Naphthalene, 2,6-dimethyl-
- Formula: C12H12
- Molecular weight: 156.2237
- IUPAC Standard InChIKey: YGYNBBAUIYTWBF-UHFFFAOYSA-N
- CAS Registry Number: 581-42-0
- 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-Dimethylnaphthalene
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics 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 by: Glushko Thermocenter, Russian Academy of Sciences, Moscow
Constant pressure heat capacity of gas
Cp,gas (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
11.9 | 50. | Thermodynamics Research Center, 1997 | p=1 bar. |
18.3 | 100. | ||
23.7 | 150. | ||
29.76 | 200. | ||
39.70 | 273.15 | ||
43.21 | 298.15 | ||
43.48 | 300. | ||
57.10 | 400. | ||
68.86 | 500. | ||
78.51 | 600. | ||
86.42 | 700. | ||
92.97 | 800. | ||
98.45 | 900. | ||
103.1 | 1000. | ||
107. | 1100. | ||
110. | 1200. | ||
113. | 1300. | ||
116. | 1400. | ||
118. | 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 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°solid | -1.37 ± 0.40 | kcal/mol | Ccb | Good, 1973 | crystal phase; ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°solid | -1537.14 ± 0.38 | kcal/mol | Ccb | Good, 1973 | crystal phase; Corresponding ΔfHºsolid = -1.36 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°solid,1 bar | 54.460 | cal/mol*K | N/A | Finke, Messerly, et al., 1977 | DH |
Constant pressure heat capacity of solid
Cp,solid (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
48.650 | 298.15 | Finke, Messerly, et al., 1977 | T = 10 to 440 K.; DH |
48.40 | 298.15 | Good, 1973 | 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
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 536. ± 6. | K | AVG | N/A | Average of 7 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 387.4 | K | N/A | Kotula and Rabczuk, 1985 | Uncertainty assigned by TRC = 2. K; TRC |
Tfus | 383.27 | K | N/A | Szafranski, 1984 | Uncertainty assigned by TRC = 0.1 K; TRC |
Tfus | 383.9 | K | N/A | Smith, 1980 | Uncertainty assigned by TRC = 0.2 K; TRC |
Tfus | 384.15 | K | N/A | Luther and Riechel, 1950 | Uncertainty assigned by TRC = 0.5 K; TRC |
Tfus | 336. | K | N/A | Linstead, Millidge, et al., 1937 | Uncertainty assigned by TRC = 4. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 383.31 | K | N/A | Finke, Messerly, et al., 1977, 2 | Uncertainty assigned by TRC = 0.02 K; TRC |
Ttriple | 383.31 | K | N/A | Osborn and Douslin, 1975 | Uncertainty assigned by TRC = 0.03 K; TRC |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
13.7 | 399. | A | Stephenson and Malanowski, 1987 | Based on data from 384. to 418. K. See also Osborn and Douslin, 1975, 2 and Boublik, Fried, et al., 1984.; AC |
13.7 | 383. | IP | Finke, Messerly, et al., 1977 | Based on data from 384. to 418. K.; AC |
13.5 | 400. | IP | Finke, Messerly, et al., 1977 | Based on data from 384. to 418. K.; AC |
13.3 | 420. | IP | Finke, Messerly, et al., 1977 | Based on data from 384. to 418. K.; 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 |
---|---|---|---|---|---|
384. to 418. | 3.14260 | 1302.791 | -135.652 | Osborn and Douslin, 1975, 2 | Coefficents calculated by NIST from author's data. |
Enthalpy of sublimation
ΔsubH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
20.2 ± 0.45 | 366. | N/A | Finke, Messerly, et al., 1977 | Based on data from 350. to 383. K. See also Osborn and Douslin, 1975, 2 and Stephenson and Malanowski, 1987.; AC |
19.7 | 383. | B | Osborn and Douslin, 1975, 2 | AC |
20.07 ± 0.09 | 379.2 | V | Aihara, 1959 | crystal phase; ALS |
20.1 | 291. | V | Aihara, 1959, 2 | Based on data from 279. to 304. K. See also Stephenson and Malanowski, 1987.; AC |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
5.98870 | 383.32 | N/A | Finke, Messerly, et al., 1977 | DH |
6.05 | 385.2 | DSC | Cheon and Kim, 2007 | AC |
5.989 | 383.3 | N/A | Acree, 1991 | AC |
Entropy of fusion
ΔfusS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
15.62 | 383.32 | Finke, Messerly, et al., 1977 | 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: John E. Bartmess
Electron affinity determinations
EA (eV) | Method | Reference | Comment |
---|---|---|---|
<0.160 ± 0.074 | ECD | Wojnarovits and Foldiak, 1981 | EA is an upper limit: Chen and Wentworth, 1989. G3MP2B3 calculations indicate an EA of ca. -0.1 eV, anion unbound. |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Thermodynamics Research Center, 1997
Thermodynamics Research Center,
Selected Values of Properties of Chemical Compounds., Thermodynamics Research Center, Texas A&M University, College Station, Texas, 1997. [all data]
Good, 1973
Good, W.D.,
The enthalpies of combustion and formation of 1,8-dimethylnaphthalene, 2,3-dimethylnaphthalene, 2,6-dimethylnaphthalene, and 2,7-dimethylnaphthalene,
J. Chem. Thermodyn., 1973, 5, 715-720. [all data]
Finke, Messerly, et al., 1977
Finke, H.L.; Messerly, J.F.; Lee, S.H.; Osborn, A.G.; Douslin, D.R.,
Comprehensive thermodynamic studies of seven aromatic hydrocarbons,
J. Chem. Thermodyn., 1977, 9, 937-956. [all data]
Kotula and Rabczuk, 1985
Kotula, I.; Rabczuk, A.,
DTA Investigation of the Solid-Liquid Equilibrium for Mehtyl Derivatives of Naphthalene with Some Nitroaromatics,
J. Therm. Anal., 1985, 30, 195. [all data]
Szafranski, 1984
Szafranski, A.M.,
Solid-Liquid Equilibrium,
Int. DATA Ser., Sel. Data Mixtures, Ser. A, 1984, No. 1, 40-50. [all data]
Smith, 1980
Smith, G.W.,
Phase behavior of some condensed polycyclic aromatics,
Mol. Cryst. Liq. Cryst., 1980, 64, 15. [all data]
Luther and Riechel, 1950
Luther, H.; Riechel, C.,
The Raman Spectra of Polymethylnphthalenes,
Z. Phys. Chem. (Leipzig), 1950, 195, 103. [all data]
Linstead, Millidge, et al., 1937
Linstead; Millidge; Walpole,
J. Chem. Soc., 1937, 1937, 1140. [all data]
Finke, Messerly, et al., 1977, 2
Finke, H.L.; Messerly, J.F.; Lee, S.H.; Osborn, A.G.; Douslin, D.R.,
Comprehensive thermodynamic studies of seven aromatic hydrocarbons,
J. Chem. Thermodyn., 1977, 9, 937. [all data]
Osborn and Douslin, 1975
Osborn, A.G.; Douslin, D.R.,
Vapor Pressure and Derived Enthalpies of Vaporization for Some Condensed Ring Hydrocarbons,
J. Chem. Eng. Data, 1975, 20, 229-31. [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, 1975, 2
Osborn, Ann G.; Douslin, Donald R.,
Vapor pressures and derived enthalpies of vaporization for some condensed-ring hydrocarbons,
J. Chem. Eng. Data, 1975, 20, 3, 229-231, https://doi.org/10.1021/je60066a022
. [all data]
Boublik, Fried, et al., 1984
Boublik, T.; Fried, V.; Hala, E.,
The Vapour Pressures of Pure Substances: Selected Values of the Temperature Dependence of the Vapour Pressures of Some Pure Substances in the Normal and Low Pressure Region, 2nd ed., Elsevier, New York, 1984, 972. [all data]
Aihara, 1959
Aihara, A.,
Estimation of the energy of hydrogen bonds formed in crystals. I. Sublimation pressures of some organic molecular crystals and the additivity of lattice energy,
Bull. Chem. Soc. Jpn., 1959, 32, 1242. [all data]
Aihara, 1959, 2
Aihara, Ariyuki,
Estimation of the Energy of Hydrogen Bonds Formed in Crystals. I. Sublimation Pressures of Some Organic Molecular Crystals and the Additivity of Lattice Energy,
Bull. Chem. Soc. Jpn., 1959, 32, 11, 1242-1248, https://doi.org/10.1246/bcsj.32.1242
. [all data]
Cheon and Kim, 2007
Cheon, Yang-Ho; Kim, Kwang-Joo,
Solid-Liquid Equilibria of Binary Mixtures of Dimethylnaphthalene Isomers,
J. Chem. Eng. Data, 2007, 52, 4, 1390-1393, https://doi.org/10.1021/je700088n
. [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]
Wojnarovits and Foldiak, 1981
Wojnarovits, L.; Foldiak, G.,
Electron capture detection of aromatic hydrocarbons,
J. Chromatogr. Sci., 1981, 206, 511. [all data]
Chen and Wentworth, 1989
Chen, E.C.M.; Wentworth, W.E.,
Experimental Determination of Electron Affinities of Organic Molecules,
Mol. Cryst. Liq. Cryst., 1989, 171, 271. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, References
- Symbols used in this document:
Cp,gas Constant pressure heat capacity of gas Cp,solid Constant pressure heat capacity of solid EA Electron affinity S°solid,1 bar Entropy of solid at standard conditions (1 bar) Tboil Boiling point Tfus Fusion (melting) point Ttriple Triple point temperature ΔcH°solid Enthalpy of combustion of solid 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 ΔvapH Enthalpy of vaporization - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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