Piperidine
- Formula: C5H11N
- Molecular weight: 85.1475
- IUPAC Standard InChIKey: NQRYJNQNLNOLGT-UHFFFAOYSA-N
- CAS Registry Number: 110-89-4
- Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
The 3d structure may be viewed using Java or Javascript. - Other names: Azacyclohexane; Cyclopentimine; Cypentil; Hexahydropyridine; Hexazane; Pentamethylenimine; Pyridine, hexahydro-; Pentamethyleneimine; Piperidin; UN 2401; Perhydropyridine; Pentamethyleneamine
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Gas phase ion energetics data
Go To: Top, 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
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 ± 0.11 | eV | N/A | N/A | L |
Quantity | Value | Units | Method | Reference | Comment |
Proton affinity (review) | 954.0 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 921. | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
8.20 ± 0.05 | PE | Rozeboom and Houk, 1982 | LBLHLM |
8.05 ± 0.05 | PE | Pesterev, Gabdrakipov, et al., 1979 | LLK |
7.8 | PE | Aue and Bowers, 1979 | LLK |
7.9 ± 0.1 | PE | Aue, Webb, et al., 1976 | LLK |
8.7 | EI | Kiser and Gallegos, 1962 | RDSH |
9.15 | CTS | Collin, 1960 | RDSH |
8.65 ± 0.10 | PE | Gan and Peel, 1979 | Vertical value; LLK |
8.67 | PE | Daamen and Oskam, 1978 | Vertical value; LLK |
8.64 ± 0.05 | PE | Morishima, Yoshikawa, et al., 1975 | Vertical value; LLK |
8.66 ± 0.03 | PE | Colonna, Distefano, et al., 1975 | Vertical value; LLK |
8.660 | PE | Aue, Webb, et al., 1975 | Vertical value; LLK |
8.64 ± 0.02 | PE | Yoshikawa, Hashimoto, et al., 1974 | Vertical value; LLK |
Gas Chromatography
Go To: Top, Gas phase ion energetics 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: NIST Mass Spectrometry Data Center, William E. Wallace, director
Kovats' RI, non-polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Packed | C78, Branched paraffin | 130. | 762.0 | Dallos, Sisak, et al., 2000 | He; Column length: 3.3 m |
Capillary | OV-101 | 110. | 769. | Zhuravleva, 2000 | 50. m/0.3 mm/0.4 μm, He |
Capillary | OV-101 | 110. | 771. | Zhuravleva, Golovnya, et al., 1993 | 50. m/0.30 mm/0.40 μm, He |
Packed | C78, Branched paraffin | 130. | 762.0 | Reddy, Dutoit, et al., 1992 | Chromosorb G HP; Column length: 3.3 m |
Packed | Apolane | 130. | 766. | Dutoit, 1991 | Column length: 3.7 m |
Packed | OV-101 | 120. | 764. | Litvinenko, Isakova, et al., 1988 | He, Chromaton W AW; Column length: 2.4 m |
Packed | SE-30 | 150. | 775. | Tiess, 1984 | Ar, Gas Chrom Q (80-100 mesh); Column length: 3. m |
Packed | Apiezon L | 100. | 770. | Zhuravleva, Kapustin, et al., 1976 | N2 or He, Chromosorb G, AW; Column length: 2.7 m |
Packed | PMS-100 | 130. | 742. | Anderson, Jurel, et al., 1973 | He, Celite 545 (44-60 mesh); Column length: 3. m |
Packed | PMS-100 | 150. | 751. | Anderson, Jurel, et al., 1973 | He, Celite 545 (44-60 mesh); Column length: 3. m |
Packed | PMS-100 | 180. | 761. | Anderson, Jurel, et al., 1973 | He, Celite 545 (44-60 mesh); Column length: 3. m |
Kovats' RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Packed | SE-30 | 790. | Ramsey, Lee, et al., 1980 | He, Chromosorb G HP (80-100 mesh); Column length: 1.5 m; Program: not specified |
Kovats' RI, polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Packed | PEG-2000 | 150. | 1074. | Anderson, Jurel, et al., 1973 | He, Celite 545 (44-60 mesh); Column length: 3. m |
Packed | PEG-2000 | 152. | 1097. | Anderson, Jurel, et al., 1973 | He, Celite 545 (44-60 mesh); Column length: 3. m |
Packed | PEG-2000 | 179. | 1115. | Anderson, Jurel, et al., 1973 | He, Celite 545 (44-60 mesh); Column length: 3. m |
Packed | PEG-2000 | 180. | 1088. | Anderson, Jurel, et al., 1973 | He, Celite 545 (44-60 mesh); Column length: 3. m |
Packed | PEG-2000 | 200. | 1100. | Anderson, Jurel, et al., 1973 | He, Celite 545 (44-60 mesh); Column length: 3. m |
Packed | PEG-2000 | 200. | 1125. | Anderson, Jurel, et al., 1973 | He, Celite 545 (44-60 mesh); Column length: 3. m |
Van Den Dool and Kratz RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Packed | SE-30 | 775. | Peng, Ding, et al., 1988 | He, 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
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Methyl Silicone | 767. | Farkas, Héberger, et al., 2004 | Program: not specified |
Capillary | SE-30 | 750. | Vinogradov, 2004 | Program: not specified |
Capillary | SPB-1 | 755. | Flanagan, Streete, et al., 1997 | 60. m/0.53 mm/5. μm, He; Program: 40C(6min) => 5C/min => 80C => 10C/min => 200C |
Capillary | SPB-1 | 755. | Strete, Ruprah, et al., 1992 | 60. m/0.53 mm/5.0 μm, Helium; Program: 40 0C (6 min) 5 0C/min -> 80 0C 10 0C/min -> 200 0C |
Capillary | SPB-1 | 782. | Strete, Ruprah, et al., 1992 | 60. m/0.53 mm/5.0 μm, Helium; Program: not specified |
Capillary | OV-1, SE-30, Methyl silicone, SP-2100, OV-101, DB-1, etc. | 790. | Waggott and Davies, 1984 | Hydrogen; Column length: 50. m; Column diameter: 0.32 mm; Program: not specified |
Other | Methyl Silicone | 790. | Ardrey and Moffat, 1981 | Program: not specified |
Normal alkane RI, polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Carbowax 20M | 1042. | Vinogradov, 2004 | Program: not specified |
Capillary | DB-Wax | 1049. | Peng, Yang, et al., 1991 | Program: not specified |
References
Go To: Top, Gas phase ion energetics data, Gas Chromatography, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
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]
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 ion energetics data, Gas Chromatography, References
- Symbols used in this document:
IE (evaluated) Recommended ionization energy - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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