Pyrrolidine
- Formula: C4H9N
- Molecular weight: 71.1210
- IUPAC Standard InChIKey: RWRDLPDLKQPQOW-UHFFFAOYSA-N
- CAS Registry Number: 123-75-1
- Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
The 3d structure may be viewed using Java or Javascript. - Other names: Azacyclopentane; Azolidine; Butylenimine; Prolamine; Pyrrole, tetrahydro-; Tetrahydropyrrole; Tetramethylenimine; Perhydropyrrole; UN 1922; NSC 62781; Pyrrolidine ring
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | -0.82 ± 0.23 | kcal/mol | Ccb | Hildenbrand, Sinke, et al., 1959 | |
ΔfH°gas | -0.86 ± 0.22 | kcal/mol | Ccb | McCullough, 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 |
---|---|---|---|---|---|
ΔfH°liquid | -9.81 ± 0.20 | kcal/mol | Ccb | Hildenbrand, Sinke, et al., 1959 | ALS |
ΔfH°liquid | -9.84 ± 0.20 | kcal/mol | Ccb | McCullough, Douslin, et al., 1959 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -673.83 ± 0.20 | kcal/mol | Ccb | Hildenbrand, Sinke, et al., 1959 | ALS |
ΔcH°liquid | -673.80 ± 0.18 | kcal/mol | Ccb | McCullough, Douslin, et al., 1959 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°liquid | 48.781 | cal/mol*K | N/A | Hildenbrand, Sinke, et al., 1959 | DH |
S°liquid | 48.760 | cal/mol*K | N/A | McCullough, Douslin, et al., 1959 | DH |
Constant pressure heat capacity of liquid
Cp,liquid (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
38.29 | 298. | Conti, Gianni, et al., 1976 | DH |
37.421 | 298.15 | Hildenbrand, Sinke, et al., 1959 | T = 14 to 312 K.; DH |
37.421 | 298.15 | McCullough, Douslin, et al., 1959 | T = 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+ • ) +
= (C4H10N+ • 2
)
By formula: (C4H10N+ • C4H9N) + C4H9N = (C4H10N+ • 2C4H9N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 15.3 | kcal/mol | PHPMS | Hiraoka, Takimoto, et al., 1987 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 24.3 | cal/mol*K | PHPMS | Hiraoka, Takimoto, et al., 1987 | gas phase; M |
By formula: C4H10N+ + C4H9N = (C4H10N+ • C4H9N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 22.3 | kcal/mol | PHPMS | Hiraoka, Takimoto, et al., 1987 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 23.8 | cal/mol*K | PHPMS | Hiraoka, Takimoto, et al., 1987 | gas phase; M |
By formula: 3H2 + C12H21N3 = 3C4H9N
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -25.0 ± 0.1 | kcal/mol | Chyd | Wiberg, Nakaji, et al., 1993 | liquid 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) | 226.6 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 218.8 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
8.41 | PE | Al-Joboury and Turner, 1964 | RDSH |
8.82 | PE | Gerson, Worley, et al., 1978 | Vertical value; LLK |
8.77 ± 0.02 | PE | Aue, Webb, et al., 1976 | Vertical value; LLK |
8.77 ± 0.05 | PE | Morishima, Yoshikawa, et al., 1975 | Vertical value; LLK |
8.82 ± 0.03 | PE | Colonna, Distefano, et al., 1975 | Vertical value; LLK |
8.77 ± 0.02 | PE | Yoshikawa, Hashimoto, et al., 1974 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
CH2N+ | 13.9 ± 0.2 | ? | EI | Gallegos and Kiser, 1962 | RDSH |
CH4N+ | 12.7 ± 0.2 | ? | EI | Gallegos and Kiser, 1962 | RDSH |
C2H2+ | 17.3 ± 1.0 | ? | EI | Gallegos and Kiser, 1962 | RDSH |
C2H3+ | 16.7 ± 0.3 | ? | EI | Gallegos and Kiser, 1962 | RDSH |
C2H4N+ | 13.0 ± 0.2 | C2H5 | EI | Gallegos and Kiser, 1962 | RDSH |
C2H5N+ | 12.3 ± 0.2 | ? | EI | Gallegos and Kiser, 1962 | RDSH |
C3H3+ | 18.9 ± 0.4 | ? | EI | Gallegos and Kiser, 1962 | RDSH |
C4H8N+ | 11.0 ± 0.2 | H | EI | Gallegos and Kiser, 1962 | RDSH |
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
- Symbols used in this document:
AE Appearance energy Cp,liquid Constant pressure heat capacity of liquid S°liquid Entropy of liquid at standard conditions ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°liquid Enthalpy of formation of liquid 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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