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Piperidine

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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-11.27 ± 0.15kcal/molCcbGood, 1972Author was aware that data differs from previously reported values
Deltafgas-11.27 ± 0.15kcal/molCcbBedford, Beezer, et al., 1963Reanalyzed by Cox and Pilcher, 1970, Original value = -11.67 ± 0.61 kcal/mol

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
Deltafliquid-20.66 ± 0.14kcal/molCcbGood, 1972Author was aware that data differs from previously reported values; ALS
Deltafliquid-21.06 ± 0.54kcal/molCcbBedford, Beezer, et al., 1963ALS
Quantity Value Units Method Reference Comment
Deltacliquid-825.33 ± 0.12kcal/molCcbGood, 1972Author was aware that data differs from previously reported values; ALS
Deltacliquid-824.94 ± 0.56kcal/molCcbBedford, Beezer, et al., 1963ALS
Quantity Value Units Method Reference Comment
liquid50.1845cal/mol*KN/AMesserly, Todd, et al., 1988DH
liquid50.177cal/mol*KN/AMesserly, Todd, et al., 1987DH
liquid50.177cal/mol*KN/ASteele, Chirico, et al., 1986DH

Constant pressure heat capacity of liquid

Cp,liquid (cal/mol*K) Temperature (K) Reference Comment
42.9869298.150Messerly, Todd, et al., 1988T = 10 to 400 K.; DH
42.985298.15Messerly, Todd, et al., 1987T = 10 to 370 K.; DH
42.988298.15Steele, Chirico, et al., 1986T = 10 to 370 K.; DH
43.40298.Conti, Gianni, et al., 1976DH
43.681297.39Moelwyn-Hughes and Thorpe, 1964T = 297 to 327 K.; DH
44.50290.Kurnakov and Voskresenskaya, 1936DH
40.80290.Radulescu and Jula, 1934DH

Phase change data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry 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:
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., 1988, 2Uncertainty assigned by TRC = 0.03 K; TRC
Ttriple262.120KN/AMesserly, Todd, et al., 1988, 2Uncertainty 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
Pc45.9500atmN/AGuye and Mallet, 1902Uncertainty assigned by TRC = 2.0000 atm; rapid decomposition at critical temp.; TRC
Pc45.8500atmN/AGuye and Mallet, 1902Uncertainty assigned by TRC = 2.0000 atm; rapid decomposition at critical temp.; TRC
Quantity Value Units Method Reference Comment
Deltavap9.39kcal/molN/AGood, 1972DRB
Deltavap9.39 ± 0.05kcal/molVBedford, Beezer, et al., 1963ALS
Deltavap9.80kcal/molN/ABedford, Beezer, et al., 1963DRB

Reduced pressure boiling point

Tboil (K) Pressure (atm) Reference Comment
290.90.026Weast and Grasselli, 1989BS

Enthalpy of vaporization

DeltavapH (kcal/mol) Temperature (K) Method Reference Comment
8.75338.N/AHossenlopp and Archer, 1988AC
8.44357.N/AHossenlopp and Archer, 1988AC
8.99330.A,EB,IPStephenson and Malanowski, 1987Based on data from 315. - 417. K. See also Osborn and Douslin, 1968.; AC

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
315.51 - 416.763.976181239.577-67.622Osborn and Douslin, 1968

Enthalpy of fusion

DeltafusH (kcal/mol) Temperature (K) Reference Comment
3.550118262.124Messerly, Todd, et al., 1988DH
3.54873262.124Messerly, Todd, et al., 1987DH
3.549262.1Domalski and Hearing, 1996AC

Entropy of fusion

DeltafusS (cal/mol*K) Temperature (K) Reference Comment
13.54262.124Messerly, Todd, et al., 1988DH
13.54262.124Messerly, 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:


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 by: 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

Pyridine + 3Hydrogen = Piperidine

By formula: C5H5N + 3H2 = C5H11N

Quantity Value Units Method Reference Comment
Deltar-46.31 ± 0.18kcal/molEqkHales and Herington, 1957gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -48.32 ± 0.18 kcal/mol; At 400-550 K
Deltar-46.12 ± 0.50kcal/molEqkBurrows and King, 1935liquid phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -45.00 kcal/mol; At 423-443 K

3Hydrogen + Dodecahydro-1H,6H,11H-tripyrido[1,2-a:1',2'-c:1",2"-e][1,3,5]triazine = 3Piperidine

By formula: 3H2 + C15H27N3 = 3C5H11N

Quantity Value Units Method Reference Comment
Deltar-30.2 ± 0.5kcal/molChydWiberg, Nakaji, et al., 1993liquid phase; solvent: Acetic acid

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 compiled by: Coblentz Society, Inc.

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director


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

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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 Japan AIST/NIMC Database- Spectrum MS-NW- 539
NIST MS number 228351

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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.

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. 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]

Steele, Chirico, et al., 1986
Steele, W.V.; Chirico, R.D.; Collier, W.B.; Hossenlopp, I.A.; Nguyen, A.; Strube, M.M., Thermochemical and thermophysical properties of organic nitrogen compounds found in fossil materials, NIPER Report, 1986, 188, 112p. [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]

Moelwyn-Hughes and Thorpe, 1964
Moelwyn-Hughes, E.A.; Thorpe, P.L., The physical and thermodynamic properties of some associated solutions. II. Heat capacities and compressibilities, Proc. Roy. Soc. (London), 1964, 278A, 574-587. [all data]

Kurnakov and Voskresenskaya, 1936
Kurnakov, N.S.; Voskresenskaya, N.K., Calorimetry of liquid binary systems, Izv. Akad. Nauk SSSR, Otdel. Mat. i Estestv. Nauk. Ser. Khim, 1936, 1936, 439-461. [all data]

Radulescu and Jula, 1934
Radulescu, D.; Jula, O., Beiträge zur Bestimmung der Abstufung der Polarität des Aminstickstoffes in den organischen Verbindungen, Z. Phys. Chem., 1934, B26, 390-393. [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. 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]

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]

Hales and Herington, 1957
Hales, J.L.; Herington, E.F.G., Equilibrium between pyridine and piperidine, Trans. Faraday Soc., 1957, 53, 616-622. [all data]

Burrows and King, 1935
Burrows, G.H.; King, L.A., Jr., The free energy change that accompanies hydrogenation of pyridine to piperidine, J. Am. Chem. Soc., 1935, 57, 1789-1791. [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