Pyridine, 3,5-dimethyl-

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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.

Quantity Value Units Method Reference Comment
Δfgas72.8kJ/molN/ACox and Gundry, 1958Value computed using ΔfHliquid° value of 22.4 kj/mol from Cox and Gundry, 1958 and ΔvapH° value of 50.38 kj/mol from missing citation.

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

Quantity Value Units Method Reference Comment
Δfliquid22.4kJ/molCcbCox and Gundry, 1958ALS
Quantity Value Units Method Reference Comment
Δcliquid-4063.2kJ/molCcbCox and Gundry, 1958ALS
Quantity Value Units Method Reference Comment
liquid241.72J/mol*KN/ASteele, Chirico, et al., 1986DH

Constant pressure heat capacity of liquid

Cp,liquid (J/mol*K) Temperature (K) Reference Comment
184.55298.15Steele, Chirico, et al., 1986T = 10 to 450 K.; DH

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

Quantity Value Units Method Reference Comment
Tboil442.7KN/AAldrich Chemical Company Inc., 1990BS
Tboil444.8KN/AWeast and Grasselli, 1989BS
Tboil445.1KN/AMajer and Svoboda, 1985 
Tboil444.6KN/AJankun-Pinska, 1965Uncertainty assigned by TRC = 0.5 K; TRC
Quantity Value Units Method Reference Comment
Tfus266.823KN/ASteele, Chirico, et al., 1986DH
Tfus266.85KN/AKyte, Jeffery, et al., 1960Uncertainty assigned by TRC = 0.3 K; TRC
Tfus266.65KN/ACoulson, Cox, et al., 1959Uncertainty assigned by TRC = 0.02 K; TRC
Quantity Value Units Method Reference Comment
Ttriple266.81KN/AChirico, Hossenlopp, et al., 1994Uncertainty assigned by TRC = 0.01 K; TRC
Quantity Value Units Method Reference Comment
Tc667.2KN/AMajer and Svoboda, 1985 
Tc667.25KN/AAmbrose, Cox, et al., 1960Uncertainty assigned by TRC = 0.3 K; Visual, PRT, IPTS-48; TRC
Tc667.25KN/ACox, 1960Uncertainty assigned by TRC = 1. K; measured by R. Townsend to be pub. later; TRC
Quantity Value Units Method Reference Comment
Δvap49.49kJ/molN/AMajer and Svoboda, 1985 
Δvap48.5kJ/molN/ABen-makhlouf-Hakem, Ait-Kaci, et al., 2005Based on data from 273. to 353. K.; AC
Δvap48.7kJ/molCGCChickos, Hosseini, et al., 1995Based on data from 323. to 373. K.; AC
Δvap50.38kJ/molVCox, 1960ALS

Enthalpy of vaporization

ΔvapH (kJ/mol) Temperature (K) Method Reference Comment
39.46445.1N/AMajer and Svoboda, 1985 
47.0340.N/ASakoguchi, Ueoka, et al., 1995Based on data from 288. to 392. K.; AC
46.7340.EBSteele, Chirico, et al., 1995Based on data from 335. to 487. K.; AC
44.3380.EBSteele, Chirico, et al., 1995Based on data from 335. to 487. K.; AC
41.8420.EBSteele, Chirico, et al., 1995Based on data from 335. to 487. K.; AC
39.2460.EBSteele, Chirico, et al., 1995Based on data from 335. to 487. K.; AC
44.3388.AStephenson and Malanowski, 1987Based on data from 373. to 446. K. See also Kkykj and Repas, 1973.; AC
49.1288.MMWisniewska, Lencka, et al., 1986Based on data from 273. to 358. K.; AC
49.6313.CMajer, Svoboda, et al., 1985AC
46.5343.CMajer, Svoboda, et al., 1985AC
44.8368.CMajer, Svoboda, et al., 1985AC

Enthalpy of vaporization

ΔvapH = A exp(-βTr) (1 − Tr)β
    ΔvapH = Enthalpy of vaporization (at saturation pressure) (kJ/mol)
    Tr = reduced temperature (T / Tc)

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Temperature (K) A (kJ/mol) β Tc (K) Reference Comment
313. to 368.68.350.311667.2Majer and Svoboda, 1985 

Antoine Equation Parameters

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

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Temperature (K) A B C Reference Comment
436.00 to 445.884.372241716.267-52.008Coulson, Cox, et al., 1959, 2Coefficents calculated by NIST from author's data.

Enthalpy of fusion

ΔfusH (kJ/mol) Temperature (K) Reference Comment
13.11266.9Chirico, Hossenlopp, et al., 1994, 2AC

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:


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)

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

H (mol/(kg*bar)) d(ln(kH))/d(1/T) (K) Method Reference
140.6800.MN/A

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)

Quantity Value Units Method Reference Comment
Proton affinity (review)955.4kJ/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity923.5kJ/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
9.25PERamsey and Walker, 1974Vertical value; LLK

Mass spectrum (electron ionization)

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Henry's Law data, Gas phase ion energetics data, 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: NIST Mass Spectrometry Data Center, William E. Wallace, director

Spectrum

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Mass spectrum
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Additional Data

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Owner NIST Mass Spectrometry Data Center
Collection (C) 2014 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin Japan AIST/NIMC Database- Spectrum MS-NW- 712
NIST MS number 227863

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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), 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]

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]

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]

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]

Ramsey and Walker, 1974
Ramsey, B.G.; Walker, F.A., A linear relationship between substituted pyridine lone pair vertical ionization potentials and pKa, J. Am. Chem. Soc., 1974, 96, 3314. [all data]


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), References