Home Symbol which looks like a small house Up Solid circle with an upward pointer in it

NOTICE: Due to scheduled maintenance at our Gaithersburg campus, this site will not be available from 5:00 pm EDT (21:00 UTC) on Friday October 25 until 5:00 pm (21:00 UTC) on Sunday October 27. We apologize for any inconvenience this outage may cause.

Piperidine, 1-methyl-

Data at NIST subscription sites:

NIST subscription sites provide data under the NIST Standard Reference Data Program, but require an annual fee to access. The purpose of the fee is to recover costs associated with the development of data collections included in such sites. Your institution may already be a subscriber. Follow the links above to find out more about the data in these sites and their terms of usage.


Condensed phase thermochemistry data

Go To: Top, Phase change data, Henry's Law data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), 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: Eugene S. Domalski and Elizabeth D. Hearing

Constant pressure heat capacity of liquid

Cp,liquid (J/mol*K) Temperature (K) Reference
184.9298.Conti, Gianni, et al., 1976

Phase change data

Go To: Top, Condensed phase thermochemistry data, Henry's Law data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), 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
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
Deltavap36.8 ± 0.6kJ/molCRibeiro da Silva, Cabral, et al., 2006AC
Deltavap36.8 ± 0.6kJ/molCRibeiro da Silva, Cabral, et al., 2006AC
Deltavap36.7 ± 0.1kJ/molN/ABerthon, Angot, et al., 1979See also Ewing and Sanchez Ochoa, 1998.; AC

Enthalpy of vaporization

DeltavapH (kJ/mol) Temperature (K) Method Reference Comment
36.5313.N/ABelaribi, Ait-Kaci, et al., 1995Based on data from 298. - 343. K.; AC
37.3288.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

Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), 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: 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

Go To: Top, Condensed phase thermochemistry data, Phase change data, Henry's Law data, IR Spectrum, Mass spectrum (electron ionization), 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)971.1kJ/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity940.1kJ/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

Go To: Top, Condensed phase thermochemistry data, Phase change data, Henry's Law data, Gas phase ion energetics data, Mass spectrum (electron ionization), 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: Coblentz Society, Inc.

Condensed Phase Spectrum

Notice: This spectrum may be better viewed with a Javascript and HTML 5 enabled browser.

IR spectrum
For Zoom
1.) Enter the desired X axis range (e.g., 100, 200)
2.) Check here for automatic Y scaling
3.) Press here to zoom

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

View scan of original (hardcopy) spectrum.

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

View spectrum image in SVG format.

Download spectrum in JCAMP-DX format.

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)

Go To: Top, Condensed phase thermochemistry data, Phase change data, Henry's Law data, Gas phase ion energetics data, IR Spectrum, 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

Spectrum

Notice: This spectrum may be better viewed with a Javascript and HTML 5 enabled browser.

Mass spectrum
For Zoom
1.) Enter the desired X axis range (e.g., 100, 200)
2.) Check here for automatic Y scaling
3.) Press here to zoom

Additional Data

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

View spectrum image in SVG format.

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.


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), 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]


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), References