Pyridine, 2,5-dimethyl-

• Formula: C₇H₉N
• Molecular weight: 107.1531
• IUPAC Standard InChI: InChI=1S/C7H9N/c1-6-3-4-7(2)8-5-6/h3-5H,1-2H3 Copy

  
• IUPAC Standard InChIKey: XWKFPIODWVPXLX-UHFFFAOYSA-N Copy
• CAS Registry Number: 589-93-5
• Chemical structure:
  This structure is also available as a 2d Mol file
• Other names: 2,5-Lutidine; 2,5-Dimethylpyridine; 5-methyl-2-methylpyridine
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • Henry's Law data
  • Gas phase ion energetics data
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
  • Gas Chromatography
  • References
  • Notes
• Options:
  • Switch to SI units

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Gas 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: Donald R. Burgess, Jr.

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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing

Constant pressure heat capacity of liquid

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
DH - Eugene S. Domalski and Elizabeth D. Hearing
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos

Enthalpy of vaporization

Antoine Equation Parameters

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

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Enthalpy of fusion

Temperature of phase transition

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)

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

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:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi

View reactions leading to C₇H₉N⁺ (ion structure unspecified)

Ionization energy determinations

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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Additional Data

UV/Visible 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: Victor Talrose, Alexander N. Yermakov, Alexy A. Usov, Antonina A. Goncharova, Axlexander N. Leskin, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina

Spectrum

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Additional Data

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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Kovats' RI, polar column, isothermal

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Van Den Dool and Kratz RI, non-polar column, temperature ramp

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Van Den Dool and Kratz RI, polar column, temperature ramp

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Normal alkane RI, non-polar column, temperature ramp

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

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Normal alkane RI, polar column, temperature ramp

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References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Henry's Law data, Gas phase ion energetics data, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, Notes

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

Cox and Gundry, 1958
Cox, J.D.; Gundry, H.A., Heats of combustion. Part II. The six lutidines, J. Chem. Soc., 1958, 1019-1022. [all data]

Cox, Challoner, et al., 1954
Cox, J.D.; Challoner, A.R.; Meetham, A.R., The heats of combustion of pyridine and certain of its derivatives, J. Chem. Soc., 1954, 265-271. [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]

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]

Jankun-Pinska, 1964
Jankun-Pinska, J., Liquid-liquid equilibrium in series of ternary systems formed by pyridine bases, benzene and water. II. ternary systems: 2,4-lutidine-benzene-water, 2,5-lutidine-benzene-water and 2,6-lutidine-b, Bull. Acad. Pol. Sci., Ser. Sci. Chim., 1964, 12, 843. [all data]

Prostakov, Gaivoronskaya, et al., 1963
Prostakov, N.S.; Gaivoronskaya, L.A.; Mikheeva, N.N.; Filippov, N.P., Substituted Pyridines: 2,5-Dimethyl-4-alkylpyridines, Zh. Obshch. Khim., 1963, 33, 2928. [all data]

Farberov, Kut'in, et al., 1961
Farberov, M.I.; Kut'in, A.M.; Ustavshchikov, V.F., The conditions of 2-methyl-5-vinylprydine synthesis, Zh. Prikl. Khim. (Leningrad), 1961, 34, 632. [all data]

Kyte, Jeffery, et al., 1960
Kyte, C.T.; Jeffery, G.H.; Vogel, A.I., Physical Properties and Chem. Constitution XXVII. Pyridine Derivatives, J. Chem. Soc., 1960, 1960, 4454. [all data]

Coulson, Cox, et al., 1959
Coulson, E.A.; Cox, J.D.; Herington, E.F.G.; Martin, J.F., The Preparation and Physical Properties of the Pure Lutidines, J. Chem. Soc., 1959, 1959, 1934. [all data]

Chirico, Hossenlopp, et al., 1994
Chirico, R.D.; Hossenlopp, I.A.; Gammon, B.E.; Knipmeyer, S.E.; Steele, W.V., Heat capacities of the six dimethylpyridines between the temperatures 10 K and 445 K and methyl-group rotational barriers in the solid state a,b, J. Chem. Thermodyn., 1994, 26, 11, 1187, https://doi.org/10.1006/jcht.1994.1138 . [all data]

Ambrose, Cox, et al., 1960
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Cox, 1960
Cox, J.D., The second virial coefficients, latent heats of vaporization and heats of formation of the lutidines, Trans. Faraday Soc., 1960, 56, 959. [all data]

Steele, Chirico, et al., 1995
Steele, W.V.; Chirico, R.D.; Nguyen, A.; Knipmeyer, S.E., Vapor pressures, high-temperature heat capacities, critical properties, derived thermodynamic functions, and barriers to methyl-group rotation, for the six dimethylpyridines, The Journal of Chemical Thermodynamics, 1995, 27, 3, 311-334, https://doi.org/10.1006/jcht.1995.0030 . [all data]

Stephenson and Malanowski, 1987
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Herington and Martin, 1953
Herington, E.F.G.; Martin, J.F., Vapour pressures of pyridine and its homologues, Trans. Faraday Soc., 1953, 49, 154, https://doi.org/10.1039/tf9534900154 . [all data]

Kkykj and Repas, 1973
Kkykj, J.; Repas, M., Petrochemia, 1973, 13, 179. [all data]

Herington and Martin, 1953, 2
Herington, E.F.G.; Martin, J.F., Vapour Pressures of Pyridine and its Homologues, Trans. Faraday Soc., 1953, 49, 154-162, https://doi.org/10.1039/tf9534900154 . [all data]

Chirico, Hossenlopp, et al., 1994, 2
Chirico, R.D.; Hossenlopp, I.A.; Gammon, B.E.; Knipmeyer, S.E.; Steele, W.V., Heat capacities of the six dimethylpyridines between the temperatures 10 K and 445 K and methyl-group rotational barriers in the solid state a,b, The Journal of Chemical Thermodynamics, 1994, 26, 11, 1187-1218, https://doi.org/10.1006/jcht.1994.1138 . [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]

Heilbronner, Hornung, et al., 1972
Heilbronner, E.; Hornung, V.; Pinkerton, F.H.; Thames, S.F., 31. Photoelectron spectra of azabenzenes and azanaphthalenes: III. The orbital sequence in methyl- and trimethylsilyl- substituted pyridines, Helv. Chim. Acta, 1972, 55, 289. [all data]

Andon and Herington, 1954
Andon, R.J.L.; Herington, E.F.G., Trans. Faraday Soc., 1954, 50, 918. [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]

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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]

Samusenko and Golovnya, 1988
Samusenko, A.L.; Golovnya, R.V., Prediction of the retention indices of methyl pyridines and pyrazines in capillary gas chromatography based on the non-linear additivity of the sorption energy, Chromatographia, 1988, 25, 6, 531-535, https://doi.org/10.1007/BF02324828 . [all data]

Morishita, Morimoto, et al., 1986
Morishita, F.; Morimoto, S.; Kojima, T., Prediction of molecular structures of aza-arenes by retention indices and fluorescence spectra, J. Hi. Res. Chromatogr. Chromatogr. Comm., 1986, 9, 11, 688-692, https://doi.org/10.1002/jhrc.1240091120 . [all data]

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Samusenko, A.L.; Svetlova, N.I.; Golovnya, R.V., Reproducible and durable glass capillary columns with hydrogenated apiezon-l and OV-101 for the analysis of polar substances, Zh. Anal. Khim., 1986, 61, 1, 127-133. [all data]

Shatts, Avots, et al., 1977
Shatts, V.D.; Avots, A.A.; Belikov, V.A., Retention indices of alkylpyridines, Zh. Anal. Khim., 1977, 32, 4, 631-638. [all data]

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Riedo, F.; Fritz, D.; Tarján, G.; Kováts, E.Sz., A tailor-made C₈₇ hydrocarbon as a possible non-polar standard stationary phase for gas chromatography, J. Chromatogr., 1976, 126, 63-83, https://doi.org/10.1016/S0021-9673(01)84063-2 . [all data]

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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]

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Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Henry's Law data, Gas phase ion energetics data, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, References

• Symbols used in this document:
  

  Cp,liquid	Constant pressure heat capacity of liquid
  S°liquid	Entropy of liquid at standard conditions
  Tboil	Boiling point
  Tc	Critical temperature
  Tfus	Fusion (melting) point
  Ttriple	Triple point temperature
  Ttrs	Temperature of phase transition
  d(ln(kH))/d(1/T)	Temperature dependence parameter for Henry's Law constant
  k°H	Henry's Law constant at 298.15K
  ΔcH°liquid	Enthalpy of combustion of liquid at standard conditions
  ΔfH°gas	Enthalpy of formation of gas at standard conditions
  ΔfH°liquid	Enthalpy of formation of liquid at standard conditions
  ΔfusH	Enthalpy of fusion
  ΔvapH	Enthalpy of vaporization
  ΔvapH°	Enthalpy of vaporization at standard conditions

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