Pyridine, 3-methyl-

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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:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.

Quantity Value Units Method Reference Comment
Δfgas103.6 ± 1.3kJ/molCcbGerasimov, Gubareva, et al., 1992%hf298_condensed[kJ/mol]=-61.1±1.3; ALS
Δfgas106.1 ± 0.71kJ/molCcbScott, Good, et al., 1963ALS
Δfgas113.6 ± 1.0kJ/molCmAndon, Cox, et al., 1957ALS
Δfgas113.6 ± 1.0kJ/molCcbCox, Challoner, et al., 1954ALS
Δfgas75.5kJ/molN/AConstam and White, 1903Value computed using ΔfHliquid° value of 33.0 kj/mol from Constam and White, 1903 and ΔvapH° value of 42.5 kj/mol from Gerasimov, Gubareva, et al., 1992.; DRB

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
Δfliquid61.1 ± 1.3kJ/molCcbGerasimov, Gubareva, et al., 1992%hf298_condensed[kJ/mol]=-61.1±1.3; ALS
Δfliquid61.71 ± 0.59kJ/molCcbScott, Good, et al., 1963ALS
Δfliquid68.3 ± 1.0kJ/molCcbCox, Challoner, et al., 1954ALS
Δfliquid33.kJ/molCcbConstam and White, 1903ALS
Quantity Value Units Method Reference Comment
Δcliquid-3300.4 ± 1.3kJ/molCcbGerasimov, Gubareva, et al., 1992%hf298_condensed[kJ/mol]=-61.1±1.3; ALS
Δcliquid-3423.2 ± 0.50kJ/molCcbScott, Good, et al., 1963ALS
Δcliquid-3429.8 ± 1.0kJ/molCcbCox, Challoner, et al., 1954ALS
Δcliquid-3402.kJ/molCcbConstam and White, 1903ALS
Quantity Value Units Method Reference Comment
liquid216.31J/mol*KN/AScott, Good, et al., 1963DH

Constant pressure heat capacity of liquid

Cp,liquid (J/mol*K) Temperature (K) Reference Comment
158.69298.15Scott, Good, et al., 1963T = 12 to 400 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
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
Tboil417.0 ± 0.7KAVGN/AAverage of 20 out of 22 values; Individual data points
Quantity Value Units Method Reference Comment
Tfus255. ± 2.KAVGN/AAverage of 8 values; Individual data points
Quantity Value Units Method Reference Comment
Ttriple255.010KN/AScott, Good, et al., 1963, 2Uncertainty assigned by TRC = 0.06 K; by extrapolation of 1/f, from calorimeter, to zero; TRC
Quantity Value Units Method Reference Comment
Tc645.KN/AMajer and Svoboda, 1985 
Tc644.85KN/AAmbrose and Grant, 1957Uncertainty assigned by TRC = 0.5 K; TRC
Quantity Value Units Method Reference Comment
Δvap44. ± 2.kJ/molAVGN/AAverage of 10 values; Individual data points

Enthalpy of vaporization

ΔvapH (kJ/mol) Temperature (K) Method Reference Comment
37.35417.3N/AMajer and Svoboda, 1985 
43.2 ± 0.1320.EBChirico, Knipmeyer, et al., 1999Based on data from 314. to 457. K.; AC
40.9 ± 0.1360.EBChirico, Knipmeyer, et al., 1999Based on data from 314. to 457. K.; AC
38.6 ± 0.1400.EBChirico, Knipmeyer, et al., 1999Based on data from 314. to 457. K.; AC
36.1 ± 0.2440.EBChirico, Knipmeyer, et al., 1999Based on data from 314. to 457. K.; AC
40.1389.AStephenson and Malanowski, 1987Based on data from 374. to 458. K.; AC
37.7465.AStephenson and Malanowski, 1987Based on data from 450. to 570. K.; AC
36.8576.AStephenson and Malanowski, 1987Based on data from 561. to 645. K.; AC
41.3362.EB,IPStephenson and Malanowski, 1987Based on data from 347. to 458. K. See also Osborn and Douslin, 1968.; AC
41.3362.EBStephenson and Malanowski, 1987Based on data from 347. to 458. K. See also Scott, Good, et al., 1963.; AC
43.6 ± 0.1313.CMajer, Svoboda, et al., 1984AC
42.7 ± 0.1328.CMajer, Svoboda, et al., 1984AC
42.0 ± 0.1343.CMajer, Svoboda, et al., 1984AC
40.4 ± 0.1368.CMajer, Svoboda, et al., 1984AC
40.2 ± 0.1372.CScott, Good, et al., 1963AC
38.9 ± 0.1393.CScott, Good, et al., 1963AC
37.4 ± 0.1417.CScott, Good, et al., 1963AC
41.0369.MGHerington and Martin, 1953Based on data from 354. to 418. K.; AC

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
298. to 417.61.060.2913645.Majer 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
347.19 to 457.724.178791484.307-61.606Osborn and Douslin, 1968

Enthalpy of sublimation

ΔsubH (kJ/mol) Temperature (K) Reference Comment
62.2240.Stephenson and Malanowski, 1987Based on data from 225. to 255. K.; AC

Enthalpy of fusion

ΔfusH (kJ/mol) Temperature (K) Reference Comment
14.180255.01Scott, Good, et al., 1963DH
14.18255.Domalski and Hearing, 1996AC

Entropy of fusion

ΔfusS (J/mol*K) Temperature (K) Reference Comment
55.61255.01Scott, Good, et al., 1963DH

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

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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:
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, 3-methyl-

By formula: C6H6N- + H+ = C6H7N

Quantity Value Units Method Reference Comment
Δr1581. ± 13.kJ/molG+TSDePuy, Kass, et al., 1988gas phase; Acid: 3-methylpyridine. Comparable to EtOH.; B
Quantity Value Units Method Reference Comment
Δr1552. ± 13.kJ/molIMRBDePuy, Kass, et al., 1988gas phase; Acid: 3-methylpyridine. Comparable to EtOH.; B

Lithium ion (1+) + Pyridine, 3-methyl- = (Lithium ion (1+) • Pyridine, 3-methyl-)

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

Quantity Value Units Method Reference Comment
Δr197. ± 15.kJ/molCIDTRodgers, 2001RCD

Sodium ion (1+) + Pyridine, 3-methyl- = (Sodium ion (1+) • Pyridine, 3-methyl-)

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

Quantity Value Units Method Reference Comment
Δr133. ± 4.2kJ/molCIDTRodgers, 2001RCD

Potassium ion (1+) + Pyridine, 3-methyl- = (Potassium ion (1+) • Pyridine, 3-methyl-)

By formula: K+ + C6H7N = (K+ • C6H7N)

Quantity Value Units Method Reference Comment
Δr100. ± 3.kJ/molCIDTRodgers, 2001RCD

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 Comment
54. QN/A missing citation give several references for the Henry's law constants but don't assign them to specific species.
130.6400.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
L - Sharon G. Lias

Data compiled as indicated in comments:
B - John E. Bartmess
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 C6H7N+ (ion structure unspecified)

Quantity Value Units Method Reference Comment
IE (evaluated)9.0eVN/AN/AL
Quantity Value Units Method Reference Comment
Proton affinity (review)943.4kJ/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity911.6kJ/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
8.9PEModelli and Distefano, 1981LLK
9.43 ± 0.05EIZaretskii, Oren, et al., 1976LLK
9.4 ± 0.1EIStefanovic and Grutzmacher, 1974LLK
9.04 ± 0.03PIWatanabe, Nakayama, et al., 1962RDSH
9.3PEModelli and Distefano, 1981Vertical value; LLK
9.31PEKimura, Katsumata, et al., 1981Vertical value; LLK
9.29PEKlasinc, Novak, et al., 1978Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C5H6+12.94 ± 0.05HCNEIZaretskii, Oren, et al., 1976LLK
C6H6N+12.3 ± 0.1HEIPalmer and Lossing, 1963RDSH

De-protonation reactions

C6H6N- + Hydrogen cation = Pyridine, 3-methyl-

By formula: C6H6N- + H+ = C6H7N

Quantity Value Units Method Reference Comment
Δr1581. ± 13.kJ/molG+TSDePuy, Kass, et al., 1988gas phase; Acid: 3-methylpyridine. Comparable to EtOH.; B
Quantity Value Units Method Reference Comment
Δr1552. ± 13.kJ/molIMRBDePuy, Kass, et al., 1988gas phase; Acid: 3-methylpyridine. Comparable to EtOH.; B

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

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


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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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-5548
NIST MS number 228545

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.


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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UVVis spectrum
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Additional Data

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Source Coulson and Ditcham, 1952
Owner INEP CP RAS, NIST OSRD
Collection (C) 2007 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin INSTITUTE OF ENERGY PROBLEMS OF CHEMICAL PHYSICS, RAS
Source reference RAS UV No. 12161
Instrument n.i.g.
Melting point - 18.1
Boiling point 144.1

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Gerasimov, Gubareva, et al., 1992
Gerasimov, P.A.; Gubareva, A.I.; Tarbeeva, N.A.; Kunderenko, V.M., Physicochemical characteristics of β-picoline, J. Appl. Chem. USSR, 1992, 65, 388-390. [all data]

Scott, Good, et al., 1963
Scott, D.W.; Good, W.D.; Guthrie, G.B.; Todd, S.S.; Hossenlopp, I.A.; Osborn, A.G.; McCullough, J.P., Chemical thermodynamic properties and internal rotation of methylpyridines. II. 3-methylpyridine, J. Phys. Chem., 1963, 67, 685-689. [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]

Scott, Good, et al., 1963, 2
Scott, D.W.; Good, W.D.; Guthrie, G.B.; Todd, S.S.; Hossenlopp, I.A.; Osborn, A.G.; McCullough, J.P., Chemical Thermodynamic Properties and Internal Rotation of Methylpyridines II. 3-Methylpyridine, J. Phys. Chem., 1963, 67, 685. [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]

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]

Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D., Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III, J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985 . [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]

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]

Modelli and Distefano, 1981
Modelli, A.; Distefano, G., He(I) photoelectron spectra of chloro-, vinyl- and acetyl-pyridines, J. Electron Spectrosc. Relat. Phenom., 1981, 23, 323. [all data]

Zaretskii, Oren, et al., 1976
Zaretskii, Z.V.I.; Oren, D.; Kelner, L., Automatic method for the measurement of the electron impact ionization and appearance potentials, Appl. Spectrosc., 1976, 30, 366. [all data]

Stefanovic and Grutzmacher, 1974
Stefanovic, D.; Grutzmacher, H.F., The ionisation potential of some substituted pyridines, Org. Mass Spectrom., 1974, 9, 1052. [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]

Kimura, Katsumata, et al., 1981
Kimura, K.; Katsumata, S.; Achiba, Y.; Yamazaki, T.; Iwata, S., Ionization energies, Ab initio assignments, and valence electronic structure for 200 molecules in Handbook of HeI Photoelectron Spectra of Fundamental Organic Compounds, Japan Scientific Soc. Press, Tokyo, 1981. [all data]

Klasinc, Novak, et al., 1978
Klasinc, L.; Novak, I.; Scholz, M.; Kluge, G., Photoelektronenspektren substituierter Pyridine und Benzole und ihre Interpretation durch die CNDO/SWW-Methode, Croat. Chem. Acta, 1978, 51, 43. [all data]

Palmer and Lossing, 1963
Palmer, T.F.; Lossing, F.P., Free radicals by mass spectrometry. XXX. Ionization potentials of anilino and 2-, 3-, and 4-pyridylmethyl radicals, J. Am. Chem. Soc., 1963, 85, 1733. [all data]

Coulson and Ditcham, 1952
Coulson, E.A.; Ditcham, J.B., J. Appli. Chem. (London), 1952, 2, 71. [all data]


Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, References