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

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 7 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
Pc56.25atmN/AKobe, Ravicz, et al., 1956Uncertainty assigned by TRC = 1.020 atm; 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
Δvap8.967kcal/molN/AMajer and Svoboda, 1985 
Δvap8.990 ± 0.025kcal/molVHildenbrand, Sinke, et al., 1959ALS
Δvap8.99kcal/molN/AHildenbrand, Sinke, et al., 1959DRB
Δvap8.980 ± 0.015kcal/molVMcCullough, Douslin, et al., 1959ALS
Δvap8.99kcal/molN/AMcCullough, Douslin, et al., 1959DRB

Enthalpy of vaporization

ΔvapH (kcal/mol) Temperature (K) Method Reference Comment
7.890359.7N/AMajer and Svoboda, 1985 
9.18288.AStephenson and Malanowski, 1987Based on data from 273. to 313. K.; AC
8.56331.EB,IPStephenson and Malanowski, 1987Based on data from 316. to 394. K. See also McCullough, Douslin, et al., 1959 and Osborn and Douslin, 1968.; AC
8.91309.N/AHildenbrand, Sinke, et al., 1959, 2Based on data from 294. to 360. K. See also Boublik, Fried, et al., 1984.; AC
8.56 ± 0.02322.CMcCullough, Douslin, et al., 1959AC
8.25 ± 0.02340.CMcCullough, Douslin, et al., 1959AC
7.89 ± 0.02360.CMcCullough, Douslin, et al., 1959AC

Enthalpy of vaporization

ΔvapH = A exp(-βTr) (1 − Tr)β
    ΔvapH = Enthalpy of vaporization (at saturation pressure) (kcal/mol)
    Tr = reduced temperature (T / Tc)

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Temperature (K) A (kcal/mol) β Tc (K) Reference Comment
322. to 360.13.810.3426568.6Majer and Svoboda, 1985 

Antoine Equation Parameters

log10(P) = A − (B / (T + C))
    P = vapor pressure (atm)
    T = temperature (K)

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Temperature (K) A B C Reference Comment
316.31 to 394.14.043821180.043-67.895McCullough, Douslin, et al., 1959Coefficents calculated by NIST from author's data.

Enthalpy of fusion

ΔfusH (kcal/mol) Temperature (K) Reference Comment
2.05215.3Domalski and Hearing, 1996AC

Entropy of fusion

ΔfusS (cal/mol*K) Temperature (K) Reference Comment
0.624207.1Domalski and Hearing, 1996CAL
9.522215.3

Enthalpy of phase transition

ΔHtrs (kcal/mol) Temperature (K) Initial Phase Final Phase Reference Comment
0.127207.14crystaline, IIcrystaline, IHildenbrand, Sinke, et al., 1959DH
2.053215.31crystaline, IliquidHildenbrand, Sinke, et al., 1959DH
0.1291207.14crystaline, IIcrystaline, IMcCullough, Douslin, et al., 1959DH
2.050215.31crystaline, IliquidMcCullough, Douslin, et al., 1959DH

Entropy of phase transition

ΔStrs (cal/mol*K) Temperature (K) Initial Phase Final Phase Reference Comment
0.612207.14crystaline, IIcrystaline, IHildenbrand, Sinke, et al., 1959DH
9.536215.31crystaline, IliquidHildenbrand, Sinke, et al., 1959DH
0.624207.14crystaline, IIcrystaline, IMcCullough, Douslin, et al., 1959DH
9.522215.31crystaline, 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:


Henry's Law 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: Rolf Sander

Henry's Law constant (water solution)

kH(T) = H exp(d(ln(kH))/d(1/T) ((1/T) - 1/(298.15 K)))
H = Henry's law constant for solubility in water at 298.15 K (mol/(kg*bar))
d(ln(kH))/d(1/T) = Temperature dependence constant (K)

H (mol/(kg*bar)) d(ln(kH))/d(1/T) (K) Method Reference
420.7600.MN/A

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, Phase change data, Henry's Law 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]

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]

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

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