2-Methylpiperidine

• Formula: C₆H₁₃N
• Molecular weight: 99.1741
• IUPAC Standard InChI: InChI=1S/C6H13N/c1-6-4-2-3-5-7-6/h6-7H,2-5H2,1H3 Copy

  
• IUPAC Standard InChIKey: NNWUEBIEOFQMSS-UHFFFAOYSA-N Copy
• CAS Registry Number: 109-05-7
• 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.
• Stereoisomers:
  • Piperidin, 2e-methyl
• Other names: 2-Pipecoline; α-Methylpiperidine; α-Pipecoline; Pipicoline; Piperidine, 2-methyl-; α-Pipecolin; Pipecoline, α
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Gas phase thermochemistry data
  • Phase change data
  • Gas phase ion energetics data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • Gas Chromatography
  • References
  • Notes
• Other data available:
  • Condensed phase thermochemistry data
• Options:
  • Switch to SI units

Data at NIST subscription sites:

• NIST / TRC Web Thermo Tables, professional edition (thermophysical and thermochemical data)

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.

Gas phase thermochemistry data

Go To: Top, Phase change data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), 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 compiled by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Phase change data

Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), 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 compiled as indicated in comments:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
BS - Robert L. Brown and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
AC - William E. Acree, Jr., James S. Chickos

Reduced pressure boiling point

Enthalpy of vaporization

Antoine Equation Parameters

log₁₀(P) = A − (B / (T + C))
    P = vapor pressure (atm)
    T = temperature (K)

View plot Requires a JavaScript / HTML 5 canvas capable browser.

Enthalpy of fusion

Gas phase ion energetics data

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

Ionization energy determinations

IR Spectrum

Go To: Top, Gas phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), Gas Chromatography, References, Notes

Data compiled by: Coblentz Society, Inc.

• Not specified, most likely a prism, grating, or hybrid spectrometer.; DIGITIZED BY NIST FROM HARD COPY; 4 cm^-1 resolution

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

• gas; HP-GC/MS/IRD

Mass spectrum (electron ionization)

Go To: Top, Gas phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, 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 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.

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

Gas Chromatography

Go To: Top, Gas 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: NIST Mass Spectrometry Data Center, William E. Wallace, director

Kovats' RI, non-polar column, isothermal

View large format table.

Kovats' RI, polar column, isothermal

View large format table.

Normal alkane RI, non-polar column, temperature ramp

View large format table.

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

View large format table.

Normal alkane RI, polar column, custom temperature program

View large format table.

References

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

Bruhl, 1895
Bruhl, J.W., Spectrochemistry of Nitrogen-Containing Compounds. I., Z. Phys. Chem., Stoechiom. Verwandtschaftsl., 1895, 16, 193. [all data]

Steele, Chirico, et al., 1986
Steele, W.V.; Chirico, R.D.; Collier, W.B.; Hossenlopp, I.A.; Nguyen, A.; Strube, M.M., Thermochemical and thermophysical properties of organic nitrogen compounds found in fossil materials, NIPER Report, 1986, 188, 112p. [all data]

Messerly, Todd, et al., 1988
Messerly, J.F.; Todd, s.S.; Finke, H.L.; Good, W.D.; Gammon, B.E., Condensed-phase heat-capacity studies and derived thermodynamic properties for six cyclic nitrogen compounds, J. Chem. Thermodyn., 1988, 20, 209. [all data]

Anonymous, 1961
Anonymous, R., Preliminary thermodyn. prop. of FREON-14, E. I. Du Pont, Freon Tech. Bull. T-14, 1961. [all data]

Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc., Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [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]

Osborn and Douslin, 1968
Osborn, Ann G.; Douslin, Donald R., Vapor pressure relations of 13 nitrogen compounds related to petroleum, J. Chem. Eng. Data, 1968, 13, 4, 534-537, https://doi.org/10.1021/je60039a024 . [all data]

Messerly, Todd, et al., 1988, 2
Messerly, J.F.; Todd, S.S.; Finke, H.L.; Good, W.D.; Gammon, B.E., Condensed-phase heat-capacity studies and derived thermodynamic properties for six cyclic nitrogen compounds, J. Chem. Thermodynam., 1988, 20, 209-224. [all data]

Messerly, Todd, et al., 1987
Messerly, J.F.; Todd, S.S.; Finke, H.L.; Gammon, B.E., Thermodynamic properties of organic nitrogen compounds that occur in shale oil and heavy petroleum-topical report, NIPER Report, 1987, 83, 37p. [all data]

Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D., Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III, J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985 . [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]

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]

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

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, Phase change data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, References

• Symbols used in this document:
  

  IE (evaluated)	Recommended ionization energy
  Tboil	Boiling point
  Tfus	Fusion (melting) point
  Ttriple	Triple point temperature
  ΔfH°gas	Enthalpy of formation of gas at standard conditions
  ΔfusH	Enthalpy of fusion
  ΔvapH	Enthalpy of vaporization
  ΔvapH°	Enthalpy of vaporization at standard conditions

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
• The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment. However, NIST makes no warranties to that effect, and NIST shall not be liable for any damage that may result from errors or omissions in the Database.
• Customer support for NIST Standard Reference Data products.