Pyridine, 3,5-dimethyl-

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

  
• IUPAC Standard InChIKey: HWWYDZCSSYKIAD-UHFFFAOYSA-N Copy
• CAS Registry Number: 591-22-0
• Chemical structure:
  This structure is also available as a 2d Mol file
• Other names: 3,5-Dimethylpyridine; 3,5-Lutidine
• 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
  • Mass spectrum (electron ionization)
  • Gas Chromatography
  • References
  • Notes
• Other data available:
  • Condensed phase thermochemistry data
  • Henry's Law data
  • Gas phase ion energetics data
  • IR Spectrum
  • UV/Visible spectrum
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Gas phase thermochemistry data

Go To: Top, Phase change data, 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: Donald R. Burgess, Jr.

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

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

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, 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, Phase change data, 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.

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]

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

Majer and Svoboda, 1985
Majer, V.; Svoboda, V., Enthalpies of Vaporization of Organic Compounds: A Critical Review and Data Compilation, Blackwell Scientific Publications, Oxford, 1985, 300. [all data]

Jankun-Pinska, 1965
Jankun-Pinska, J., Liquid-liquid equilibrium in series of ternary systems formed by pyridine bases benzene and water. III. 3,5-lutidine-benzene-water and 2,4,6-collidine-benzene-water, Bull. Acad. Pol. Sci., Ser. Sci. Chim., 1965, 13, 121. [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]

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
Ambrose, D.; Cox, J.D.; Townsend, R., The critical temperatures of forty organic compounds, Trans. Faraday Soc., 1960, 56, 1452. [all data]

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]

Ben-makhlouf-Hakem, Ait-Kaci, et al., 2005
Ben-makhlouf-Hakem, Hamama; Ait-Kaci, Ahmed; Jose, Jacques, Vapour pressures and excess functions of (3,5; 2,6)dimethylpyridine+n-hexane, n-heptane and n-octane measurement and prediction, Fluid Phase Equilibria, 2005, 232, 1-2, 189-206, https://doi.org/10.1016/j.fluid.2005.03.028 . [all data]

Chickos, Hosseini, et al., 1995
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]

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]

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
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]

Vickers, Kuhn, et al., 2003
Vickers, A.K.; Kuhn, E.; Lautamo, R., A novel, inert, low bleed column for GC-MS, 2003, retrieved from http://www.chem.agilent.com/cag/cabu/gcapps.htm. [all data]

Kuhn, 2001
Kuhn, E.R., Selectivity vs. polarity: the fundamentals of chromatographic separation, J. Sep. Sci., 2001, 24, 6, 473-476, https://doi.org/10.1002/1615-9314(20010601)24:6<473::AID-JSSC473>3.0.CO;2-Y . [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]

Golovnya, Kuz'menko, et al., 2000
Golovnya, R.V.; Kuz'menko, T.E.; Krikunova, N.I., The influence of alkyl substituents on the chromatographic indicator of self-association of N-containing heterocyclic compounds, Russ. Chem. Bull. (Engl. Transl.), 2000, 49, 2, 321-324, https://doi.org/10.1007/BF02494681 . [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]

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]

Golovnya, Samusenko, et al., 1987
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]

Lu, Zhao, et al., 2004
Lu, X.; Zhao, M.; Kong, H.; Cai, J.; Wu, J.; Wu, M.; Hua, R.; Liu, J.; Xu, G., Characterization of cigarette smoke condensates by comprehensive two-dimensional gas chromatography/time-of-flight mass spectrometry (GC x GC/TOFMS) Part 2: Basic fraction, J. Sep. Sci., 2004, 27, 1-2, 101-109, https://doi.org/10.1002/jssc.200301659 . [all data]

Gautzsch and Zinn, 1996
Gautzsch, R.; Zinn, P., Use of incremental models to estimate the retention indexes of aromatic compounds, Chromatographia, 1996, 43, 3/4, 163-176, https://doi.org/10.1007/BF02292946 . [all data]

Golovnya, Samusenko, et al., 1988
Golovnya, R.V.; Samusenko, A.L.; Lyapin, V.A., Prediction of linear temperature programmed retention indices of methylpyridines in capillary gas chromatography, Zh. Anal. Khim., 1988, 63, 2, 311-317. [all data]

Premecz and Ford, 1987
Premecz, J.E.; Ford, M.E., Gas chromatographic separation of substituted pyridines, J. Chromatogr., 1987, 388, 23-35, https://doi.org/10.1016/S0021-9673(01)94463-2 . [all data]

Rostad and Pereira, 1986
Rostad, C.E.; Pereira, W.E., Kovats and Lee retention indices determined by gas chromatography/mass spectrometry for organic compounds of environmental interest, J. Hi. Res. Chromatogr. Chromatogr. Comm., 1986, 9, 6, 328-334, https://doi.org/10.1002/jhrc.1240090603 . [all data]

Lorenz, Stern, et al., 1983
Lorenz, G.; Stern, D.J.; Flath, R.A.; Haddon, W.F.; Tillin, S.J.; Teranishi, R., Identification of sheep liver volatiles, J. Agric. Food Chem., 1983, 31, 5, 1052-1057, https://doi.org/10.1021/jf00119a033 . [all data]

Li, Gao, et al., 2000
Li, R.; Gao, S.-G.; Xiang, B.-R., Using improved BP neural network in predicting GC retention indices, Computers appl. chem. (Chinese), 2000, 17, 1-2, 113-114. [all data]

Kawai, Ishida, et al., 1991
Kawai, T.; Ishida, Y.; Kakiuchi, H.; Ikeda, N.; Higashida, T.; Nakamura, S., Flavor components of dried squid, J. Agric. Food Chem., 1991, 39, 4, 770-777, https://doi.org/10.1021/jf00004a031 . [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]

Baltes and Bochmann, 1987
Baltes, W.; Bochmann, G., Model reactions on roast aroma formations, V. Mass spectrometric identification of pyrifines, oxazoles, and carbocyclic compounds from the reaction of serine and threonine with sucrose under the conditions of coffee roasting, Z. Lebensm. Unters. Forsch., 1987, 185, 1, 5-9, https://doi.org/10.1007/BF01083331 . [all data]

Notes

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

• Symbols used in this document:
  

  Tboil	Boiling point
  Tc	Critical temperature
  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

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