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Pyrrolidine

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Gas phase thermochemistry data

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), 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
Deltafgas-3.4 ± 0.96kJ/molCcbHildenbrand, Sinke, et al., 1959 
Deltafgas-3.6 ± 0.92kJ/molCcbMcCullough, Douslin, et al., 1959 

Condensed phase thermochemistry data

Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), 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:
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
Deltafliquid-41.0 ± 0.84kJ/molCcbHildenbrand, Sinke, et al., 1959ALS
Deltafliquid-41.2 ± 0.84kJ/molCcbMcCullough, Douslin, et al., 1959ALS
Quantity Value Units Method Reference Comment
Deltacliquid-2819.3 ± 0.84kJ/molCcbHildenbrand, Sinke, et al., 1959ALS
Deltacliquid-2819.2 ± 0.75kJ/molCcbMcCullough, Douslin, et al., 1959ALS
Quantity Value Units Method Reference Comment
liquid204.10J/mol*KN/AHildenbrand, Sinke, et al., 1959DH
liquid204.01J/mol*KN/AMcCullough, Douslin, et al., 1959DH

Constant pressure heat capacity of liquid

Cp,liquid (J/mol*K) Temperature (K) Reference Comment
160.2298.Conti, Gianni, et al., 1976DH
156.57298.15Hildenbrand, Sinke, et al., 1959T = 14 to 312 K.; DH
156.57298.15McCullough, Douslin, et al., 1959T = 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
Tboil360. ± 3.KAVGN/AAverage of 8 values; Individual data points
Quantity Value Units Method Reference Comment
Tfus211.95KN/ABoord, Greenlee, et al., 1950Uncertainty assigned by TRC = 0.5 K; TRC
Quantity Value Units Method Reference Comment
Ttriple215.31KN/AHildenbrand, Sinke, et al., 1959, 2Crystal phase 1 phase; Uncertainty assigned by TRC = 0.07 K; TRC
Ttriple215.240KN/AMcCullough, Douslin, et al., 1959, 2Crystal phase 1 phase; Uncertainty assigned by TRC = 0.05 K; by extrapolation of 1/F to 0; TRC
Ttriple215.31KN/AMcCullough, Douslin, et al., 1959, 2Crystal phase 1 phase; Uncertainty assigned by TRC = 0.06 K; TRC
Ttriple215.3KN/AHelm, Lanum, et al., 1958Uncertainty assigned by TRC = 0.03 K; measured in calorimeter at USBM, Bartlesville, OK; TRC
Quantity Value Units Method Reference Comment
Tc568.6KN/AMajer and Svoboda, 1985 
Tc568.6KN/ACheng, McCoubrey, et al., 1962Uncertainty assigned by TRC = 0.4 K; TRC
Tc570.KN/AKobe, Ravicz, et al., 1956Uncertainty assigned by TRC = 2.5 K; TRC
Quantity Value Units Method Reference Comment
Pc57.00barN/AKobe, Ravicz, et al., 1956Uncertainty assigned by TRC = 1.034 bar; TRC
Quantity Value Units Method Reference Comment
Vc0.249l/molN/AKobe, Ravicz, et al., 1956Uncertainty assigned by TRC = 0.005 l/mol; TRC
Quantity Value Units Method Reference Comment
Deltavap37.52kJ/molN/AMajer and Svoboda, 1985 
Deltavap37.61 ± 0.10kJ/molVHildenbrand, Sinke, et al., 1959ALS
Deltavap37.6kJ/molN/AHildenbrand, Sinke, et al., 1959DRB
Deltavap37.57 ± 0.063kJ/molVMcCullough, Douslin, et al., 1959ALS
Deltavap37.6kJ/molN/AMcCullough, Douslin, et al., 1959DRB

Enthalpy of vaporization

DeltavapH (kJ/mol) Temperature (K) Method Reference Comment
33.01359.7N/AMajer and Svoboda, 1985 
38.4288.AStephenson and Malanowski, 1987Based on data from 273. - 313. K.; AC
35.8331.EB,IPStephenson and Malanowski, 1987Based on data from 316. - 394. K. See also McCullough, Douslin, et al., 1959 and Osborn and Douslin, 1968.; AC
37.3309.N/AHildenbrand, Sinke, et al., 1959, 2Based on data from 294. - 360. K. See also Boublik, Fried, et al., 1984.; AC
35.8 ± 0.1322.CMcCullough, Douslin, et al., 1959AC
34.5 ± 0.1340.CMcCullough, Douslin, et al., 1959AC
33.0 ± 0.1360.CMcCullough, Douslin, et al., 1959AC

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) beta Tc (K) Reference Comment
322. - 360.57.780.3426568.6Majer 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 - 394.14.049531180.043-67.895McCullough, Douslin, et al., 1959Coefficents calculated by NIST from author's data.

Enthalpy of fusion

DeltafusH (kJ/mol) Temperature (K) Reference Comment
8.58215.3Domalski and Hearing, 1996AC

Entropy of fusion

DeltafusS (J/mol*K) Temperature (K) Reference Comment
2.61207.1Domalski and Hearing, 1996CAL
39.84215.3

Enthalpy of phase transition

DeltaHtrs (kJ/mol) Temperature (K) Initial Phase Final Phase Reference Comment
0.531207.14crystaline, IIcrystaline, IHildenbrand, Sinke, et al., 1959DH
8.590215.31crystaline, IliquidHildenbrand, Sinke, et al., 1959DH
0.5401207.14crystaline, IIcrystaline, IMcCullough, Douslin, et al., 1959DH
8.577215.31crystaline, IliquidMcCullough, Douslin, et al., 1959DH

Entropy of phase transition

DeltaStrs (J/mol*K) Temperature (K) Initial Phase Final Phase Reference Comment
2.56207.14crystaline, IIcrystaline, IHildenbrand, Sinke, et al., 1959DH
39.90215.31crystaline, IliquidHildenbrand, Sinke, et al., 1959DH
2.61207.14crystaline, IIcrystaline, IMcCullough, Douslin, et al., 1959DH
39.84215.31crystaline, IliquidMcCullough, Douslin, et al., 1959DH

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:


Reaction thermochemistry data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, IR Spectrum, Mass spectrum (electron ionization), 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:
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+ bullet Pyrrolidine) + Pyrrolidine = (C4H10N+ bullet 2Pyrrolidine)

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

Quantity Value Units Method Reference Comment
Deltar64.0kJ/molPHPMSHiraoka, Takimoto, et al., 1987gas phase; M
Quantity Value Units Method Reference Comment
Deltar102.J/mol*KPHPMSHiraoka, Takimoto, et al., 1987gas phase; M

C4H10N+ + Pyrrolidine = (C4H10N+ bullet Pyrrolidine)

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

Quantity Value Units Method Reference Comment
Deltar93.3kJ/molPHPMSHiraoka, Takimoto, et al., 1987gas phase; M
Quantity Value Units Method Reference Comment
Deltar99.6J/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
Deltar-105. ± 0.4kJ/molChydWiberg, Nakaji, et al., 1993liquid phase; solvent: Acetic acid; ALS

IR Spectrum

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Mass spectrum (electron ionization), 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: NIST Mass Spectrometry Data Center, William E. Wallace, director

Gas Phase Spectrum

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IR spectrum
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Notice: Concentration information is not available for this spectrum and, therefore, molar absorptivity values cannot be derived.

Additional Data

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Owner NIST Standard Reference Data Program
Collection (C) 2018 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin NIST Mass Spectrometry Data Center
State gas
Instrument HP-GC/MS/IRD

This IR spectrum is from the NIST/EPA Gas-Phase Infrared Database .


Mass spectrum (electron ionization)

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, 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: NIST Mass Spectrometry Data Center, William E. Wallace, director

Spectrum

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Mass spectrum
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Additional Data

View image of digitized spectrum (can be printed in landscape orientation).

View spectrum image in SVG format.

Download spectrum in JCAMP-DX format.

Owner NIST Mass Spectrometry Data Center
Collection (C) 2014 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin NIST Mass Spectrometry Data Center, 1990.
NIST MS number 118205

All mass spectra in this site (plus many more) are available from the NIST/EPA/NIH Mass Spectral Library. Please see the following for information about the library and its accompanying search program.


References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), 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, IR Spectrum, Mass spectrum (electron ionization), References