Piperidine

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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-47.15 ± 0.63kJ/molCcbGood, 1972Author was aware that data differs from previously reported values
Δfgas-47.15 ± 0.63kJ/molCcbBedford, Beezer, et al., 1963Reanalyzed by Cox and Pilcher, 1970, Original value = -48.8 ± 2.6 kJ/mol

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
DH - Eugene S. Domalski and Elizabeth D. Hearing
DRB - Donald R. Burgess, Jr.
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos

Quantity Value Units Method Reference Comment
Tboil379.2 ± 0.5KAVGN/AAverage of 16 values; Individual data points
Quantity Value Units Method Reference Comment
Tfus262. ± 5.KAVGN/AAverage of 7 values; Individual data points
Quantity Value Units Method Reference Comment
Ttriple262.100KN/AMesserly, Todd, et al., 1988Uncertainty assigned by TRC = 0.03 K; TRC
Ttriple262.120KN/AMesserly, Todd, et al., 1988Uncertainty assigned by TRC = 0.02 K; TRC
Ttriple262.12KN/AAnonymous, 1960Uncertainty assigned by TRC = 0.05 K; measured by Project 52c at Bartlesville OK; TRC
Quantity Value Units Method Reference Comment
Tc594.1KN/AAmbrose, 1963Uncertainty assigned by TRC = 0.02 K; TRC
Tc594.KN/ACheng, McCoubrey, et al., 1962Uncertainty assigned by TRC = 0.3 K; Visual (5-cm 2-mm bore tubes) in nitrate-nitrite bath, TE or TH cal. vs NPL thermometer J.C.McCoubrey, A.R.Ubbelohde Trans. Faraday Soc. 1960,56,114; TRC
Quantity Value Units Method Reference Comment
Pc46.5588barN/AGuye and Mallet, 1902Uncertainty assigned by TRC = 2.0265 bar; rapid decomposition at critical temp.; TRC
Pc46.4575barN/AGuye and Mallet, 1902Uncertainty assigned by TRC = 2.0265 bar; rapid decomposition at critical temp.; TRC
Quantity Value Units Method Reference Comment
Δvap39.3kJ/molN/AGood, 1972DRB
Δvap39.3 ± 0.2kJ/molVBedford, Beezer, et al., 1963ALS
Δvap41.0kJ/molN/ABedford, Beezer, et al., 1963DRB

Reduced pressure boiling point

Tboil (K) Pressure (bar) Reference Comment
290.90.027Weast and Grasselli, 1989BS

Enthalpy of vaporization

ΔvapH (kJ/mol) Temperature (K) Method Reference Comment
36.6338.N/AHossenlopp and Archer, 1988AC
35.3357.N/AHossenlopp and Archer, 1988AC
37.6330.A,EB,IPStephenson and Malanowski, 1987Based on data from 315. to 417. K. See also Osborn and Douslin, 1968.; AC

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
315.51 to 416.763.981891239.577-67.622Osborn and Douslin, 1968

Enthalpy of fusion

ΔfusH (kJ/mol) Temperature (K) Reference Comment
14.85369262.124Messerly, Todd, et al., 1988, 2DH
14.8479262.124Messerly, Todd, et al., 1987DH
14.85262.1Domalski and Hearing, 1996AC

Entropy of fusion

ΔfusS (J/mol*K) Temperature (K) Reference Comment
56.67262.124Messerly, Todd, et al., 1988, 2DH
56.64262.124Messerly, Todd, et al., 1987DH

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
220.7900.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
L - Sharon G. Lias

Data compiled as indicated in comments:
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
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
IE (evaluated)8.03 ± 0.11eVN/AN/AL
Quantity Value Units Method Reference Comment
Proton affinity (review)954.0kJ/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity921.kJ/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
8.20 ± 0.05PERozeboom and Houk, 1982LBLHLM
8.05 ± 0.05PEPesterev, Gabdrakipov, et al., 1979LLK
7.8PEAue and Bowers, 1979LLK
7.9 ± 0.1PEAue, Webb, et al., 1976LLK
8.7EIKiser and Gallegos, 1962RDSH
9.15CTSCollin, 1960RDSH
8.65 ± 0.10PEGan and Peel, 1979Vertical value; LLK
8.67PEDaamen and Oskam, 1978Vertical value; LLK
8.64 ± 0.05PEMorishima, Yoshikawa, et al., 1975Vertical value; LLK
8.66 ± 0.03PEColonna, Distefano, et al., 1975Vertical value; LLK
8.660PEAue, Webb, et al., 1975Vertical value; LLK
8.64 ± 0.02PEYoshikawa, Hashimoto, et al., 1974Vertical value; LLK

References

Go To: Top, Gas 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.

Good, 1972
Good, W.D., Enthalpies of combustion of nine organic nitrogen compounds related to petroleum, J. Chem. Eng. Data, 1972, 17, 28-31. [all data]

Bedford, Beezer, et al., 1963
Bedford, A.F.; Beezer, A.E.; Mortimer, C.T., Heats of formation and bond energies. Part X. 1,2,5,6-tetrahydropyridine, piperidine, and piperazine, J. Chem. Soc., 1963, 2039-2043. [all data]

Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]

Messerly, Todd, et al., 1988
Messerly, J.F.; Todd, s.S.; Finke, H.L.; Good, W.D.; Gammon, B.E., Condensed-phase heat-capacity studies and derived thermodynamic properties for six cyclic nitrogen compounds, J. Chem. Thermodyn., 1988, 20, 209. [all data]

Anonymous, 1960
Anonymous, R., , Natl. Bur. Stand. (U. S.), Tech. News Bull. 44, 1960. [all data]

Ambrose, 1963
Ambrose, D., Critical Temperatures of Some Phenols and Other Organic Compounds, Trans. Faraday Soc., 1963, 59, 1988. [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]

Guye and Mallet, 1902
Guye, P.A.; Mallet, E., Measurement of Critical Constants, Arch. Sci. Phys. Nat., 1902, 13, 274-296. [all data]

Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [all data]

Hossenlopp and Archer, 1988
Hossenlopp, I.A.; Archer, D.G., Enthalpies of vaporization of piperidine and 1,2-dimethylbenzene; gas-phase isobaric heat capacities of piperidine, The Journal of Chemical Thermodynamics, 1988, 20, 9, 1061-1068, https://doi.org/10.1016/0021-9614(88)90112-7 . [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]

Messerly, Todd, et al., 1988, 2
Messerly, J.F.; Todd, S.S.; Finke, H.L.; Good, W.D.; Gammon, B.E., Condensed-phase heat-capacity studies and derived thermodynamic properties for six cyclic nitrogen compounds, J. Chem. Thermodynam., 1988, 20, 209-224. [all data]

Messerly, Todd, et al., 1987
Messerly, J.F.; Todd, S.S.; Finke, H.L.; Gammon, B.E., Thermodynamic properties of organic nitrogen compounds that occur in shale oil and heavy petroleum-topical report, NIPER Report, 1987, 83, 37p. [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]

Rozeboom and Houk, 1982
Rozeboom, M.D.; Houk, K.N., Stereospecific alkyl group effects on amine lone-pair ionization potentials: Photoelectron spectra of alkylpiperidines, J. Am. Chem. Soc., 1982, 104, 1189. [all data]

Pesterev, Gabdrakipov, et al., 1979
Pesterev, V.I.; Gabdrakipov, V.Z.; Artyukhin, V.I.; Agashkin, O.V., The ionisation and excitation of the conformers of piperidine and its alkyl derivatives, Russ. J. Phys. Chem., 1979, 53, 845. [all data]

Aue and Bowers, 1979
Aue, D.H.; Bowers, M.T., Chapter 9. Stabilities of positive ions from equilibrium gas phase basicity measurements in Ions Chemistry,, ed. M.T. Bowers, 1979. [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]

Kiser and Gallegos, 1962
Kiser, R.W.; Gallegos, E.J., A technique for the rapid determination of ionization and appearance potentials, J. Phys. Chem., 1962, 66, 947. [all data]

Collin, 1960
Collin, J.E., Relations between charge-transfer spectra and ionization potentials of some electron-donor organic molecules, Z. Elektrochem., 1960, 64, 936. [all data]

Gan and Peel, 1979
Gan, T.-H.; Peel, J.B., Photoelectron spectroscopic studies of piperidine and its N-halo derivatives, Aust. J. Chem., 1979, 32, 475. [all data]

Daamen and Oskam, 1978
Daamen, H.; Oskam, A., Bonding properties of some monosubstituted chromium and tungsten hexacarbonyls M(CO)5L (L=amine, substituted pyridine, azine), Inorg. Chim. Acta, 1978, 26, 81. [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]

Aue, Webb, et al., 1975
Aue, D.H.; Webb, H.M.; Bowers, M.T., Proton affinities, ionization potentials, and hydrogen affinities of nitrogen and oxygen bases. Hybridization effects, J. Am. Chem. Soc., 1975, 97, 4137. [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]


Notes

Go To: Top, Gas phase thermochemistry data, Phase change data, Henry's Law data, Gas phase ion energetics data, References