Home Symbol which looks like a small house Up Solid circle with an upward pointer in it

Pyridine, 4-methyl-

Data at NIST subscription sites:

NIST subscription sites provide data under the NIST Standard Reference Data Program, but require an annual fee to access. The purpose of the fee is to recover costs associated with the development of data collections included in such sites. Your institution may already be a subscriber. Follow the links above to find out more about the data in these sites and their terms of usage.


Gas phase thermochemistry data

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), References, Notes

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
DRB - Donald R. Burgess, Jr.

Quantity Value Units Method Reference Comment
Deltafgas24.80 ± 0.22kcal/molCcbGood, 1972ALS
Deltafgas24.41 ± 0.15kcal/molCmAndon, Cox, et al., 1957ALS
Deltafgas24.43 ± 0.15kcal/molCcbCox, Challoner, et al., 1954ALS
Deltafgas22.2kcal/molN/AConstam and White, 1903Value computed using «DELTA»fHliquid° value of 48.1 kj/mol from Constam and White, 1903 and «DELTA»vapH° value of 44.6 kj/mol from Good, 1972.; DRB

Condensed phase thermochemistry data

Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), References, Notes

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
Deltafliquid14.15 ± 0.21kcal/molCcbGood, 1972ALS
Deltafliquid13.57 ± 0.15kcal/molCcbCox, Challoner, et al., 1954ALS
Deltafliquid11.49kcal/molCcbConstam and White, 1903ALS
Quantity Value Units Method Reference Comment
Deltacliquid-817.56 ± 0.20kcal/molCcbGood, 1972ALS
Deltacliquid-816.99 ± 0.15kcal/molCcbCox, Challoner, et al., 1954ALS
Deltacliquid-816.7kcal/molCcbConstam and White, 1903ALS
Quantity Value Units Method Reference Comment
liquid49.9739cal/mol*KN/AMesserly, Todd, et al., 1988DH
liquid49.766cal/mol*KN/AMesserly, Todd, et al., 1987DH
liquid49.766cal/mol*KN/ASteele, Chirico, et al., 1986DH

Constant pressure heat capacity of liquid

Cp,liquid (cal/mol*K) Temperature (K) Reference Comment
37.9990298.150Messerly, Todd, et al., 1988T = 10 to 400 K.; DH
38.000298.15Messerly, Todd, et al., 1987T = 10 to 410 K.; DH
38.000298.15Steele, Chirico, et al., 1986T = 10 to 410 K.; DH

Phase change data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), References, Notes

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
DRB - Donald R. Burgess, Jr.
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity Value Units Method Reference Comment
Tboil418. ± 1.KAVGN/AAverage of 19 values; Individual data points
Quantity Value Units Method Reference Comment
Tfus276.8 ± 0.8KAVGN/AAverage of 10 values; Individual data points
Quantity Value Units Method Reference Comment
Ttriple276.800KN/AMesserly, Todd, et al., 1988, 2Crystal phase 1 phase; Uncertainty assigned by TRC = 0.03 K; TRC
Ttriple276.810KN/AMesserly, Todd, et al., 1988, 2Crystal phase 1 phase; Uncertainty assigned by TRC = 0.02 K; TRC
Ttriple276.8KN/ASoulard, Fillaux, et al., 1986Crystal phase 1 phase; Uncertainty assigned by TRC = 1. K; phases identified by Raman spectrum; TRC
Quantity Value Units Method Reference Comment
Tc646.KN/AMajer and Svoboda, 1985 
Tc646.3KN/AKobe and Mathews, 1970Uncertainty assigned by TRC = 0.5 K; TRC
Tc645.65KN/AAmbrose and Grant, 1957Uncertainty assigned by TRC = 0.5 K; TRC
Quantity Value Units Method Reference Comment
Pc45.99atmN/AKobe and Mathews, 1970Uncertainty assigned by TRC = 0.5000 atm; TRC
Quantity Value Units Method Reference Comment
rhoc3.07mol/lN/AKobe and Mathews, 1970Uncertainty assigned by TRC = 0.21 mol/l; TRC
Quantity Value Units Method Reference Comment
Deltavap10.7 ± 0.1kcal/molAVGN/AAverage of 9 values; Individual data points

Enthalpy of vaporization

DeltavapH (kcal/mol) Temperature (K) Method Reference Comment
8.965418.5N/AMajer and Svoboda, 1985 
10.4 ± 0.02320.EBChirico, Knipmeyer, et al., 1999Based on data from 328. - 459. K.; AC
9.82 ± 0.02360.EBChirico, Knipmeyer, et al., 1999Based on data from 328. - 459. K.; AC
9.27 ± 0.02400.EBChirico, Knipmeyer, et al., 1999Based on data from 328. - 459. K.; AC
8.65 ± 0.05440.EBChirico, Knipmeyer, et al., 1999Based on data from 328. - 459. K.; AC
9.89363.AStephenson and Malanowski, 1987Based on data from 348. - 460. K.; AC
10.1347.AStephenson and Malanowski, 1987Based on data from 348. - 347. K.; AC
9.56396.AStephenson and Malanowski, 1987Based on data from 381. - 460. K.; AC
9.06467.AStephenson and Malanowski, 1987Based on data from 452. - 573. K.; AC
8.89579.AStephenson and Malanowski, 1987Based on data from 564. - 646. K.; AC
9.89363.EB,IPStephenson and Malanowski, 1987Based on data from 348. - 459. K. See also Osborn and Douslin, 1968.; AC
10.5 ± 0.02313.CMajer, Svoboda, et al., 1984AC
10.3 ± 0.02328.CMajer, Svoboda, et al., 1984AC
10.1 ± 0.02343.CMajer, Svoboda, et al., 1984AC
9.87365.MGHerington and Martin, 1953Based on data from 350. - 418. K.; AC

Enthalpy of vaporization

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

View plot Requires a JavaScript / HTML 5 canvas capable browser.

Temperature (K) 298. - 434.
A (kcal/mol) 15.3
alpha 0.5241
beta 0.1879
Tc (K) 646.
ReferenceMajer and Svoboda, 1985

Antoine Equation Parameters

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

View plot Requires a JavaScript / HTML 5 canvas capable browser.

Temperature (K) A B C Reference Comment
348.20 - 459.074.16411482.84-62.407Osborn and Douslin, 1968 
350.06 - 418.614.166671484.484-62.229Herington and Martin, 1953, 2Coefficents calculated by NIST from author's data.

Enthalpy of sublimation

DeltasubH (kcal/mol) Temperature (K) Method Reference Comment
15.0226.AStephenson and Malanowski, 1987Based on data from 213. - 239. K.; AC

Temperature of phase transition

Ttrs (K) Initial Phase Final Phase Reference Comment
255.010crystaline, IIcrystaline, ISteele, Chirico, et al., 1986DH
276.818crystaline, IliquidSteele, Chirico, et al., 1986DH

Enthalpy of phase transition

DeltaHtrs (kcal/mol) Temperature (K) Initial Phase Final Phase Reference Comment
0.00255.00crystaline, IIcrystaline, IMesserly, Todd, et al., 1988DH
3.007238276.818crystaline, IliquidMesserly, Todd, et al., 1988DH
0.000020255.010crystaline, IIcrystaline, IMesserly, Todd, et al., 1987DH
3.0060276.817crystaline, IliquidMesserly, Todd, et al., 1987DH

Entropy of phase transition

DeltaStrs (cal/mol*K) Temperature (K) Initial Phase Final Phase Reference Comment
10.86276.818crystaline, IliquidMesserly, Todd, et al., 1988DH
10.86276.817crystaline, IliquidMesserly, Todd, et al., 1987DH

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:


Reaction thermochemistry data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, IR Spectrum, Mass spectrum (electron ionization), References, Notes

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:
B - John E. Bartmess
RCD - Robert C. Dunbar

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

C6H6N- + Hydrogen cation = Pyridine, 4-methyl-

By formula: C6H6N- + H+ = C6H7N

Quantity Value Units Method Reference Comment
Deltar369.7 ± 5.1kcal/molG+TSMeot-ner and Kafafi, 1988gas phase; anchored to 88MEO scale, not the "87 acidity scale". The Kiefer, Zhang, et al., 1997 BDE is for ortho.; B
Deltar374.8 ± 3.1kcal/molG+TSDePuy, Kass, et al., 1988gas phase; Acid: p-methylpyridine. Between iPrOH, MeCN.; B
Quantity Value Units Method Reference Comment
Deltar362.9 ± 5.0kcal/molIMRBMeot-ner and Kafafi, 1988gas phase; anchored to 88MEO scale, not the "87 acidity scale". The Kiefer, Zhang, et al., 1997 BDE is for ortho.; B
Deltar368.0 ± 3.0kcal/molIMRBDePuy, Kass, et al., 1988gas phase; Acid: p-methylpyridine. Between iPrOH, MeCN.; B

Lithium ion (1+) + Pyridine, 4-methyl- = (Lithium ion (1+) bullet Pyridine, 4-methyl-)

By formula: Li+ + C6H7N = (Li+ bullet C6H7N)

Quantity Value Units Method Reference Comment
Deltar46.9 ± 3.3kcal/molCIDTRodgers, 2001RCD

Sodium ion (1+) + Pyridine, 4-methyl- = (Sodium ion (1+) bullet Pyridine, 4-methyl-)

By formula: Na+ + C6H7N = (Na+ bullet C6H7N)

Quantity Value Units Method Reference Comment
Deltar31.9 ± 0.9kcal/molCIDTRodgers, 2001RCD

Potassium ion (1+) + Pyridine, 4-methyl- = (Potassium ion (1+) bullet Pyridine, 4-methyl-)

By formula: K+ + C6H7N = (K+ bullet C6H7N)

Quantity Value Units Method Reference Comment
Deltar23.6 ± 1.0kcal/molCIDTRodgers, 2001RCD

IR Spectrum

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

Data compiled by: Coblentz Society, Inc.

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


Mass spectrum (electron ionization)

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, 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

Notice: This spectrum may be better viewed with a Javascript and HTML 5 enabled browser.

Mass spectrum
For Zoom
1.) Enter the desired X axis range (e.g., 100, 200)
2.) Check here for automatic Y scaling
3.) Press here to zoom

Additional Data

View image of digitized spectrum (can be printed in landscape orientation).

View spectrum image in SVG format.

Download spectrum in JCAMP-DX format.

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- 779
NIST MS number 228749

All mass spectra in this site (plus many more) are available from the NIST/EPA/NIH Mass Spectral Library. Please see the following for information about the library and its accompanying search program.


References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, 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.

Good, 1972
Good, W.D., Enthalpies of combustion of nine organic nitrogen compounds related to petroleum, J. Chem. Eng. Data, 1972, 17, 28-31. [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]

Constam and White, 1903
Constam, E.J.; White, J., Physico-chemical investigations in the pyridine series, Am. Chem. J., 1903, 29, 1-49. [all data]

Messerly, Todd, et al., 1988
Messerly, J.F.; Todd, S.S.; Finke, H.L.; Good, W.D.; Gammon, B.E., Condensed-phase heat-capacity studies and derived thermodynamic properties for six cyclic nitrogen compounds, J. Chem. Thermodynam., 1988, 20, 209-224. [all data]

Messerly, Todd, et al., 1987
Messerly, J.F.; Todd, S.S.; Finke, H.L.; Gammon, B.E., Thermodynamic properties of organic nitrogen compounds that occur in shale oil and heavy petroleum-topical report, NIPER Report, 1987, 83, 37p. [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]

Messerly, Todd, et al., 1988, 2
Messerly, J.F.; Todd, s.S.; Finke, H.L.; Good, W.D.; Gammon, B.E., Condensed-phase heat-capacity studies and derived thermodynamic properties for six cyclic nitrogen compounds, J. Chem. Thermodyn., 1988, 20, 209. [all data]

Soulard, Fillaux, et al., 1986
Soulard, L.; Fillaux, F.; Braathen, G.; Le Calve, N.; Pasquier, B., Rotational Dynamics of the Methyl Group in the 4-Methyl pyridine Crystal, Chem. Phys. Lett., 1986, 125, 41. [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]

Kobe and Mathews, 1970
Kobe, K.A.; Mathews, J.F., Critical Properties and Vapor Pressures of Some Organic Nitrogen and Oxygen Compounds, J. Chem. Eng. Data, 1970, 15, 182. [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]

Chirico, Knipmeyer, et al., 1999
Chirico, R.D.; Knipmeyer, S.E.; Nguyen, A.; Steele, W.V., Thermodynamic properties of the methylpyridines. Part 2. Vapor pressures, heat capacities, critical properties, derived thermodynamic functions between the temperatures 250 K and 560 K, and equilibrium isomer distributions for all temperatures >=250 K, The Journal of Chemical Thermodynamics, 1999, 31, 3, 339-378, https://doi.org/10.1006/jcht.1998.0451 . [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]

Osborn and Douslin, 1968
Osborn, Ann G.; Douslin, Donald R., Vapor pressure relations of 13 nitrogen compounds related to petroleum, J. Chem. Eng. Data, 1968, 13, 4, 534-537, https://doi.org/10.1021/je60039a024 . [all data]

Majer, Svoboda, et al., 1984
Majer, V.; Svoboda, V.; Lencka, M., Enthalpies of vaporization and cohesive energies of pyridine and isomeric methylpyridines, J. Chem. Thermodyn., 1984, 16, 1019-1024. [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]

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]

Meot-ner and Kafafi, 1988
Meot-ner, M.; Kafafi, S.A., Carbon Acidities of Aromatic Compounds, J. Am. Chem. Soc., 1988, 110, 19, 6297, https://doi.org/10.1021/ja00227a003 . [all data]

Kiefer, Zhang, et al., 1997
Kiefer, J.H.; Zhang, Q.; Kern, R.D.; Yao, J.; Jursic, B., Pyrolysis of Aromatic Azines: Pyrazine, Pyrimidine, and Pyridine, J. Phys. Chem. A, 1997, 101, 38, 7061, https://doi.org/10.1021/jp970211z . [all data]

DePuy, Kass, et al., 1988
DePuy, C.H.; Kass, S.R.; Bean, G.P., Formation and Reactions of Heteroaromatic Anions in the Gas Phase, J. Org. Chem., 1988, 53, 19, 4427, https://doi.org/10.1021/jo00254a001 . [all data]

Rodgers, 2001
Rodgers, M.T., Substituent Effects in the Binding of Alkali Metal Ions to Pyridines, Studied by Threshold Collision-Induced Dissociation and ab Initio Theory: The Methylpyridines, J. Phys. Chem. A, 2001, 105, 11, 2374, https://doi.org/10.1021/jp004055z . [all data]


Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), References