Pyridine, 2,4-dimethyl-

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

  
• IUPAC Standard InChIKey: JYYNAJVZFGKDEQ-UHFFFAOYSA-N Copy
• CAS Registry Number: 108-47-4
• Chemical structure:
  This structure is also available as a 2d Mol file
• Other names: 2,4-Lutidine; α,γ-Dimethylpyridine; 2,4-Dimethylpyridine; 2,4-Lutidene
• 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
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
  • Gas Chromatography
  • References
  • Notes
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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
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Enthalpy of vaporization

Enthalpy of vaporization

Δ_vapH = A exp(-βT_r) (1 − T_r)^β
    Δ_vapH = Enthalpy of vaporization (at saturation pressure) (kJ/mol)
    T_r = reduced temperature (T / T_c)

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Antoine Equation Parameters

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

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Enthalpy of fusion

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:
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

View reactions leading to C₇H₉N⁺ (ion structure unspecified)

Ionization energy determinations

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

• VAPOR (0.5 MICROLITER AT 150 C); NICOLET FTIR; DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 4 CM^-1 cm^-1 resolution

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

• gas

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, Eugeny B. Stern, Antonina A. Goncharova, 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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Van Den Dool and Kratz RI, polar column, custom temperature program

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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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Normal alkane RI, polar column, custom temperature program

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Lee's RI, non-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, IR Spectrum, 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]

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]

Assal, 1966
Assal, F.A., Vapour-liquid equilibria in phenol-pyridine base systems, Bull. Acad. Pol. Sci., Ser. Sci. Chim., 1966, 14, 603. [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]

Majer and Svoboda, 1985
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Ambrose, D.; Grant, D.G., The Critical Temperatures of Some Hydrocarbons and Pyridine Bases, Trans. Faraday Soc., 1957, 53, 771. [all data]

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Chickos, James S.; Hosseini, Sarah; Hesse, Donald G., Determination of vaporization enthalpies of simple organic molecules by correlations of changes in gas chromatographic net retention times, Thermochimica Acta, 1995, 249, 41-62, https://doi.org/10.1016/0040-6031(95)90670-3 . [all data]

Cox, 1960
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Sakoguchi, Ueoka, et al., 1995
Sakoguchi, Akihiro; Ueoka, Ryuichi; Kato, Yasuo; Arai, Yasuhiko, Vapor Pressures of Alkylpyridines and Alkylpyrazines., KAGAKU KOGAKU RONBUNSHU, 1995, 21, 1, 219-223, https://doi.org/10.1252/kakoronbunshu.21.219 . [all data]

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Lencka, 1990
Lencka, Malgorzata, Measurements of the vapour pressures of pyridine, 2-methylpyridine, 2,4-dimethylpyridine, 2,6-dimethylpyridine, and 2,4,6-trimethylpyridine from 0.1 kPa to atmospheric pressure using a modified Swietoslawski ebulliometer, The Journal of Chemical Thermodynamics, 1990, 22, 5, 473-480, https://doi.org/10.1016/0021-9614(90)90139-H . [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]

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

Wisniewska, Lencka, et al., 1986
Wisniewska, Barbara; Lencka, Malgorzata; Rogalski, Marek, Vapour pressures of 2,4-, 2,6-, and 3,5-dimethylpyridine at temperatures from 267 to 360 K, The Journal of Chemical Thermodynamics, 1986, 18, 8, 703-708, https://doi.org/10.1016/0021-9614(86)90102-3 . [all data]

Majer, Svoboda, et al., 1985
Majer, V.; Svoboda, V.; Lencka, M., Enthalpies of vaporization and cohesive energies of dimethylpyridines and trimethylpyridines, The Journal of Chemical Thermodynamics, 1985, 17, 4, 365-370, https://doi.org/10.1016/0021-9614(85)90133-8 . [all data]

Coulson, Cox, et al., 1959, 2
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, 1934-1940, https://doi.org/10.1039/jr9590001934 . [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]

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Watanabe, K.; Nakayama, T.; Mottl, J., Ionization potentials of some molecules, J. Quant. Spectry. Radiative Transfer, 1962, 2, 369. [all data]

Andon, Cox, et al., 1954
Andon, R.J.L.; Cox, J.D.; Herington, E.F.G., The ultra-violet absorption spectra and dissociation constants of certain pyridine bases in aqueous solution, Trans. Faraday Soc., 1954, 50, 918-927. [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]

Reddy, Dutoit, et al., 1992
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]

Zhang, Li, et al., 1992
Zhang, M.J.; Li, S.D.; Chen, B.J., Compositional studies of high-temperature coal tar by GC/FTIR analysis of light oil fractions, Chromatographia, 1992, 33, 3/4, 138-146, https://doi.org/10.1007/BF02275894 . [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]

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]

Riedo, Fritz, et al., 1976
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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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]

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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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Golovnya, R.V.; Samusenko, A.L.; Dmitriev, L.B., Predicting retention indices of methyl-substituted pyridines in gas capillary chromatogrpahy on the basis of the principle of the nonadditive change in the energy of sorption, Izv. Akad. Nauk SSSR Ser. Khim., 1987, 10, 2234-2239. [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, IR Spectrum, 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
  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

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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