Phenol, 2,6-dimethyl-
- Formula: C8H10O
- Molecular weight: 122.1644
- IUPAC Standard InChIKey: NXXYKOUNUYWIHA-UHFFFAOYSA-N
- CAS Registry Number: 576-26-1
- 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: 2,6-Xylenol; 2,6-Dimethylphenol; 1,2,6-Xylenol; 1,3-Dimethyl-2-hydroxybenzene; 1-Hydroxy-2,6-dimethylbenzene; 2,6-Dmp; NSC 2123
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics 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 as indicated in comments:
DRB - Donald R. Burgess, Jr.
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | -37.64 | kcal/mol | N/A | Lebedev, Vasil'ev, et al., 1996 | Value computed using ΔfHsolid° value of -233.1±2.9 kj/mol from Lebedev, Vasil'ev, et al., 1996 and ΔsubH° value of 75.6 kj/mol from Andon, Biddiscombe, et al., 1960.; DRB |
ΔfH°gas | -41.68 | kcal/mol | N/A | Lindberg, Jauhiainen, et al., 1972 | Value computed using ΔfHsolid° value of -250.0 kj/mol from Lindberg, Jauhiainen, et al., 1972 and ΔsubH° value of 75.6 kj/mol from Andon, Biddiscombe, et al., 1960.; DRB |
ΔfH°gas | -38.68 ± 0.13 | kcal/mol | Ccb | Andon, Biddiscombe, et al., 1960 | ALS |
Constant pressure heat capacity of gas
Cp,gas (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
10.29 | 50. | Kudchadker S.A., 1979 | GT |
15.99 | 100. | ||
21.78 | 150. | ||
27.070 | 200. | ||
34.673 | 273.15 | ||
37.278 | 298.15 | ||
37.471 | 300. | ||
47.457 | 400. | ||
56.102 | 500. | ||
63.231 | 600. | ||
69.099 | 700. | ||
73.984 | 800. | ||
78.102 | 900. | ||
81.604 | 1000. | ||
84.601 | 1100. | ||
87.175 | 1200. | ||
89.393 | 1300. | ||
91.315 | 1400. | ||
92.980 | 1500. |
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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°solid | -55.71 ± 0.69 | kcal/mol | Ccb | Lebedev, Vasil'ev, et al., 1996 | |
ΔfH°solid | -59.7 | kcal/mol | Ccb | Lindberg, Jauhiainen, et al., 1972 | |
ΔfH°solid | -56.75 ± 0.26 | kcal/mol | Ccb | Andon, Biddiscombe, et al., 1960 | |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°solid | -1038.3 ± 0.69 | kcal/mol | Ccb | Lebedev, Vasil'ev, et al., 1996 | Corresponding ΔfHºsolid = -55.69 kcal/mol (simple calculation by NIST; no Washburn corrections) |
ΔcH°solid | -1033.8 | kcal/mol | Ccb | Lindberg, Jauhiainen, et al., 1972 | Corresponding ΔfHºsolid = -60.2 kcal/mol (simple calculation by NIST; no Washburn corrections) |
ΔcH°solid | -1037.25 ± 0.24 | kcal/mol | Ccb | Andon, Biddiscombe, et al., 1960 | Corresponding ΔfHºsolid = -56.73 kcal/mol (simple calculation by NIST; no Washburn corrections) |
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 |
---|---|---|---|---|---|
Tboil | 474. ± 2. | K | AVG | N/A | Average of 7 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 320. ± 3. | K | AVG | N/A | Average of 13 out of 14 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 700.95 | K | N/A | Ambrose, 1963 | Uncertainty assigned by TRC = 0.2 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 18.00 | kcal/mol | N/A | Majer and Svoboda, 1985 | |
ΔvapH° | 18.1 | kcal/mol | N/A | Morawetz, 1971 | AC |
ΔvapH° | 17.9 | kcal/mol | N/A | Morawetz, Elvebredd, et al., 1968 | AC |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 18.1 | kcal/mol | N/A | Morawetz, 1971 | AC |
ΔsubH° | 17.9 | kcal/mol | N/A | Morawetz, Elvebredd, et al., 1968 | Author of Morawetz, Elvebredd, et al., 1968 refers to the determined value as the enthalpy of vaporization even though the compound is a solid; AC |
ΔsubH° | 18.07 ± 0.04 | kcal/mol | V | Andon, Biddiscombe, et al., 1960 | ALS |
ΔsubH° | 18.1 | kcal/mol | N/A | Andon, Biddiscombe, et al., 1960 | DRB |
ΔsubH° | 14.2 ± 0.2 | kcal/mol | V | Wolf and Weghofer, 1938 | ALS |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
11.6 | 432. | A,GS,EB | Stephenson and Malanowski, 1987 | Based on data from 417. to 476. K. See also Andon, Biddiscombe, et al., 1960, 2.; 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 |
---|---|---|---|---|---|
418.0 to 476.67 | 4.20374 | 1638.455 | -84.416 | Andon, Biddiscombe, et al., 1960 | Coefficents calculated by NIST from author's data. |
Enthalpy of sublimation
ΔsubH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
18.1 ± 0.041 | 277. to 313. | GS | Andon, Biddiscombe, et al., 1960, 2 | See also Cox and Pilcher, 1970.; AC |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
4.5165 | 318.9 | N/A | Poeti, Fanelli, et al., 1982 | DH |
4.500 | 318.6 | DSC | Jamróz, Palczewska-Tulinska, et al., 1998 | AC |
4.52 | 318.9 | N/A | Acree, 1991 | AC |
Entropy of fusion
ΔfusS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
14.16 | 318.9 | Poeti, Fanelli, et al., 1982 | DH |
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 compiled by: Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
View reactions leading to C8H10O+ (ion structure unspecified)
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
8.05 ± 0.02 | PE | Maier and Turner, 1973 | |
8.26 | PE | Kobayashi and Nagakura, 1974 | Vertical value |
8.34 | PE | Dewar, Ernstbrunner, et al., 1974 | Vertical value |
IR Spectrum
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Data compiled by: Coblentz Society, Inc.
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Lebedev, Vasil'ev, et al., 1996
Lebedev, B.V.; Vasil'ev, V.G.; Bykova, T.A.; Kiparisova, E.G.; Wunderliche, B.,
Thermodynamics of 2,6-dimethylphenol, of the reaction of its oxidative dehydropolycondensation, and of the resultant poly(2,6-dimethyl-p-phenylene oxide)at 0-600 K,
Vysokomol. Soedin., Ser. A, 1996, 38, 216-225. [all data]
Andon, Biddiscombe, et al., 1960
Andon, R.J.L.; Biddiscombe, D.P.; Cox, J.D.; Handley, R.; Harrop, D.; Herington, E.F.G.; Martin, J.F.,
Thermodynamic properties of organic oxygen compounds. Part I. Preparation and physical properties of pure phenol, cresols, and xylenols,
J. Chem. Soc., 1960, 5246-5254. [all data]
Lindberg, Jauhiainen, et al., 1972
Lindberg, J.J.; Jauhiainen, T.P.; Savolainen, A.,
Oxidative coupling of 2,6-disubstituted phenols and the heat of combustion of the resulting products,
Pap. Puu, 1972, 54, 91-93. [all data]
Kudchadker S.A., 1979
Kudchadker S.A.,
Property data available for coal chemicals,
Hydrocarbon Process., 1979, 58, 169-171. [all data]
Ambrose, 1963
Ambrose, D.,
Critical Temperatures of Some Phenols and Other Organic Compounds,
Trans. Faraday Soc., 1963, 59, 1988. [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]
Morawetz, 1971
Morawetz, E.,
Chem. Scr., 1971, 1, 103. [all data]
Morawetz, Elvebredd, et al., 1968
Morawetz, Ernst; Elvebredd, I.; Brunvoll, J.; Hagen, G.; Paasivirta, Jaakko,
A Non-Equilibrium Low Vapor Pressure Heat of Vaporization Calorimeter. Part I. Vapor Pressure Range 200-10^-3 mm Hg.,
Acta Chem. Scand., 1968, 22, 1509-1531, https://doi.org/10.3891/acta.chem.scand.22-1509
. [all data]
Wolf and Weghofer, 1938
Wolf, K.L.; Weghofer, H.,
Uber sublimationswarmen,
Z. Phys. Chem., 1938, 39, 194-208. [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]
Andon, Biddiscombe, et al., 1960, 2
Andon, R.J.L.; Biddiscombe, D.P.; Cox, J.D.; Handley, R.; Harrop, D.; Herington, E.F.G.; Martin, J.F.,
1009. Thermodynamic properties of organic oxygen compounds. Part I. Preparation and physical properties of pure phenol, cresols, and xylenols,
J. Chem. Soc., 1960, 5246, https://doi.org/10.1039/jr9600005246
. [all data]
Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G.,
Thermochemistry of Organic and Organometallic Compounds, Academic Press Inc., London, 1970, 643. [all data]
Poeti, Fanelli, et al., 1982
Poeti, G.; Fanelli, E.; Braghetti, M.,
A differential scanning calorimetric study of some phenol derivatives,
J. Therm. Anal., 1982, 24(2), 273-279. [all data]
Jamróz, Palczewska-Tulinska, et al., 1998
Jamróz, Malgorzata E.; Palczewska-Tulinska, Marcela; Wyrzykowska-Stankiewicz, Danuta; Szafranski, Andrzej M.; Polaczek, Jerzy; Dobrowolski, Jan Cz.; Jamróz, Michal H.; Mazurek, Aleksander P.,
The urea--phenol(s) systems,
Fluid Phase Equilibria, 1998, 152, 2, 307-326, https://doi.org/10.1016/S0378-3812(98)90206-0
. [all data]
Acree, 1991
Acree, William E.,
Thermodynamic properties of organic compounds: enthalpy of fusion and melting point temperature compilation,
Thermochimica Acta, 1991, 189, 1, 37-56, https://doi.org/10.1016/0040-6031(91)87098-H
. [all data]
Maier and Turner, 1973
Maier, J.P.; Turner, D.W.,
Steric inhibition of resonance studied by molecular photoelectron spectroscopy Part 3. Anilines, Phenols and Related Compounds,
J. Chem. Soc. Faraday Trans. 2, 1973, 69, 521. [all data]
Kobayashi and Nagakura, 1974
Kobayashi, T.; Nagakura, S.,
Photoelectron spectra of substituted benzenes,
Bull. Chem. Soc. Jpn., 1974, 47, 2563. [all data]
Dewar, Ernstbrunner, et al., 1974
Dewar, P.S.; Ernstbrunner, E.; Gilmore, J.R.; Godfrey, M.; Mellor, J.M.,
Conformational analysis of alkyl aryl ethers and alkyl aryl sulphides by photoelectron spectroscopy,
Tetrahedron, 1974, 30, 2455. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, References
- Symbols used in this document:
Cp,gas Constant pressure heat capacity of gas Tboil Boiling point Tc Critical temperature Tfus Fusion (melting) point ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°solid Enthalpy of formation of solid at standard conditions ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion ΔsubH Enthalpy of sublimation ΔsubH° Enthalpy of sublimation at standard conditions 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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