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, Phase change data, Reaction thermochemistry 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 | -3.4 ± 0.96 | kJ/mol | Ccb | Hildenbrand, Sinke, et al., 1959 | |
ΔfH°gas | -3.6 ± 0.92 | kJ/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 | -41.0 ± 0.84 | kJ/mol | Ccb | Hildenbrand, Sinke, et al., 1959 | ALS |
ΔfH°liquid | -41.2 ± 0.84 | kJ/mol | Ccb | McCullough, Douslin, et al., 1959 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -2819.3 ± 0.84 | kJ/mol | Ccb | Hildenbrand, Sinke, et al., 1959 | ALS |
ΔcH°liquid | -2819.2 ± 0.75 | kJ/mol | Ccb | McCullough, Douslin, et al., 1959 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°liquid | 204.10 | J/mol*K | N/A | Hildenbrand, Sinke, et al., 1959 | DH |
S°liquid | 204.01 | J/mol*K | N/A | McCullough, Douslin, et al., 1959 | DH |
Constant pressure heat capacity of liquid
Cp,liquid (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
160.2 | 298. | Conti, Gianni, et al., 1976 | DH |
156.57 | 298.15 | Hildenbrand, Sinke, et al., 1959 | T = 14 to 312 K.; DH |
156.57 | 298.15 | McCullough, Douslin, et al., 1959 | T = 13 to 350 K.; DH |
Phase change 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:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
AC - William E. Acree, Jr., James S. Chickos
CAL - James S. Chickos, William E. Acree, Jr., Joel F. Liebman, Students of Chem 202 (Introduction to the Literature of Chemistry), University of Missouri -- St. Louis
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 360. ± 3. | K | AVG | N/A | Average of 7 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 211.95 | K | N/A | Boord, Greenlee, et al., 1950 | Uncertainty assigned by TRC = 0.5 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 215.31 | K | N/A | Hildenbrand, Sinke, et al., 1959, 2 | Crystal phase 1 phase; Uncertainty assigned by TRC = 0.07 K; TRC |
Ttriple | 215.240 | K | N/A | McCullough, Douslin, et al., 1959, 2 | Crystal phase 1 phase; Uncertainty assigned by TRC = 0.05 K; by extrapolation of 1/F to 0; TRC |
Ttriple | 215.31 | K | N/A | McCullough, Douslin, et al., 1959, 2 | Crystal phase 1 phase; Uncertainty assigned by TRC = 0.06 K; TRC |
Ttriple | 215.3 | K | N/A | Helm, Lanum, et al., 1958 | Uncertainty assigned by TRC = 0.03 K; measured in calorimeter at USBM, Bartlesville, OK; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 568.6 | K | N/A | Majer and Svoboda, 1985 | |
Tc | 568.6 | K | N/A | Cheng, McCoubrey, et al., 1962 | Uncertainty assigned by TRC = 0.4 K; TRC |
Tc | 570. | K | N/A | Kobe, Ravicz, et al., 1956 | Uncertainty assigned by TRC = 2.5 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Pc | 57.00 | bar | N/A | Kobe, Ravicz, et al., 1956 | Uncertainty assigned by TRC = 1.034 bar; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Vc | 0.249 | l/mol | N/A | Kobe, Ravicz, et al., 1956 | Uncertainty assigned by TRC = 0.005 l/mol; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 37.52 | kJ/mol | N/A | Majer and Svoboda, 1985 | |
ΔvapH° | 37.61 ± 0.10 | kJ/mol | V | Hildenbrand, Sinke, et al., 1959 | ALS |
ΔvapH° | 37.6 | kJ/mol | N/A | Hildenbrand, Sinke, et al., 1959 | DRB |
ΔvapH° | 37.57 ± 0.063 | kJ/mol | V | McCullough, Douslin, et al., 1959 | ALS |
ΔvapH° | 37.6 | kJ/mol | N/A | McCullough, Douslin, et al., 1959 | DRB |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
33.01 | 359.7 | N/A | Majer and Svoboda, 1985 | |
38.4 | 288. | A | Stephenson and Malanowski, 1987 | Based on data from 273. to 313. K.; AC |
35.8 | 331. | EB,IP | Stephenson and Malanowski, 1987 | Based on data from 316. to 394. K. See also McCullough, Douslin, et al., 1959 and Osborn and Douslin, 1968.; AC |
37.3 | 309. | N/A | Hildenbrand, Sinke, et al., 1959, 2 | Based on data from 294. to 360. K. See also Boublik, Fried, et al., 1984.; AC |
35.8 ± 0.1 | 322. | C | McCullough, Douslin, et al., 1959 | AC |
34.5 ± 0.1 | 340. | C | McCullough, Douslin, et al., 1959 | AC |
33.0 ± 0.1 | 360. | C | McCullough, Douslin, et al., 1959 | AC |
Enthalpy of vaporization
ΔvapH =
A exp(-βTr) (1 − Tr)β
ΔvapH =
Enthalpy of vaporization (at saturation pressure)
(kJ/mol)
Tr = reduced temperature (T / Tc)
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Temperature (K) | A (kJ/mol) | β | Tc (K) | Reference | Comment |
---|---|---|---|---|---|
322. to 360. | 57.78 | 0.3426 | 568.6 | Majer and Svoboda, 1985 |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (bar)
T = temperature (K)
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Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
316.31 to 394.1 | 4.04953 | 1180.043 | -67.895 | McCullough, Douslin, et al., 1959 | Coefficents calculated by NIST from author's data. |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
8.58 | 215.3 | Domalski and Hearing, 1996 | AC |
Entropy of fusion
ΔfusS (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
2.61 | 207.1 | Domalski and Hearing, 1996 | CAL |
39.84 | 215.3 |
Enthalpy of phase transition
ΔHtrs (kJ/mol) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
0.531 | 207.14 | crystaline, II | crystaline, I | Hildenbrand, Sinke, et al., 1959 | DH |
8.590 | 215.31 | crystaline, I | liquid | Hildenbrand, Sinke, et al., 1959 | DH |
0.5401 | 207.14 | crystaline, II | crystaline, I | McCullough, Douslin, et al., 1959 | DH |
8.577 | 215.31 | crystaline, I | liquid | McCullough, Douslin, et al., 1959 | DH |
Entropy of phase transition
ΔStrs (J/mol*K) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
2.56 | 207.14 | crystaline, II | crystaline, I | Hildenbrand, Sinke, et al., 1959 | DH |
39.90 | 215.31 | crystaline, I | liquid | Hildenbrand, Sinke, et al., 1959 | DH |
2.61 | 207.14 | crystaline, II | crystaline, I | McCullough, Douslin, et al., 1959 | DH |
39.84 | 215.31 | crystaline, I | liquid | McCullough, Douslin, et al., 1959 | 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° | 64.0 | kJ/mol | PHPMS | Hiraoka, Takimoto, et al., 1987 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 102. | J/mol*K | PHPMS | Hiraoka, Takimoto, et al., 1987 | gas phase; M |
By formula: C4H10N+ + C4H9N = (C4H10N+ • C4H9N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 93.3 | kJ/mol | PHPMS | Hiraoka, Takimoto, et al., 1987 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 99.6 | J/mol*K | PHPMS | Hiraoka, Takimoto, et al., 1987 | gas phase; M |
By formula: 3H2 + C12H21N3 = 3C4H9N
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -105. ± 0.4 | kJ/mol | Chyd | Wiberg, Nakaji, et al., 1993 | liquid phase; solvent: Acetic acid; ALS |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry 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]
Boord, Greenlee, et al., 1950
Boord, C.E.; Greenlee, K.W.; Derfer, J.M.,
The Synthesis, Purification and Prop. of Hydrocarbons of Low Mol. Wt., Am. Pet. Inst. Res. Proj. 45, Twelfth Annu. Rep., Ohio State Univ., 1950. [all data]
Hildenbrand, Sinke, et al., 1959, 2
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, 3, 650, https://doi.org/10.1063/1.1730441
. [all data]
McCullough, Douslin, et al., 1959, 2
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, 5884-90. [all data]
Helm, Lanum, et al., 1958
Helm, R.V.; Lanum, W.J.; Cook, G.L.; Ball, J.S.,
Purification and Properties of Pyrrole, Pyrrolidine, Pyridine and 2-Methylpyridine,
J. Phys. Chem., 1958, 62, 858. [all data]
Majer and Svoboda, 1985
Majer, V.; Svoboda, V.,
Enthalpies of Vaporization of Organic Compounds: A Critical Review and Data Compilation, Blackwell Scientific Publications, Oxford, 1985, 300. [all data]
Cheng, McCoubrey, et al., 1962
Cheng, D.C.H.; McCoubrey, J.C.; Phillips, D.G.,
Critical Temperatures of Some Organic Cyclic Compounds,
Trans. Faraday Soc., 1962, 58, 224. [all data]
Kobe, Ravicz, et al., 1956
Kobe, K.A.; Ravicz, A.E.; Vohra, S.P.,
Critical Properties and Vapor Pressures of Some Ethers and Heterocyclic Compounds,
J. Chem. Eng. Data, 1956, 1, 50. [all data]
Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw,
Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2
. [all data]
Osborn and Douslin, 1968
Osborn, Ann G.; Douslin, Donald R.,
Vapor pressure relations of 13 nitrogen compounds related to petroleum,
J. Chem. Eng. Data, 1968, 13, 4, 534-537, https://doi.org/10.1021/je60039a024
. [all data]
Boublik, Fried, et al., 1984
Boublik, T.; Fried, V.; Hala, E.,
The Vapour Pressures of Pure Substances: Selected Values of the Temperature Dependence of the Vapour Pressures of Some Pure Substances in the Normal and Low Pressure Region, 2nd ed., Elsevier, New York, 1984, 972. [all data]
Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D.,
Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III,
J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985
. [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]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, References
- Symbols used in this document:
Cp,liquid Constant pressure heat capacity of liquid Pc Critical pressure S°liquid Entropy of liquid at standard conditions Tboil Boiling point Tc Critical temperature Tfus Fusion (melting) point Ttriple Triple point temperature Vc Critical volume ΔHtrs Enthalpy of phase transition ΔStrs Entropy of phase transition 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 ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion ΔrH° Enthalpy of reaction at standard conditions ΔrS° Entropy of reaction at standard conditions ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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