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

Reaction 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

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
Δr-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
Δr-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
Δr-126. ± 2.kJ/molChydWiberg, Nakaji, et al., 1993liquid phase; solvent: Acetic acid

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

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

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


Mass spectrum (electron ionization)

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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

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

All mass spectra in this site (plus many more) are available from the NIST/EPA/NIH Mass Spectral Library. Please see the following for information about the library and its accompanying search program.


UV/Visible 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: 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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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. 819
Instrument Fluorite prism vacuum spectrograph or Beckman DU
Melting point -11.03
Boiling point 106.2

Gas Chromatography

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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

Kovats' RI, non-polar column, isothermal

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Column type Active phase Temperature (C) I Reference Comment
PackedC78, Branched paraffin130.762.0Dallos, Sisak, et al., 2000He; Column length: 3.3 m
CapillaryOV-101110.769.Zhuravleva, 200050. m/0.3 mm/0.4 μm, He
CapillaryOV-101110.771.Zhuravleva, Golovnya, et al., 199350. m/0.30 mm/0.40 μm, He
PackedC78, Branched paraffin130.762.0Reddy, Dutoit, et al., 1992Chromosorb G HP; Column length: 3.3 m
PackedApolane130.766.Dutoit, 1991Column length: 3.7 m
PackedOV-101120.764.Litvinenko, Isakova, et al., 1988He, Chromaton W AW; Column length: 2.4 m
PackedSE-30150.775.Tiess, 1984Ar, Gas Chrom Q (80-100 mesh); Column length: 3. m
PackedApiezon L100.770.Zhuravleva, Kapustin, et al., 1976N2 or He, Chromosorb G, AW; Column length: 2.7 m
PackedPMS-100130.742.Anderson, Jurel, et al., 1973He, Celite 545 (44-60 mesh); Column length: 3. m
PackedPMS-100150.751.Anderson, Jurel, et al., 1973He, Celite 545 (44-60 mesh); Column length: 3. m
PackedPMS-100180.761.Anderson, Jurel, et al., 1973He, Celite 545 (44-60 mesh); Column length: 3. m

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

View large format table.

Column type Active phase I Reference Comment
PackedSE-30790.Ramsey, Lee, et al., 1980He, Chromosorb G HP (80-100 mesh); Column length: 1.5 m; Program: not specified

Kovats' RI, polar column, isothermal

View large format table.

Column type Active phase Temperature (C) I Reference Comment
PackedPEG-2000150.1074.Anderson, Jurel, et al., 1973He, Celite 545 (44-60 mesh); Column length: 3. m
PackedPEG-2000152.1097.Anderson, Jurel, et al., 1973He, Celite 545 (44-60 mesh); Column length: 3. m
PackedPEG-2000179.1115.Anderson, Jurel, et al., 1973He, Celite 545 (44-60 mesh); Column length: 3. m
PackedPEG-2000180.1088.Anderson, Jurel, et al., 1973He, Celite 545 (44-60 mesh); Column length: 3. m
PackedPEG-2000200.1100.Anderson, Jurel, et al., 1973He, Celite 545 (44-60 mesh); Column length: 3. m
PackedPEG-2000200.1125.Anderson, Jurel, et al., 1973He, Celite 545 (44-60 mesh); Column length: 3. m

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

View large format table.

Column type Active phase I Reference Comment
PackedSE-30775.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, custom temperature program

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Column type Active phase I Reference Comment
CapillaryMethyl Silicone767.Farkas, Héberger, et al., 2004Program: not specified
CapillarySE-30750.Vinogradov, 2004Program: not specified
CapillarySPB-1755.Flanagan, Streete, et al., 199760. m/0.53 mm/5. μm, He; Program: 40C(6min) => 5C/min => 80C => 10C/min => 200C
CapillarySPB-1755.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-1782.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.790.Waggott and Davies, 1984Hydrogen; Column length: 50. m; Column diameter: 0.32 mm; Program: not specified
OtherMethyl Silicone790.Ardrey and Moffat, 1981Program: not specified

Normal alkane RI, polar column, custom temperature program

View large format table.

Column type Active phase I Reference Comment
CapillaryCarbowax 20M1042.Vinogradov, 2004Program: not specified
CapillaryDB-Wax1049.Peng, Yang, et al., 1991Program: not specified

References

Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), 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.

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]

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]

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]

Pickett, Corning, et al., 1953
Pickett, L.W.; Corning, M.E.; Wieder, G.M.; Semenow, D.A.; Buckley, J.M., The vacuum ultraviolet spectra of cyclic compounds. III. Amines, J. Am. Chem. Soc., 1953, 75, 1618-1622. [all data]

Dallos, Sisak, et al., 2000
Dallos, A.; Sisak, A.; Kulcsár, Z.; Kováts, E., Pair-wise interactions by gas chromatography VII. Interaction free enthalpies of solutes with secondary alcohol groups, J. Chromatogr. A, 2000, 904, 2, 211-242, https://doi.org/10.1016/S0021-9673(00)00908-0 . [all data]

Zhuravleva, 2000
Zhuravleva, I.L., Evaluation of the polarity and boiling points of nitrogen-containing heterocyclic compounds by gas chromatography, Russ. Chem. Bull. (Engl. Transl.), 2000, 49, 2, 325-328, https://doi.org/10.1007/BF02494682 . [all data]

Zhuravleva, Golovnya, et al., 1993
Zhuravleva, I.L.; Golovnya, R.V.; Kuzmenko, T.E., The regularities of the gas-chromatographic behavior of methyl-substituted N-alkylpiperidines, Russ. Chem. Bull. (Engl. Transl.), 1993, 42, 10, 1677-1679, https://doi.org/10.1007/BF00697038 . [all data]

Reddy, Dutoit, et al., 1992
Reddy, K.S.; Dutoit, J.-Cl.; Kovats, E. sz., Pair-wise interactions by gas chromatography. I. Interaction free enthalpies of solutes with non-associated primary alcohol groups, J. Chromatogr., 1992, 609, 1-2, 229-259, https://doi.org/10.1016/0021-9673(92)80167-S . [all data]

Dutoit, 1991
Dutoit, J., Gas chromatographic retention behaviour of some solutes on structurally similar polar and non-polar stationary phases, J. Chromatogr., 1991, 555, 1-2, 191-204, https://doi.org/10.1016/S0021-9673(01)87179-X . [all data]

Litvinenko, Isakova, et al., 1988
Litvinenko, G.S.; Isakova, L.A.; Rubanyk, N.N., Quantitative correlation between structure of stereoisomeric saturated cyclic compounds and gas-chromatographic retention indices. I. Methysubstituted, Izv. AN Kaz. SSR, Ser. Khim., 1988, 5, 54-66. [all data]

Tiess, 1984
Tiess, D., Gaschromatographische Retentionsindices von 125 leicht- bis mittelflüchtigen organischen Substanzen toxikologisch-analytischer Relevanz auf SE-30, Wiss. Z. Wilhelm-Pieck-Univ. Rostock Math. Naturwiss. Reihe, 1984, 33, 6-9. [all data]

Zhuravleva, Kapustin, et al., 1976
Zhuravleva, I.L.; Kapustin, Yu.P.; Golovnya, P.B., Retention indices of some isoaliphatic and heterocyclic nitrogenous bases, Zh. Anal. Khim., 1976, 31, 1378-1380. [all data]

Anderson, Jurel, et al., 1973
Anderson, A.; Jurel, S.; Shymanska, M.; Golender, L., Gas-liquid chromatography of some aliphatic and heterocyclic mono- and pollyfunctional amines. VII. Retention indices of amines in some polar and unpolar stationary phases, Latv. PSR Zinat. Akad. Vestis Kim. Ser., 1973, 1, 51-63. [all data]

Ramsey, Lee, et al., 1980
Ramsey, J.D.; Lee, T.D.; Osselton, M.D.; Moffat, A.C., Gas-liquid chromatographic retention indices of 296 non-drug substances on SE-30 or OV-1 likely to be encountered in toxicological analyses, J. Chromatogr., 1980, 184, 2, 185-206, https://doi.org/10.1016/S0021-9673(00)85641-1 . [all data]

Peng, Ding, et al., 1988
Peng, C.T.; Ding, S.F.; Hua, R.L.; Yang, Z.C., Prediction of Retention Indexes I. Structure-Retention Index Relationship on Apolar Columns, J. Chromatogr., 1988, 436, 137-172, https://doi.org/10.1016/S0021-9673(00)94575-8 . [all data]

Farkas, Héberger, et al., 2004
Farkas, O.; Héberger, K.; Zenkevich, I.G., Quantitative structure-retention relationships. XIV. Prediction of gas chromatographic retention indices for saturated O-, N-, and S-heterocyclic compounds, Chemom. Intell. Lab. Syst., 2004, 72, 2, 173-184, https://doi.org/10.1016/j.chemolab.2004.01.012 . [all data]

Vinogradov, 2004
Vinogradov, B.A., Production, composition, properties and application of essential oils, 2004, retrieved from http://viness.narod.ru. [all data]

Flanagan, Streete, et al., 1997
Flanagan, R.J.; Streete, P.J.; Ramsey, J.D., Volatile Substance Abuse, UNODC Technical Series, No 5, United Nations, Office on Drugs and Crime, Vienna International Centre, PO Box 500, A-1400 Vienna, Austria, 1997, 56, retrieved from http://www.odccp.org/pdf/technicalseries1997-01-011.pdf. [all data]

Strete, Ruprah, et al., 1992
Strete, P.J.; Ruprah, M.; Ramsey, J.D.; Flanagan, R.J., Detection and identification of volatile substances by headspace capillary gas chromatography to aid the diagnosis of acute poisoning, Analyst, 1992, 117, 7, 1111-1127, https://doi.org/10.1039/an9921701111 . [all data]

Waggott and Davies, 1984
Waggott, A.; Davies, I.W., Identification of organic pollutants using linear temperature programmed retention indices (LTPRIs) - Part II, 1984, retrieved from http://dwi.defra.gov.uk/research/completed-research/reports/dwi0383.pdf. [all data]

Ardrey and Moffat, 1981
Ardrey, R.E.; Moffat, A.C., Gas-liquid chromatographic retention indices of 1318 substances of toxicological interest on SE-30 or OV-1 stationary phase, J. Chromatogr., 1981, 220, 3, 195-252, https://doi.org/10.1016/S0021-9673(00)81925-1 . [all data]

Peng, Yang, et al., 1991
Peng, C.T.; Yang, Z.C.; Ding, S.F., Prediction of rentention idexes. II. Structure-retention index relationship on polar columns, J. Chromatogr., 1991, 586, 1, 85-112, https://doi.org/10.1016/0021-9673(91)80028-F . [all data]


Notes

Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, References