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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
Deltafgas-47.15 ± 0.63kJ/molCcbGood, 1972Author was aware that data differs from previously reported values
Deltafgas-47.15 ± 0.63kJ/molCcbBedford, Beezer, et al., 1963Reanalyzed by Cox and Pilcher, 1970, Original value = -48.8 ± 2.6 kJ/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-86.44 ± 0.59kJ/molCcbGood, 1972Author was aware that data differs from previously reported values; ALS
Deltafliquid-88.1 ± 2.3kJ/molCcbBedford, Beezer, et al., 1963ALS
Quantity Value Units Method Reference Comment
Deltacliquid-3453.2 ± 0.50kJ/molCcbGood, 1972Author was aware that data differs from previously reported values; ALS
Deltacliquid-3451.5 ± 2.3kJ/molCcbBedford, Beezer, et al., 1963ALS
Quantity Value Units Method Reference Comment
liquid209.972J/mol*KN/AMesserly, Todd, et al., 1988DH
liquid209.94J/mol*KN/AMesserly, Todd, et al., 1987DH
liquid209.94J/mol*KN/ASteele, Chirico, et al., 1986DH

Constant pressure heat capacity of liquid

Cp,liquid (J/mol*K) Temperature (K) Reference Comment
179.857298.150Messerly, Todd, et al., 1988T = 10 to 400 K.; DH
179.85298.15Messerly, Todd, et al., 1987T = 10 to 370 K.; DH
179.86298.15Steele, Chirico, et al., 1986T = 10 to 370 K.; DH
181.6298.Conti, Gianni, et al., 1976DH
182.76297.39Moelwyn-Hughes and Thorpe, 1964T = 297 to 327 K.; DH
186.2290.Kurnakov and Voskresenskaya, 1936DH
170.7290.Radulescu and Jula, 1934DH

Reaction thermochemistry data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, 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-193.8 ± 0.75kJ/molEqkHales and Herington, 1957gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -202.2 ± 0.75 kJ/mol; At 400-550 K
Deltar-193.0 ± 2.1kJ/molEqkBurrows and King, 1935liquid phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -188.3 kJ/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-126. ± 2.kJ/molChydWiberg, Nakaji, et al., 1993liquid phase; solvent: Acetic acid

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry 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. 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]

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, Reaction thermochemistry data, References