyrrole, J. Chem. Soc. Perkin Trans. 2, 1982, 539. [all data]

Galasso, Klasinc, et al., 1981
Galasso, V.; Klasinc, L.; Sabluic, A.; Trinajstic, N.; Pappalardo, G.C.; Steglich, W., Conformation and photoelectron spectra of 2-(2-Furyl)pyrrole and 2-(2-tThienyl)pyrrole, J. Chem. Soc. Perkin Trans. 2, 1981, 127. [all data]

Willett and Baer, 1980
Willett, G.D.; Baer, T., Thermochemistry and dissociation dynamics of state-selected C4H4X ions. 3. C4H5N+, J. Am. Chem. Soc., 1980, 102, 6774. [all data]

Tedder and Vidaud, 1980
Tedder, J.M.; Vidaud, P.H., Charge exchange mass spectra of thiophene, pyrrole and furan, J. Chem. Soc. Faraday Trans. 2, 1980, 76, 1516. [all data]

Cooper, Williamson, et al., 1980
Cooper, C.D.; Williamson, A.D.; Miller, J.C.; Compton, R.N., Resonantly enhanced multiphoton ionization of pyrrole, N-methyl pyrrole, and furan, J. Chem. Phys., 1980, 73, 1527. [all data]

Williamson, Compton, et al., 1979
Williamson, A.D.; Compton, R.N.; Eland, J.H.D., Accurate photoionization thresholds by multiphoton ionization: Pyrrole, J. Chem. Phys., 1979, 70, 590. [all data]

Van Veen, 1976
Van Veen, E.H., Triplet π-π* transitions in thiophene, furan and pyrrole by low-energy electron-impact spectroscopy, Chem. Phys. Lett., 1976, 41, 535. [all data]

Thorstad and Undheim, 1974
Thorstad, O.; Undheim, K., Mass spectrometry of onium compounds. XXIV. Ionisation potential in structure analysis of pyridodiazo-oxides, Chem. Scr., 1974, 6, 222. [all data]

Linda, Marino, et al., 1971
Linda, P.; Marino, G.; Pignataro, S., A comparison of sensitivities to substituent effects of five- membered heteroaromatic rings in gas phase ionization, J. Chem. Soc. B, 1971, 1585. [all data]

Derrick, Asbrink, et al., 1971
Derrick, P.J.; Asbrink, L.; Edqvist, O.; Jonsson, B.-O.; Lindholm, E., Rydberg series in small molecules. XII. Photoelectron spectroscopy and electronic structure of pyrrole, Intern. J. Mass Spectrom. Ion Phys., 1971, 6, 191. [all data]

Potapov and Yuzhakova, 1970
Potapov, V.K.; Yuzhakova, O.A., Photoionization and electronic structure of pyrrole and its methyl derivatives, Dokl. Akad. Nauk SSSR, 1970, 192, 131, In original 365. [all data]

Potapov and Bazhenov, 1970
Potapov, V.K.; Bazhenov, B.A., The photionization of pyrrole, furan, and thiophene, High Energy Chem., 1970, 505, In original 553. [all data]

Watanabe, Nakayama, et al., 1962
Watanabe, K.; Nakayama, T.; Mottl, J., Ionization potentials of some molecules, J. Quant. Spectry. Radiative Transfer, 1962, 2, 369. [all data]

Cradock, Findlay, et al., 1973
Cradock, S.; Findlay, R.H.; Palmer, M.H., The molecular energy levels of the azoles: A study by photoelectron spectroscopy and ab initio molecular orbital calculations, Tetrahedron, 1973, 29, 2173. [all data]

Sakurai and Jennings, 1981
Sakurai, H.; Jennings, K.R., A study of the structures of decomposing and non-decomposing [C4H5N]+ ions formed from different neutral species, Org. Mass Spectrom., 1981, 16, 393. [all data]

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]


Notes

Go To: Top, Gas phase ion energetics data, References