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Piperidine, 1-methyl-

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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 by: Eugene S. Domalski and Elizabeth D. Hearing

Constant pressure heat capacity of liquid

Cp,liquid (cal/mol*K) Temperature (K) Reference
44.19298.Conti, Gianni, et al., 1976

Phase change 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:
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
Tboil380.2KN/AWeast and Grasselli, 1989BS
Tboil378.85KN/ALanum and Morris, 1969Uncertainty assigned by TRC = 0.2 K; TRC
Tboil379.05KN/AMagnusson and Schierz, 1940Uncertainty assigned by TRC = 0.5 K; TRC
Tboil379.65KN/ARau and Narayanaswamy, 1934Uncertainty assigned by TRC = 0.5 K; TRC
Tboil390.15KN/ALoffler, 1910Uncertainty assigned by TRC = 3. K; TRC
Quantity Value Units Method Reference Comment
Deltavap8.8 ± 0.1kcal/molCRibeiro da Silva, Cabral, et al., 2006AC
Deltavap8.8 ± 0.1kcal/molCRibeiro da Silva, Cabral, et al., 2006AC
Deltavap8.77 ± 0.02kcal/molN/ABerthon, Angot, et al., 1979See also Ewing and Sanchez Ochoa, 1998.; AC

Enthalpy of vaporization

DeltavapH (kcal/mol) Temperature (K) Method Reference Comment
8.72313.N/ABelaribi, Ait-Kaci, et al., 1995Based on data from 298. - 343. K.; AC
8.91288.AStephenson and Malanowski, 1987Based on data from 273. - 380. K.; AC

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:


Henry's Law 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: Rolf Sander

Henry's Law constant (water solution)

kH(T) = H exp(d(ln(kH))/d(1/T) ((1/T) - 1/(298.15 K)))
H = Henry's law constant for solubility in water at 298.15 K (mol/kg*bar)
d(ln(kH))/d(1/T) = Temperature dependence constant (K)

H (mol/kg*bar) d(ln(kH))/d(1/T) (K) Method Reference
29.7900.MN/A

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

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)232.1kcal/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity224.7kcal/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
7.80 ± 0.05PERozeboom and Houk, 1982LBLHLM
7.74 ± 0.05PEPesterev, Gabdrakipov, et al., 1979LLK
8.35PESpanka and Rademacher, 1986Vertical value; LBLHLM
8.29PESarneel, Worrell, et al., 1980Vertical value; LLK
8.29 ± 0.02PEAue, Webb, et al., 1976Vertical value; LLK
8.29 ± 0.05PEMorishima, Yoshikawa, et al., 1975Vertical value; LLK
8.29 ± 0.02PEYoshikawa, Hashimoto, et al., 1974Vertical value; LLK

IR 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: Coblentz Society, Inc.

Condensed Phase Spectrum

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IR spectrum
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Notice: Except where noted, spectra from this collection were measured on dispersive instruments, often in carefully selected solvents, and hence may differ in detail from measurements on FTIR instruments or in other chemical environments. More information on the manner in which spectra in this collection were collected can be found here.

Notice: Concentration information is not available for this spectrum and, therefore, molar absorptivity values cannot be derived.

Additional Data

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Owner COBLENTZ SOCIETY
Collection (C) 2018 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin DOW CHEMICAL COMPANY
Source reference COBLENTZ NO. 1888
Date Not specified, most likely prior to 1970
Name(s) 1-methylpiperidine
State LIQUID
Instrument Not specified, most likely a prism, grating, or hybrid spectrometer.
Path length SMEAR
Resolution 4
Sampling procedure TRANSMISSION
Data processing DIGITIZED BY NIST FROM HARD COPY
Boiling point 98 C AT 732 mmHg

This IR spectrum is from the Coblentz Society's evaluated infrared reference spectra collection.


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

View image of digitized spectrum (can be printed in landscape orientation).

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Download spectrum in JCAMP-DX format.

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-3134
NIST MS number 229230

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.


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
CapillaryOV-101110.766.Zhuravleva, 200050. m/0.3 mm/0.4 «mu»m, He
CapillaryOV-101110.769.Zhuravleva, Golovnya, et al., 199350. m/0.30 mm/0.40 «mu»m, He
PackedApiezon L100.779.Zhuravleva, Kapustin, et al., 1976N2 or He, Chromosorb G, AW; Column length: 2.7 m
PackedPMS-100130.750.Anderson, Jurel, et al., 1973He, Celite 545 (44-60 mesh); Column length: 3. m
PackedPMS-100150.760.Anderson, Jurel, et al., 1973He, Celite 545 (44-60 mesh); Column length: 3. m
PackedPMS-100180.763.Anderson, Jurel, et al., 1973He, Celite 545 (44-60 mesh); Column length: 3. m

Kovats' RI, polar column, isothermal

View large format table.

Column type Active phase Temperature (C) I Reference Comment
CapillaryPEG-40M110.928.Zhuravleva, Golovnya, et al., 199350. m/0.30 mm/0.40 «mu»m, He
CapillaryPEG-40M+KF110.934.Svetlova, Samusenko, et al., 1986 
PackedPEG-2000150.957.Anderson, Jurel, et al., 1973He, Celite 545 (44-60 mesh); Column length: 3. m
PackedPEG-2000152.967.Anderson, Jurel, et al., 1973He, Celite 545 (44-60 mesh); Column length: 3. m
PackedPEG-2000179.986.Anderson, Jurel, et al., 1973He, Celite 545 (44-60 mesh); Column length: 3. m
PackedPEG-2000180.981.Anderson, Jurel, et al., 1973He, Celite 545 (44-60 mesh); Column length: 3. m
PackedPEG-2000200.1003.Anderson, Jurel, et al., 1973He, Celite 545 (44-60 mesh); Column length: 3. m
PackedPEG-2000200.999.Anderson, Jurel, et al., 1973He, Celite 545 (44-60 mesh); Column length: 3. m

Normal alkane RI, non-polar column, temperature ramp

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Column type Active phase I Reference Comment
CapillaryOV-101769.Zenkevich, 200525. m/0.20 mm/0.10 «mu»m, N2/He, 6. K/min; Tstart: 50. C; Tend: 250. C
CapillaryDB-1749.Flath, Matsumoto, et al., 198960. m/0.32 mm/0.25 «mu»m, 4. K/min; Tstart: 50. C; Tend: 250. C
CapillaryDB-1750.Flath, Matsumoto, et al., 198960. m/0.32 mm/0.25 «mu»m, 4. K/min; Tstart: 50. C; Tend: 250. C

Normal alkane RI, non-polar column, custom temperature program

View large format table.

Column type Active phase I Reference Comment
CapillaryMethyl Silicone769.Farkas, Héberger, et al., 2004Program: not specified

Normal alkane RI, polar column, custom temperature program

View large format table.

Column type Active phase I Reference Comment
CapillaryHP-Innowax959.Viegas and Bassoli, 200760. m/0.32 mm/0.25 «mu»m, Helium; Program: 40 0C (5 min) 4 0C/min -> 60 0C (5 min) 8 0C/min -> 250 0C (3 min)
CapillaryDB-Wax1020.Peng, Yang, et al., 1991Program: not specified

References

Go To: Top, Condensed phase thermochemistry data, Phase change data, Henry's Law data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, NIST Free Links, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

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]

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/«pi» 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 «pi» 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]

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]

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]

Svetlova, Samusenko, et al., 1986
Svetlova, N.I.; Samusenko, A.L.; Golovnya, R.V., Advantage of the universal equation over the linear equation for the calculation of retention parameters of homologous series in capillary chromatography, J. Hi. Res. Chromatogr. Chromatogr. Comm., 1986, 9, 12, 737-740, https://doi.org/10.1002/jhrc.1240091205 . [all data]

Zenkevich, 2005
Zenkevich, I.G., Experimentally measured retention indices., 2005. [all data]

Flath, Matsumoto, et al., 1989
Flath, R.A.; Matsumoto, K.E.; Binder, R.G.; Cunningham, R.T.; Mon, T.R., Effect of pH on the volatiles of hydrolyzed protein insect baits, J. Agric. Food Chem., 1989, 37, 3, 814-819, https://doi.org/10.1021/jf00087a053 . [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]

Viegas and Bassoli, 2007
Viegas, M.C.; Bassoli, D.G., Utilizacao do indice de retencao linear para caracterizacao de compostos volateis em cafe soluvel utilizando GC-MS e coluna HP-Innowax, Quim. Nova, 2007, 30, 8, 2031-2034, https://doi.org/10.1590/S0100-40422007000800040 . [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, Condensed phase thermochemistry data, Phase change data, Henry's Law data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, NIST Free Links, References