2,6-Lutidine

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

  
• IUPAC Standard InChIKey: OISVCGZHLKNMSJ-UHFFFAOYSA-N Copy
• CAS Registry Number: 108-48-5
• 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: Pyridine, 2,6-dimethyl-; α,α'-Dimethylpyridine; α,α'-Lutidine; 2,6-Dimethylpyridine; 2,6-Dimethypyridine; α,α'-Lutidin; NSC 2155
• 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
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • Ion clustering data
  • References
  • Notes
• Other data available:
  • Henry's Law data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • Gas Chromatography
• Data at other public NIST sites:
  • X-ray Photoelectron Spectroscopy Database, version 5.0
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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 as indicated in comments:
DRB - Donald R. Burgess, Jr.
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

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
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
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) (kcal/mol)
    T_r = reduced temperature (T / T_c)

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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

Reaction 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: Michael M. Meot-Ner (Mautner) and Sharon G. Lias

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. A general reaction search form is also available. Future versions of this site may rely on reaction search pages in place of the enumerated reaction displays seen below.

Individual Reactions

C₇H₁₀N⁺ +  = (C₇H₁₀N⁺ • )

By formula: C₇H₁₀N⁺ + C₇H₉N = (C₇H₁₀N⁺ • C₇H₉N)

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
L - Sharon G. Lias

Data compiled as indicated in comments:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

View reactions leading to C₇H₉N⁺ (ion structure unspecified)

Ionization energy determinations

Ion clustering 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: Michael M. Meot-Ner (Mautner) and Sharon G. Lias

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. Searches may be limited to ion clustering reactions. A general reaction search form is also available.

Clustering reactions

C₇H₁₀N⁺ +  = (C₇H₁₀N⁺ • )

By formula: C₇H₁₀N⁺ + C₇H₉N = (C₇H₁₀N⁺ • C₇H₉N)

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, 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]

Andon, Cox, et al., 1957
Andon, R.J.L.; Cox, J.D.; Herington, E.F.G.; Martin, J.F., The second virial coefficients of pyridine and benzene, and certain of their methyl homologues, Trans. Faraday Soc., 1957, 53, 1074. [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]

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

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

Lipkind and Chickos, 2009
Lipkind, Dmitri; Chickos, James S., An examination of the vaporization enthalpies and vapor pressures of pyrazine, pyrimidine, pyridazine, and 1,3,5-triazine, Struct Chem, 2009, 20, 1, 49-58, https://doi.org/10.1007/s11224-008-9389-5 . [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]

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]

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]

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]

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]

Meot-Ner M. and Sieck, 1983
Meot-Ner M.; Sieck, L.W., The Ionic Hydrogen Bond. 1. Sterically Hindered Bonds. Solvation and Clustering of Sterically Hindered Amines and Pyridines, J. Am. Chem. Soc., 1983, 105, 10, 2956, https://doi.org/10.1021/ja00348a005 . [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]

Utsunomiya, Kobayashi, et al., 1978
Utsunomiya, C.; Kobayashi, T.; Nagakura, S., Photoelectron angular distribution measurements for some pyridines, Bull. Chem. Soc. Jpn., 1978, 451, 3482. [all data]

Distefano, Foffani, et al., 1971
Distefano, G.; Foffani, A.; Innorta, G.; Pignataro, S., Mass spectrometric study of transition metal complexes with ligands having nitrogen or sulphur as donor atom, Adv. Mass Spectrom., 1971, 5, 696. [all data]

Distefano, Foffani, et al., 1971, 2
Distefano, G.; Foffani, A.; Innorta, G.; Pignataro, S., Electron impact ionization potentials of some manganese, chromium and tungsten organometallic derivatives, Int. J. Mass Spectrom. Ion Phys., 1971, 7, 383. [all data]

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

Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, References

• Symbols used in this document:
  

  Cp,liquid	Constant pressure heat capacity of liquid
  IE (evaluated)	Recommended ionization energy
  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
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔrS°	Entropy of reaction at standard conditions
  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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