Naphthalene, 1,8-dimethyl-
- Formula: C12H12
- Molecular weight: 156.2237
- IUPAC Standard InChIKey: XAABPYINPXYOLM-UHFFFAOYSA-N
- CAS Registry Number: 569-41-5
- 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: 1,8-Dimethylnaphthalene
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas Chromatography, 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
DRB - Donald R. Burgess, Jr.
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | 26.00 ± 0.72 | kcal/mol | Ccb | Mansson, 1974 | Author was aware that data differs from previously reported values; ALS |
ΔfH°gas | 25.96 | kcal/mol | N/A | Good, 1973 | Value computed using ΔfHsolid° value of 25.9±1.2 kj/mol from Good, 1973 and ΔsubH° value of 82.7 kj/mol from Mansson, 1974.; DRB |
Constant pressure heat capacity of gas
Cp,gas (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
9.70 | 50. | Thermodynamics Research Center, 1997 | p=1 bar.; GT |
16.7 | 100. | ||
23.6 | 150. | ||
30.74 | 200. | ||
41.54 | 273.15 | ||
45.22 | 298.15 | ||
45.48 | 300. | ||
59.25 | 400. | ||
70.79 | 500. | ||
80.19 | 600. | ||
87.81 | 700. | ||
94.14 | 800. | ||
99.45 | 900. | ||
103.9 | 1000. | ||
108. | 1100. | ||
111. | 1200. | ||
114. | 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 | 6.24 ± 0.72 | kcal/mol | Ccb | Mansson, 1974 | crystal phase; Author was aware that data differs from previously reported values; ALS |
ΔfH°solid | 6.19 ± 0.29 | kcal/mol | Ccb | Good, 1973 | crystal phase; ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°solid | -1544.7 ± 0.62 | kcal/mol | Ccb | Mansson, 1974 | crystal phase; Author was aware that data differs from previously reported values; Corresponding ΔfHºsolid = 6.24 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°solid | -1544.70 ± 0.25 | kcal/mol | Ccb | Good, 1973 | crystal phase; Corresponding ΔfHºsolid = 6.20 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°solid,1 bar | 53.709 | 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 |
---|---|---|---|
58.031 | 298.15 | Finke, Messerly, et al., 1977 | T = 10 to 440 K.; DH |
57.79 | 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
DRB - Donald R. Burgess, Jr.
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tfus | 335. | K | N/A | Kotula and Rabczuk, 1985 | Uncertainty assigned by TRC = 2. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 336.32 | K | N/A | Finke, Messerly, et al., 1977, 2 | Uncertainty assigned by TRC = 0.02 K; TRC |
Ttriple | 336.32 | K | N/A | Osborn and Douslin, 1975 | Uncertainty assigned by TRC = 0.02 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 19.8 ± 0.07 | kcal/mol | C | Månsson, Fredga, et al., 1974 | See also Pedley and Rylance, 1977.; AC |
ΔsubH° | 19.8 ± 0.07 | kcal/mol | C | Mansson, 1974 | crystal phase; Author was aware that data differs from previously reported values; ALS |
ΔsubH° | 19.8 | kcal/mol | N/A | Mansson, 1974 | DRB |
Reduced pressure boiling point
Tboil (K) | Pressure (atm) | Reference | Comment |
---|---|---|---|
413.2 | 0.024 | Weast and Grasselli, 1989 | BS |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
15.0 | 353. | A | Stephenson and Malanowski, 1987 | Based on data from 338. to 413. K. See also Osborn and Douslin, 1975, 2 and Boublik, Fried, et al., 1984.; AC |
15.5 | 336. | IP | Finke, Messerly, et al., 1977 | Based on data from 338. to 413. K.; AC |
14.9 | 360. | IP | Finke, Messerly, et al., 1977 | Based on data from 338. to 413. K.; AC |
14.5 | 380. | IP | Finke, Messerly, et al., 1977 | Based on data from 338. to 413. K.; AC |
14.3 | 400. | IP | Finke, Messerly, et al., 1977 | Based on data from 338. to 413. 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 |
---|---|---|---|---|---|
338. to 413. | 4.46840 | 2151.342 | -67.192 | Osborn and Douslin, 1975, 2 | Coefficents calculated by NIST from author's data. |
Enthalpy of sublimation
ΔsubH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
18.6 | 332. | A | Stephenson and Malanowski, 1987 | Based on data from 328. to 336. K.; AC |
19.0 | 336. | B | Osborn and Douslin, 1975, 2 | See also Colomina, Jimenez, et al., 1979.; AC |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
0.01120 | 336.33 | N/A | Finke, Messerly, et al., 1977 | DH |
4.429 | 338.2 | DSC | Cheon and Kim, 2007 | AC |
3.769 | 336.3 | N/A | Acree, 1991 | AC |
Entropy of fusion
ΔfusS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
11.20 | 336.33 | Finke, Messerly, et al., 1977 | DH |
Gas Chromatography
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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
Kovats' RI, non-polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Capillary | Squalane | 120. | 1440.8 | Gerasimenko and Nabivach, 1997 | Column length: 50. m |
Capillary | OV-101 | 140. | 1456.8 | Gerasimenko, Kirilenko, et al., 1981 | N2; Column length: 50. m; Column diameter: 0.3 mm |
Capillary | OV-101 | 160. | 1472.4 | Gerasimenko, Kirilenko, et al., 1981 | N2; Column length: 50. m; Column diameter: 0.3 mm |
Capillary | OV-1 | 130. | 1449. | Engewald, Wennrich, et al., 1979 | Column length: 50. m; Column diameter: 0.23 mm |
Packed | SE-30 | 150. | 1471. | Shlyakhov, Anvaer, et al., 1975 |
Van Den Dool and Kratz RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-5 | 1472.7 | Song, Lai, et al., 2003 | 30. m/0.25 mm/0.25 μm, He, 4. K/min; Tstart: 40. C; Tend: 310. C |
Capillary | DB-5 | 1472.1 | Song, Lai, et al., 2003 | 30. m/0.25 mm/0.25 μm, He, 40. C @ 5. min, 4. K/min; Tend: 310. C |
Capillary | DB-5 | 1459.7 | Song, Lai, et al., 2003 | 30. m/0.25 mm/0.25 μm, He, 2. K/min; Tstart: 40. C; Tend: 310. C |
Capillary | DB-5 | 1472.7 | Song, Lai, et al., 2003 | 30. m/0.25 mm/0.25 μm, He, 4. K/min; Tstart: 40. C; Tend: 310. C |
Capillary | DB-5 | 1480.0 | Song, Lai, et al., 2003 | 30. m/0.25 mm/0.25 μm, He, 6. K/min; Tstart: 40. C; Tend: 310. C |
Capillary | DB-5 | 1459.7 | Lai and Song, 1995 | 30. m/0.25 mm/0.25 μm, He, 2. K/min; Tstart: 40. C; Tend: 310. C |
Capillary | DB-5 | 1472.7 | Lai and Song, 1995 | 30. m/0.25 mm/0.25 μm, He, 4. K/min; Tstart: 40. C; Tend: 310. C |
Capillary | DB-5 | 1480. | Lai and Song, 1995 | 30. m/0.25 mm/0.25 μm, He, 6. K/min; Tstart: 40. C; Tend: 310. C |
Capillary | DB-5 | 1472.7 | Lai and Song, 1995 | 30. m/0.25 mm/0.25 μm, He, 4. K/min; Tstart: 40. C; Tend: 310. C |
Capillary | DB-5 | 1472.1 | Lai and Song, 1995 | 30. m/0.25 mm/0.25 μm, He, 40. C @ 5. min, 4. K/min; Tend: 310. C |
Capillary | SE-52 | 1450. | Beernaert, 1979 | He, 50. C @ 5. min, 6. K/min; Column length: 33.3 m; Column diameter: 0.50 mm; Tend: 320. C |
Van Den Dool and Kratz RI, polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Supelcowax-10 | 1989. | Riu-Aumatell, Lopez-Tamames, et al., 2005 | 30. m/0.25 mm/0.25 μm, He, 60. C @ 5. min, 3. K/min, 240. C @ 10. min |
Normal alkane RI, non-polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Capillary | OV-101 | 120. | 1457. | Nabivach and Gerasimenko, 1996 | |
Capillary | Polidimethyl siloxane | 130. | 1448. | Nabivach and Gerasimenko, 1996 | |
Capillary | Polidimethyl siloxane | 130. | 1449. | Nabivach and Gerasimenko, 1996 | |
Capillary | Polidimethyl siloxane | 130. | 1457. | Nabivach and Gerasimenko, 1996 |
Normal alkane RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | OV-1 | 1449. | Dimov, Osman, et al., 1994 | Program: not specified |
Lee's RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | SE-52 | 249.39 | Wang, Peng, et al., 1997 | 4. K/min; Column length: 30. m; Column diameter: 0.30 mm; Tstart: 40. C; Tend: 250. C |
Capillary | SE-52 | 252. | Vassilaros, Kong, et al., 1982 | 20. m/0.30 mm/0.25 μm, H2, 40. C @ 2. min, 4. K/min; Tend: 265. C |
Capillary | SE-52 | 249.52 | Lee, Vassilaros, et al., 1979 | 12. m/0.3 mm/0.34 μm, He, 2. K/min; Tstart: 50. C; Tend: 250. C |
Lee's RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-5 | 250.7 | Fuentes, Font, et al., 2007 | Column length: 60. m; Program: not specified |
Capillary | SE-52 | 249.52 | Wang, Peng, et al., 1997 | Column length: 30. m; Column diameter: 0.30 mm; Program: not specified |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas Chromatography, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Mansson, 1974
Mansson, M.,
A calorimetric study of peri strain in 1,8-Dimethylnaphthalene and 1,4,5,8-Tetramethylnaphthalene,
Acta Chem. Scand., Ser. B, 1974, 28, 677-680. [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]
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]
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]
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]
Månsson, Fredga, et al., 1974
Månsson, Margret; Fredga, Arne; Ställberg, Gunnel; Thorin, Hans,
A Calorimetric Study of peri Strain in 1,8-Dimethylnaphthalene and 1,4,5,8-Tetramethylnaphthalene.,
Acta Chem. Scand., 1974, 28b, 677-680, https://doi.org/10.3891/acta.chem.scand.28b-0677
. [all data]
Pedley and Rylance, 1977
Pedley, J.B.; Rylance, J.,
, Computer Analysed Thermochemical Data: Organic and Organometallic Compounds, University of Sussex, Brighton, 1977. [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]
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]
Colomina, Jimenez, et al., 1979
Colomina, M.; Jimenez, P.; Roux, M.V.; Turrion, C.,
An. Quim., 1979, 75, 620. [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]
Gerasimenko and Nabivach, 1997
Gerasimenko, V.A.; Nabivach, V.M.,
Sorption-structure correlations in the series of alkyl derivatives of naphthalene,
J. Anal. Chem. USSR (Engl. Transl.), 1997, 52, 1, 21-27. [all data]
Gerasimenko, Kirilenko, et al., 1981
Gerasimenko, V.A.; Kirilenko, A.V.; Nabivach, V.M.,
Capillary gas chromatography of aromatic compounds found in coal tar fractions,
J. Chromatogr., 1981, 208, 1, 9-16, https://doi.org/10.1016/S0021-9673(00)87953-4
. [all data]
Engewald, Wennrich, et al., 1979
Engewald, W.; Wennrich, L.; Ritter, E.,
Molekülstruktur und Retentionsverhalten. XII. Zur Retention von Alkylnaphthalinen Bei der Gasverteilungs- und Gas-Adsorptions-Chromatographie,
J. Chromatogr., 1979, 174, 2, 315-323, https://doi.org/10.1016/S0021-9673(00)86005-7
. [all data]
Shlyakhov, Anvaer, et al., 1975
Shlyakhov, A.F.; Anvaer, B.I.; Zolotareva, O.V.; Romina, N.N.; Novikova, N.V.; Koreshkova, R.I.,
On the possibility of group indentification of hydrocarbons by gas chromatography from temperature coefficients of retention indices,
Zh. Anal. Khim., 1975, 30, 788-792. [all data]
Song, Lai, et al., 2003
Song, C.; Lai, W.-C.; Madhusudan Reddy, K.; Wei, B.,
Chapter 7. Temperature-programmed retention indices for GC and GC-MS of hydrocarbon fuels and simulated distillation GC of heavy oils
in Analytical advances for hydrocarbon research, Hsu,C.S., ed(s)., Kluwer Academic/Plenum Publishers, New York, 2003, 147-193. [all data]
Lai and Song, 1995
Lai, W.-C.; Song, C.,
Temperature-programmed retention indices for g.c. and g.c.-m.s. analysis of coal- and petroleum-derived liquid fuels,
Fuel, 1995, 74, 10, 1436-1451, https://doi.org/10.1016/0016-2361(95)00108-H
. [all data]
Beernaert, 1979
Beernaert, H.,
Gas Chromatographic Analysis of Polyclylic Aromatic Hydrocarbons,
J. Chromatogr., 1979, 173, 1, 109-118, https://doi.org/10.1016/S0021-9673(01)80450-7
. [all data]
Riu-Aumatell, Lopez-Tamames, et al., 2005
Riu-Aumatell, M.; Lopez-Tamames, E.; Buxaderas, S.,
Assessment of the Volatile Composition of Juices of Apricot, Peach, and Pear According to Two Pectolytic Treatments,
J. Agric. Food Chem., 2005, 53, 20, 7837-7843, https://doi.org/10.1021/jf051397z
. [all data]
Nabivach and Gerasimenko, 1996
Nabivach, V.M.; Gerasimenko, V.A.,
Gas chromatographic retention characteristics of bicyclic aromatic hydrocarbons,
Coke and Chemistry (Rus), 1996, 6, 27-31. [all data]
Dimov, Osman, et al., 1994
Dimov, N.; Osman, A.; Mekenyan, Ov.; Papazova, D.,
Selection of moelcular descriptors used in quantitative structure-gas chromatographic retention relationships. I. Application to alkylbenzenes and naphthalenes,
Anal. Chim. Acta., 1994, 298, 3, 303-317, https://doi.org/10.1016/0003-2670(94)00280-0
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Wang, Peng, et al., 1997
Wang, Y.; Peng, P.; Cui, S.; Zhang, Y.,
Identification of PAH in the Suzhou River bed sediments by GC/MS and PAH retention index system,
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Vassilaros, Kong, et al., 1982
Vassilaros, D.L.; Kong, R.C.; Later, D.W.; Lee, M.L.,
Linear retention index system for polycyclic aromatic compounds. Critical evaluation and additional indices,
J. Chromatogr., 1982, 252, 1-20, https://doi.org/10.1016/S0021-9673(01)88394-1
. [all data]
Lee, Vassilaros, et al., 1979
Lee, M.L.; Vassilaros, D.L.; White, C.M.; Novotny, M.,
Retention Indices for Programmed-Temperature Capillary-Column Gas Chromatography of Polycyclic Aromatic Hydrocarbons,
Anal. Chem., 1979, 51, 6, 768-773, https://doi.org/10.1021/ac50042a043
. [all data]
Fuentes, Font, et al., 2007
Fuentes, M.J.; Font, R.; Gomez-Rico, M.F.; Martin-Gullon, I.,
Pyrolysis and combustion of waste lubricant oil from diesel cars: Decomposition and pollutants,
J. Anal. Appl. Pyrolysis, 2007, 79, 1-2, 215-226, https://doi.org/10.1016/j.jaap.2006.12.004
. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas Chromatography, References
- Symbols used in this document:
Cp,gas Constant pressure heat capacity of gas Cp,solid Constant pressure heat capacity of solid 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°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 - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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