Pyridine, 3,4-dimethyl-

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

  
• IUPAC Standard InChIKey: NURQLCJSMXZBPC-UHFFFAOYSA-N Copy
• CAS Registry Number: 583-58-4
• 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.
• Other names: 3,4-Lutidine; 3,4-Dimethylpyridine; 3,4-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
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
  • Gas Chromatography
  • References
  • Notes
• Other data available:
  • Henry's Law data
  • Gas phase ion energetics data
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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
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos
DH - Eugene S. Domalski and Elizabeth D. Hearing

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

Temperature of phase transition

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

• SOLUTION (10% CCl4 FOR 3800-1330, 10% CS2 FOR 1330-450 CM^-1) $$ STRUCTURE VERIFIED BY SOLUTION SPECTRUM FROM ROY WARD, BRITISH PETROLEUM CHEMICALS INTERNATIONAL, LTD.; DOW KBr FOREPRISM-GRATING; DIGITIZED BY COBLENTZ SOCIETY (BATCH I) FROM HARD COPY; 2 cm^-1 resolution
• SOLUTION (10% CCl4 FOR 5000-1330, 10% CS2 FOR 1330-625 CM^-1) $$ SALT ADDED TO BOTH SOLUTIONS; Not specified, most likely a prism, grating, or hybrid spectrometer.; DIGITIZED BY NIST FROM HARD COPY; 4 cm^-1 resolution
• VAPOR (0.5 MICROLITER AT 150 C); NICOLET FTIR; DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 4 CM^-1 cm^-1 resolution

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, custom temperature program

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Lee's RI, non-polar column, temperature ramp

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References

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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]

Podoski, Rachwalska, et al., 1984
Podoski, T.; Rachwalska, M.; Mayer, J., The study of specific heat of liquid 3,4-dimethylpyridine by the adiabatic calorimetry method, Physica B (Amsterdam), 1984, 125(2), 215-218. [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]

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]

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]

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]

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]

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]

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]

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]

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]

Kim, 2001
Kim, J.S., Einfluss der Temperatur beim Rösten von Sesam auf Aroma und antioxidative Eigenschaften des Öls, PhD Thesis, Technischen Universität Berlin zur Erlangung des akademischen Grades, Berlin, 2001, 151. [all data]

Kubec, Drhová, et al., 1999
Kubec, R.; Drhová, V.; Velísek, J., Volatile compounds thermally generated from S-propylcysteine and S-propylcysteine sulfoxide - aroma precursors of Allium vegetables, J. Agric. Food Chem., 1999, 47, 3, 1132-1138, https://doi.org/10.1021/jf980974z . [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]

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, Condensed phase thermochemistry data, Phase change 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
  Ttrs	Temperature of phase transition
  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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