Piperidine, 1-methyl-
- Formula: C6H13N
- Molecular weight: 99.1741
- IUPAC Standard InChIKey: PAMIQIKDUOTOBW-UHFFFAOYSA-N
- CAS Registry Number: 626-67-5
- 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: N-Methylpiperidine; 1-Methylpiperidine; UN 2399
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Phase change data
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 as indicated in comments:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 380.2 | K | N/A | Weast and Grasselli, 1989 | BS |
Tboil | 378.85 | K | N/A | Lanum and Morris, 1969 | Uncertainty assigned by TRC = 0.2 K; TRC |
Tboil | 379.05 | K | N/A | Magnusson and Schierz, 1940 | Uncertainty assigned by TRC = 0.5 K; TRC |
Tboil | 379.65 | K | N/A | Rau and Narayanaswamy, 1934 | Uncertainty assigned by TRC = 0.5 K; TRC |
Tboil | 390.15 | K | N/A | Loffler, 1910 | Uncertainty assigned by TRC = 3. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 36.8 ± 0.6 | kJ/mol | C | Ribeiro da Silva, Cabral, et al., 2006 | AC |
ΔvapH° | 36.8 ± 0.6 | kJ/mol | C | Ribeiro da Silva, Cabral, et al., 2006 | AC |
ΔvapH° | 36.7 ± 0.1 | kJ/mol | N/A | Berthon, Angot, et al., 1979 | See also Ewing and Sanchez Ochoa, 1998.; AC |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
36.5 | 313. | N/A | Belaribi, Ait-Kaci, et al., 1995 | Based on data from 298. to 343. K.; AC |
37.3 | 288. | A | Stephenson and Malanowski, 1987 | Based on data from 273. to 380. K.; AC |
Gas phase ion energetics data
Go To: Top, Phase change data, 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
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
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Proton affinity (review) | 971.1 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 940.1 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
7.80 ± 0.05 | PE | Rozeboom and Houk, 1982 | LBLHLM |
7.74 ± 0.05 | PE | Pesterev, Gabdrakipov, et al., 1979 | LLK |
8.35 | PE | Spanka and Rademacher, 1986 | Vertical value; LBLHLM |
8.29 | PE | Sarneel, Worrell, et al., 1980 | Vertical value; LLK |
8.29 ± 0.02 | PE | Aue, Webb, et al., 1976 | Vertical value; LLK |
8.29 ± 0.05 | PE | Morishima, Yoshikawa, et al., 1975 | Vertical value; LLK |
8.29 ± 0.02 | PE | Yoshikawa, Hashimoto, et al., 1974 | Vertical value; LLK |
References
Go To: Top, Phase change 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.
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]
Lanum and Morris, 1969
Lanum, W.J.; Morris, J.C.,
Physical Properties of Some Sulfur and Nitrogen Compounds,
J. Chem. Eng. Data, 1969, 14, 93-8. [all data]
Magnusson and Schierz, 1940
Magnusson, H.W.; Schierz, E.R.,
A Study of SOme Physical Constants of N-n-Alkylpiperidines,
Univ. Wyo. Publ., 1940, 7, 1. [all data]
Rau and Narayanaswamy, 1934
Rau, M.A.G.; Narayanaswamy, B.N.,
The determination of dipole moments using the method of diluted solutions: I and II,
Z. Phys. Chem., Abt. B, 1934, 26, 23. [all data]
Loffler, 1910
Loffler, K.,
A New Synthesis of N-Alkyl Pyrrolidines,
Chem. Ber., 1910, 43, 2035. [all data]
Ribeiro da Silva, Cabral, et al., 2006
Ribeiro da Silva, Manuel A.V.; Cabral, Joana I.T.A.; Gomes, Paula; Gomes, José R.B.,
Combined Experimental and Computational Study of the Thermochemistry of Methylpiperidines,
J. Org. Chem., 2006, 71, 10, 3677-3685, https://doi.org/10.1021/jo052468w
. [all data]
Berthon, Angot, et al., 1979
Berthon, Guy; Angot, Bernard; Beden, Bernard; Enea, Octavian,
Quantitative comparison of substituent effects on solvation and proton-ionization standard enthalpies of methylpiperidines,
The Journal of Chemical Thermodynamics, 1979, 11, 6, 539-546, https://doi.org/10.1016/0021-9614(79)90092-2
. [all data]
Ewing and Sanchez Ochoa, 1998
Ewing, M.B.; Sanchez Ochoa, J.C.,
An ebulliometer for measurements of vapour pressure at low temperatures: the vapour pressures and the critical state of perfluoromethylcyclopentane,
The Journal of Chemical Thermodynamics, 1998, 30, 2, 189-198, https://doi.org/10.1006/jcht.1997.0290
. [all data]
Belaribi, Ait-Kaci, et al., 1995
Belaribi, F.B.; Ait-Kaci, A.; Jose, J.,
Equilibres liquide-vapeur isothermes de melanges binaires de la piperidine et de la N-methyl piperidine avec certains ethers,
Journal of Thermal Analysis, 1995, 44, 5, 1177-1194, https://doi.org/10.1007/BF02547548
. [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]
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]
Spanka and Rademacher, 1986
Spanka, G.; Rademacher, P.,
Transannular interactions in difunctional medium rings. 1. n/π Interactions in cyclic amino ketones and aminoalkenes studied by photoelectron spectroscopy,
J. Org. Chem., 1986, 51, 592. [all data]
Sarneel, Worrell, et al., 1980
Sarneel, R.; Worrell, C.W.; Pasman, P.; Verhoeven, J.W.; Mes, G.F.,
The photoelectron spectra of 4-methylene thiacyclohexane derivatives through-bond interaction,
Tetrahedron, 1980, 36, 3241. [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]
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]
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, Phase change data, Gas phase ion energetics data, References
- Symbols used in this document:
Tboil Boiling point ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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