Pyridine, 2,5-dimethyl-
- Formula: C7H9N
- Molecular weight: 107.1531
- IUPAC Standard InChIKey: XWKFPIODWVPXLX-UHFFFAOYSA-N
- CAS Registry Number: 589-93-5
- Chemical structure:
This structure is also available as a 2d Mol file - Other names: 2,5-Lutidine; 2,5-Dimethylpyridine; 5-methyl-2-methylpyridine
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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 | 4.44 | kcal/mol | Ccb | Cox and Gundry, 1958 | see Cox, Challoner, et al., 1954; ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -970.23 | kcal/mol | Ccb | Cox and Gundry, 1958 | see Cox, Challoner, et al., 1954; ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°liquid | 59.467 | 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 |
---|---|---|---|
44.144 | 298.15 | Steele, Chirico, et al., 1986 | T = 10 to 450 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
DH - Eugene S. Domalski and Elizabeth D. Hearing
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 431.2 | K | N/A | Weast and Grasselli, 1989 | BS |
Tboil | 429.9 | K | N/A | Jankun-Pinska, 1964 | Uncertainty assigned by TRC = 0.3 K; TRC |
Tboil | 426.65 | K | N/A | Prostakov, Gaivoronskaya, et al., 1963 | Uncertainty assigned by TRC = 3. K; TRC |
Tboil | 429.15 | K | N/A | Farberov, Kut'in, et al., 1961 | Uncertainty assigned by TRC = 2. K; TRC |
Tboil | 426.25 | K | N/A | Kyte, Jeffery, et al., 1960 | Uncertainty assigned by TRC = 1.5 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 259.070 | K | N/A | Steele, Chirico, et al., 1986 | DH |
Tfus | 257.15 | K | N/A | Kyte, Jeffery, et al., 1960 | Uncertainty assigned by TRC = 0.5 K; TRC |
Tfus | 257.61 | K | N/A | Coulson, Cox, et al., 1959 | Uncertainty assigned by TRC = 0.03 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 259.07 | K | N/A | Chirico, Hossenlopp, et al., 1994 | Uncertainty assigned by TRC = 0.01 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 644.16 | K | N/A | Ambrose, Cox, et al., 1960 | Uncertainty assigned by TRC = 0.3 K; Visual, PRT, IPTS-48; TRC |
Tc | 644.15 | K | N/A | Cox, 1960 | Uncertainty assigned by TRC = 1. K; measured by R. Townsend to be pub. later; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 11.43 | kcal/mol | V | Cox, 1960 | ALS |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
10.6 | 340. | EB | Steele, Chirico, et al., 1995 | Based on data from 330. to 471. K.; AC |
10.0 | 380. | EB | Steele, Chirico, et al., 1995 | Based on data from 330. to 471. K.; AC |
9.42 | 420. | EB | Steele, Chirico, et al., 1995 | Based on data from 330. to 471. K.; AC |
8.72 | 460. | EB | Steele, Chirico, et al., 1995 | Based on data from 330. to 471. K.; AC |
10.2 | 373. | A,MG | Stephenson and Malanowski, 1987 | Based on data from 358. to 431. K. See also Herington and Martin, 1953 and Kkykj and Repas, 1973.; AC |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (atm)
T = temperature (K)
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Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
358.3 to 430.5 | 4.25365 | 1574.069 | -60.039 | Herington and Martin, 1953, 2 | Coefficents calculated by NIST from author's data. |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
3.499 | 259.1 | Chirico, Hossenlopp, et al., 1994, 2 | AC |
Temperature of phase transition
Ttrs (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|
182.200 | crystaline, II | crystaline, I | Steele, Chirico, et al., 1986 | 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.
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]
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]
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]
Jankun-Pinska, 1964
Jankun-Pinska, J.,
Liquid-liquid equilibrium in series of ternary systems formed by pyridine bases, benzene and water. II. ternary systems: 2,4-lutidine-benzene-water, 2,5-lutidine-benzene-water and 2,6-lutidine-b,
Bull. Acad. Pol. Sci., Ser. Sci. Chim., 1964, 12, 843. [all data]
Prostakov, Gaivoronskaya, et al., 1963
Prostakov, N.S.; Gaivoronskaya, L.A.; Mikheeva, N.N.; Filippov, N.P.,
Substituted Pyridines: 2,5-Dimethyl-4-alkylpyridines,
Zh. Obshch. Khim., 1963, 33, 2928. [all data]
Farberov, Kut'in, et al., 1961
Farberov, M.I.; Kut'in, A.M.; Ustavshchikov, V.F.,
The conditions of 2-methyl-5-vinylprydine synthesis,
Zh. Prikl. Khim. (Leningrad), 1961, 34, 632. [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]
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]
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]
Kkykj and Repas, 1973
Kkykj, J.; Repas, M.,
Petrochemia, 1973, 13, 179. [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]
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 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°liquid Enthalpy of formation of liquid at standard conditions ΔfusH Enthalpy of fusion 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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