Pyridine, 4-methyl-
- Formula: C6H7N
- Molecular weight: 93.1265
- IUPAC Standard InChIKey: FKNQCJSGGFJEIZ-UHFFFAOYSA-N
- CAS Registry Number: 108-89-4
- 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: 4-Picoline; γ-Methylpyridine; γ-Picoline; p-Methylpyridine; p-Picoline; Ba 35846; 4-Methylpyridine; para-Methylpyridine; gamma-Picoline; NSC 18252
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Condensed phase thermochemistry data
Go To: Top, Phase change 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 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 |
---|---|---|---|---|---|
ΔfH°liquid | 14.15 ± 0.21 | kcal/mol | Ccb | Good, 1972 | ALS |
ΔfH°liquid | 13.57 ± 0.15 | kcal/mol | Ccb | Cox, Challoner, et al., 1954 | ALS |
ΔfH°liquid | 11.49 | kcal/mol | Ccb | Constam and White, 1903 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -817.56 ± 0.20 | kcal/mol | Ccb | Good, 1972 | ALS |
ΔcH°liquid | -816.99 ± 0.15 | kcal/mol | Ccb | Cox, Challoner, et al., 1954 | ALS |
ΔcH°liquid | -816.7 | kcal/mol | Ccb | Constam and White, 1903 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°liquid | 49.9739 | cal/mol*K | N/A | Messerly, Todd, et al., 1988 | DH |
S°liquid | 49.766 | cal/mol*K | N/A | Messerly, Todd, et al., 1987 | DH |
S°liquid | 49.766 | cal/mol*K | N/A | Steele, Chirico, et al., 1986 | DH |
Constant pressure heat capacity of liquid
Cp,liquid (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
37.9990 | 298.150 | Messerly, Todd, et al., 1988 | T = 10 to 400 K.; DH |
38.000 | 298.15 | Messerly, Todd, et al., 1987 | T = 10 to 410 K.; DH |
38.000 | 298.15 | Steele, Chirico, et al., 1986 | T = 10 to 410 K.; DH |
Phase change data
Go To: Top, Condensed phase thermochemistry 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 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 |
---|---|---|---|---|---|
Tboil | 418. ± 1. | K | AVG | N/A | Average of 18 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 276.8 ± 0.8 | K | AVG | N/A | Average of 9 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 276.800 | K | N/A | Messerly, Todd, et al., 1988, 2 | Crystal phase 1 phase; Uncertainty assigned by TRC = 0.03 K; TRC |
Ttriple | 276.810 | K | N/A | Messerly, Todd, et al., 1988, 2 | Crystal phase 1 phase; Uncertainty assigned by TRC = 0.02 K; TRC |
Ttriple | 276.8 | K | N/A | Soulard, Fillaux, et al., 1986 | Crystal phase 1 phase; Uncertainty assigned by TRC = 1. K; phases identified by Raman spectrum; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 646. | K | N/A | Majer and Svoboda, 1985 | |
Tc | 646.3 | K | N/A | Kobe and Mathews, 1970 | Uncertainty assigned by TRC = 0.5 K; TRC |
Tc | 645.65 | K | N/A | Ambrose and Grant, 1957 | Uncertainty assigned by TRC = 0.5 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Pc | 45.99 | atm | N/A | Kobe and Mathews, 1970 | Uncertainty assigned by TRC = 0.5000 atm; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ρc | 3.07 | mol/l | N/A | Kobe and Mathews, 1970 | Uncertainty assigned by TRC = 0.21 mol/l; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 10.7 ± 0.1 | kcal/mol | AVG | N/A | Average of 9 values; Individual data points |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
8.965 | 418.5 | N/A | Majer and Svoboda, 1985 | |
10.4 ± 0.02 | 320. | EB | Chirico, Knipmeyer, et al., 1999 | Based on data from 328. to 459. K.; AC |
9.82 ± 0.02 | 360. | EB | Chirico, Knipmeyer, et al., 1999 | Based on data from 328. to 459. K.; AC |
9.27 ± 0.02 | 400. | EB | Chirico, Knipmeyer, et al., 1999 | Based on data from 328. to 459. K.; AC |
8.65 ± 0.05 | 440. | EB | Chirico, Knipmeyer, et al., 1999 | Based on data from 328. to 459. K.; AC |
9.89 | 363. | A | Stephenson and Malanowski, 1987 | Based on data from 348. to 460. K.; AC |
10.1 | 347. | A | Stephenson and Malanowski, 1987 | Based on data from 348. to 347. K.; AC |
9.56 | 396. | A | Stephenson and Malanowski, 1987 | Based on data from 381. to 460. K.; AC |
9.06 | 467. | A | Stephenson and Malanowski, 1987 | Based on data from 452. to 573. K.; AC |
8.89 | 579. | A | Stephenson and Malanowski, 1987 | Based on data from 564. to 646. K.; AC |
9.89 | 363. | EB,IP | Stephenson and Malanowski, 1987 | Based on data from 348. to 459. K. See also Osborn and Douslin, 1968.; AC |
10.5 ± 0.02 | 313. | C | Majer, Svoboda, et al., 1984 | AC |
10.3 ± 0.02 | 328. | C | Majer, Svoboda, et al., 1984 | AC |
10.1 ± 0.02 | 343. | C | Majer, Svoboda, et al., 1984 | AC |
9.87 | 365. | MG | Herington and Martin, 1953 | Based on data from 350. to 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. to 434. |
---|---|
A (kcal/mol) | 15.3 |
α | 0.5241 |
β | 0.1879 |
Tc (K) | 646. |
Reference | Majer 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 to 459.07 | 4.1641 | 1482.84 | -62.407 | Osborn and Douslin, 1968 | |
350.06 to 418.61 | 4.16667 | 1484.484 | -62.229 | Herington and Martin, 1953, 2 | Coefficents calculated by NIST from author's data. |
Enthalpy of sublimation
ΔsubH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
15.0 | 226. | A | Stephenson and Malanowski, 1987 | Based on data from 213. to 239. K.; AC |
Temperature of phase transition
Ttrs (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|
255.010 | crystaline, II | crystaline, I | Steele, Chirico, et al., 1986 | DH |
276.818 | crystaline, I | liquid | Steele, Chirico, et al., 1986 | DH |
Enthalpy of phase transition
ΔHtrs (kcal/mol) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
0.00 | 255.00 | crystaline, II | crystaline, I | Messerly, Todd, et al., 1988 | DH |
3.007238 | 276.818 | crystaline, I | liquid | Messerly, Todd, et al., 1988 | DH |
0.000020 | 255.010 | crystaline, II | crystaline, I | Messerly, Todd, et al., 1987 | DH |
3.0060 | 276.817 | crystaline, I | liquid | Messerly, Todd, et al., 1987 | DH |
Entropy of phase transition
ΔStrs (cal/mol*K) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
10.86 | 276.818 | crystaline, I | liquid | Messerly, Todd, et al., 1988 | DH |
10.86 | 276.817 | crystaline, I | liquid | Messerly, Todd, et al., 1987 | DH |
References
Go To: Top, Condensed phase thermochemistry data, Phase change data, 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]
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]
Notes
Go To: Top, Condensed phase thermochemistry data, Phase change data, References
- Symbols used in this document:
Cp,liquid Constant pressure heat capacity of liquid Pc Critical pressure 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 ΔHtrs Enthalpy of phase transition ΔStrs Entropy of phase transition ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions ΔsubH Enthalpy of sublimation ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions ρc Critical density - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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