Pyrrolidine

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Gas phase thermochemistry data

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, UV/Visible spectrum, Gas Chromatography, 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
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:


Reaction thermochemistry data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, UV/Visible spectrum, Gas Chromatography, 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+ • 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

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, UV/Visible spectrum, Gas Chromatography, References, Notes

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

IR Spectrum

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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: 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 .


UV/Visible spectrum

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Gas Chromatography, 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: Victor Talrose, Eugeny B. Stern, Antonina A. Goncharova, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina

Spectrum

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UVVis spectrum
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1.) Enter the desired X axis range (e.g., 100, 200)
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Additional Data

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Source Pickett, Corning, et al., 1953
Owner INEP CP RAS, NIST OSRD
Collection (C) 2007 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin INSTITUTE OF ENERGY PROBLEMS OF CHEMICAL PHYSICS, RAS
Source reference RAS UV No. 794
Instrument Fluorite prism vacuum spectrograph or Beckman spectrophotometer, Model DU
Melting point -57.8
Boiling point 86.5

Gas Chromatography

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, UV/Visible 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

Kovats' RI, non-polar column, isothermal

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Column type Active phase Temperature (C) I Reference Comment
CapillaryOV-101110.692.Zhuravleva, 200050. m/0.3 mm/0.4 μm, He
PackedC78, Branched paraffin130.674.9Reddy, Dutoit, et al., 1992Chromosorb G HP; Column length: 3.3 m
PackedApolane130.680.Dutoit, 1991Column length: 3.7 m
PackedApiezon L100.690.Zhuravleva, Kapustin, et al., 1976N2 or He, Chromosorb G, AW; Column length: 2.7 m
PackedPMS-100130.645.Anderson, Jurel, et al., 1973He, Celite 545 (44-60 mesh); Column length: 3. m
PackedSE-30110.688.Tibor and Anna, 1971N2, Chromosorb W-AW; Column length: 2. m
PackedSE-3090.678.Tibor and Anna, 1971N2, Chromosorb W-AW; Column length: 2. m

Kovats' RI, non-polar column, custom temperature program

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Column type Active phase I Reference Comment
PackedSE-30695.Ramsey, Lee, et al., 1980He, Chromosorb G HP (80-100 mesh); Column length: 1.5 m; Program: not specified

Kovats' RI, polar column, isothermal

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Column type Active phase Temperature (C) I Reference Comment
PackedPEG-2000150.1008.Anderson, Jurel, et al., 1973He, Celite 545 (44-60 mesh); Column length: 3. m
PackedPEG-2000152.1038.Anderson, Jurel, et al., 1973He, Celite 545 (44-60 mesh); Column length: 3. m
PackedPEG-2000179.1040.Anderson, Jurel, et al., 1973He, Celite 545 (44-60 mesh); Column length: 3. m
PackedPEG-2000180.999.Anderson, Jurel, et al., 1973He, Celite 545 (44-60 mesh); Column length: 3. m
PackedPEG-2000200.1047.Anderson, Jurel, et al., 1973He, Celite 545 (44-60 mesh); Column length: 3. m
PackedPEG-2000200.994.Anderson, Jurel, et al., 1973He, Celite 545 (44-60 mesh); Column length: 3. m
PackedPEG-20M110.995.Tibor and Anna, 1971N2, Chromosorb W-AW; Column length: 2. m

Van Den Dool and Kratz RI, non-polar column, temperature ramp

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Column type Active phase I Reference Comment
PackedSE-30675.Peng, Ding, et al., 1988He, Supelcoport and Chromosorb, 40. C @ 4. min, 10. K/min, 250. C @ 60. min; Column length: 3.05 m

Normal alkane RI, non-polar column, temperature ramp

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Column type Active phase I Reference Comment
CapillaryOptima-5 MS660.Goeminne, Vandendriessche, et al., 201230. m/0.25 mm/0.25 μm, Helium, 35. C @ 3. min, 10. K/min, 250. C @ 5. min

Normal alkane RI, non-polar column, custom temperature program

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Column type Active phase I Reference Comment
CapillaryMethyl Silicone686.Farkas, Héberger, et al., 2004Program: not specified
CapillarySPB-1671.Flanagan, Streete, et al., 199760. m/0.53 mm/5. μm, He; Program: 40C(6min) => 5C/min => 80C => 10C/min => 200C
CapillarySPB-1671.Strete, Ruprah, et al., 199260. m/0.53 mm/5.0 μm, Helium; Program: 40 0C (6 min) 5 0C/min -> 80 0C 10 0C/min -> 200 0C
CapillarySPB-1695.Strete, Ruprah, et al., 199260. m/0.53 mm/5.0 μm, Helium; Program: not specified
CapillaryOV-1, SE-30, Methyl silicone, SP-2100, OV-101, DB-1, etc.695.Waggott and Davies, 1984Hydrogen; Column length: 50. m; Column diameter: 0.32 mm; Program: not specified
CapillaryOV-1695.Ramsey and Flanagan, 1982Program: not specified
OtherMethyl Silicone695.Ardrey and Moffat, 1981Program: not specified

Normal alkane RI, polar column, temperature ramp

View large format table.

Column type Active phase I Reference Comment
CapillaryDB-Wax1020.Rochat, Egger, et al., 200930. m/0.25 mm/0.25 μm, Helium, 60. C @ 3. min, 8. K/min, 200. C @ 9.5 min
CapillaryDB-Wax1031.Rochat, Egger, et al., 200930. m/0.25 mm/0.25 μm, Helium, 60. C @ 3. min, 8. K/min, 200. C @ 9.5 min
CapillaryDB-Wax1032.Rochat, Egger, et al., 200930. m/0.25 mm/0.25 μm, Helium, 60. C @ 3. min, 8. K/min, 200. C @ 9.5 min
CapillaryDB-Wax1034.Rochat, Egger, et al., 200930. m/0.25 mm/0.25 μm, Helium, 60. C @ 3. min, 8. K/min, 200. C @ 9.5 min

Normal alkane RI, polar column, custom temperature program

View large format table.

Column type Active phase I Reference Comment
CapillaryDB-Wax1006.Rochat, Egger, et al., 200930. m/0.25 mm/0.25 μm, Helium; Program: not specified
CapillaryDB-Wax1003.Peng, Yang, et al., 1991Program: not specified
CapillaryCarbowax 20M1022.Ramsey and Flanagan, 1982Program: not specified

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, UV/Visible spectrum, Gas Chromatography, 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]

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
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Notes

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