Pyrrolidine

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Gas phase 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity Value Units Method Reference Comment
Δfgas-0.82 ± 0.23kcal/molCcbHildenbrand, Sinke, et al., 1959 
Δfgas-0.86 ± 0.22kcal/molCcbMcCullough, Douslin, et al., 1959 

Condensed phase 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:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity Value Units Method Reference Comment
Δfliquid-9.81 ± 0.20kcal/molCcbHildenbrand, Sinke, et al., 1959ALS
Δfliquid-9.84 ± 0.20kcal/molCcbMcCullough, Douslin, et al., 1959ALS
Quantity Value Units Method Reference Comment
Δcliquid-673.83 ± 0.20kcal/molCcbHildenbrand, Sinke, et al., 1959ALS
Δcliquid-673.80 ± 0.18kcal/molCcbMcCullough, Douslin, et al., 1959ALS
Quantity Value Units Method Reference Comment
liquid48.781cal/mol*KN/AHildenbrand, Sinke, et al., 1959DH
liquid48.760cal/mol*KN/AMcCullough, Douslin, et al., 1959DH

Constant pressure heat capacity of liquid

Cp,liquid (cal/mol*K) Temperature (K) Reference Comment
38.29298.Conti, Gianni, et al., 1976DH
37.421298.15Hildenbrand, Sinke, et al., 1959T = 14 to 312 K.; DH
37.421298.15McCullough, Douslin, et al., 1959T = 13 to 350 K.; DH

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:
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

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

(C4H10N+ • Pyrrolidine) + Pyrrolidine = (C4H10N+ • 2Pyrrolidine)

By formula: (C4H10N+ • C4H9N) + C4H9N = (C4H10N+ • 2C4H9N)

Quantity Value Units Method Reference Comment
Δr15.3kcal/molPHPMSHiraoka, Takimoto, et al., 1987gas phase; M
Quantity Value Units Method Reference Comment
Δr24.3cal/mol*KPHPMSHiraoka, Takimoto, et al., 1987gas phase; M

C4H10N+ + Pyrrolidine = (C4H10N+ • Pyrrolidine)

By formula: C4H10N+ + C4H9N = (C4H10N+ • C4H9N)

Quantity Value Units Method Reference Comment
Δr22.3kcal/molPHPMSHiraoka, Takimoto, et al., 1987gas phase; M
Quantity Value Units Method Reference Comment
Δr23.8cal/mol*KPHPMSHiraoka, Takimoto, et al., 1987gas phase; M

3Hydrogen + Dodecahydrotripyrrolo[1,2-a:1',2'-c:1",2"-e][1,3,5]triazine = 3Pyrrolidine

By formula: 3H2 + C12H21N3 = 3C4H9N

Quantity Value Units Method Reference Comment
Δr-25.0 ± 0.1kcal/molChydWiberg, Nakaji, et al., 1993liquid phase; solvent: Acetic acid; ALS

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 evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias

Data compiled as indicated in comments:
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
Proton affinity (review)226.6kcal/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity218.8kcal/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
8.41PEAl-Joboury and Turner, 1964RDSH
8.82PEGerson, Worley, et al., 1978Vertical value; LLK
8.77 ± 0.02PEAue, Webb, et al., 1976Vertical value; LLK
8.77 ± 0.05PEMorishima, Yoshikawa, et al., 1975Vertical value; LLK
8.82 ± 0.03PEColonna, Distefano, et al., 1975Vertical value; LLK
8.77 ± 0.02PEYoshikawa, Hashimoto, et al., 1974Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
CH2N+13.9 ± 0.2?EIGallegos and Kiser, 1962RDSH
CH4N+12.7 ± 0.2?EIGallegos and Kiser, 1962RDSH
C2H2+17.3 ± 1.0?EIGallegos and Kiser, 1962RDSH
C2H3+16.7 ± 0.3?EIGallegos and Kiser, 1962RDSH
C2H4N+13.0 ± 0.2C2H5EIGallegos and Kiser, 1962RDSH
C2H5N+12.3 ± 0.2?EIGallegos and Kiser, 1962RDSH
C3H3+18.9 ± 0.4?EIGallegos and Kiser, 1962RDSH
C4H8N+11.0 ± 0.2HEIGallegos and Kiser, 1962RDSH

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, 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.

Hildenbrand, Sinke, et al., 1959
Hildenbrand, D.L.; Sinke, G.C.; McDonald, R.A.; Kramer, W.R.; Stull, D.R., Thermodynamic and spectroscopic study of pyrrolidine. I. Thermodynamic properties in the solid, liquid, and vapor states, J. Chem. Phys., 1959, 31, 650-654. [all data]

McCullough, Douslin, et al., 1959
McCullough, J.P.; Douslin, D.R.; Hubbard, W.N.; Todd, S.S.; Messerly, J.F.; Hossenlopp, I.A.; Frow, F.R.; Dawson, J.P.; Waddington, G., Pyrrolidine: Chemical thermodynamic properties between 0 and 1500°K; effect of pseudorotation; and an unusual thermal anomaly in the liquid state, J. Am. Chem. Soc., 1959, 81, 5884-5890. [all data]

Conti, Gianni, et al., 1976
Conti, G.; Gianni, P.; Matteoli, E.; Mengheri, M., Capacita termiche molari di alcuni composti organici mono- e bifunzionali nel liquido puro e in soluzione acquosa a 25C, Chim. Ind. (Milan), 1976, 58, 225. [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]

Wiberg, Nakaji, et al., 1993
Wiberg, K.B.; Nakaji, D.Y.; Morgan, K.M., Heat of hydrogenation of a cis imine. An experimental and theoretical study, J. Am. Chem. Soc., 1993, 115, 3527-3532. [all data]

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]

Al-Joboury and Turner, 1964
Al-Joboury, M.I.; Turner, D.W., Molecular photoelectron spectroscopy. Part II. A summary of ionization potentials, J. Chem. Soc., 1964, 4434. [all data]

Gerson, Worley, et al., 1978
Gerson, S.H.; Worley, S.D.; Bodor, N.; Kaminski, J.J.; Flechtner, T.W., The photoelectron spectra of some heterocyclic compounds which contain N, O, Cl, and Br, J. Electron Spectrosc. Relat. Phenom., 1978, 13, 421. [all data]

Aue, Webb, et al., 1976
Aue, D.H.; Webb, H.M.; Bowers, M.T., Quantitative proton affinities, ionization potentials, and hydrogen affinities of alkylamines, J. Am. Chem. Soc., 1976, 98, 311. [all data]

Morishima, Yoshikawa, et al., 1975
Morishima, I.; Yoshikawa, K.; Hashimoto, M.; Bekki, K., Homoallylic interaction between the nitrogen lone pair and the nonadjacent π bond in cyclic and bicyclic amines. I. Photoelectron spectroscopic study, J. Am. Chem. Soc., 1975, 97, 4283. [all data]

Colonna, Distefano, et al., 1975
Colonna, F.P.; Distefano, G.; Pignataro, S.; Pitacco, G.; Valentin, E., Ionization energies of some amines and enamines and an estimation of their relative basicity in gaseous phase, J. Chem. Soc. Faraday Trans. 2, 1975, 71, 1572. [all data]

Yoshikawa, Hashimoto, et al., 1974
Yoshikawa, K.; Hashimoto, M.; Morishima, I., Photoelectron spectroscopic study of cyclic amines. The relation between ionization potentials, basicities, and s character of the nitrogen lone pair electrons, J. Am. Chem. Soc., 1974, 96, 288. [all data]

Gallegos and Kiser, 1962
Gallegos, E.J.; Kiser, R.W., Electron impact spectroscopy of the four- and five-membered, saturated heterocyclic compounds containing nitrogen, oxygen and sulfur, J. Phys. Chem., 1962, 66, 136. [all data]


Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, References