Naphthalene, decahydro-, trans-
- Formula: C10H18
- Molecular weight: 138.2499
- IUPAC Standard InChIKey: NNBZCPXTIHJBJL-MGCOHNPYSA-N
- CAS Registry Number: 493-02-7
- 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. - Stereoisomers:
- Other names: trans-Bicyclo[4.4.0]Decane; trans-Decahydronaphthalene; trans-Decalin; trans-Perhydronaphthalene; Decahydronaphthalene, trans-; Decahydronaphthalene, (E)-; (E)-Decahydronaphthalene; t-Decalin; Bicyclo[4.4.0]decane, isomer # 1; trans-Decaline
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Condensed phase thermochemistry data
Go To: Top, 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 | -55.14 ± 0.22 | kcal/mol | Ccb | Speros and Rossini, 1960 | ALS |
ΔfH°liquid | -54.65 ± 0.32 | kcal/mol | Ccb | Davies and Gilbert, 1941 | Reanalyzed by Cox and Pilcher, 1970, Original value = -54.87 kcal/mol; ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -1500.23 ± 0.22 | kcal/mol | Ccb | Speros and Rossini, 1960 | Corresponding ΔfHºliquid = -55.12 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°liquid | -1500.70 ± 0.30 | kcal/mol | Ccb | Davies and Gilbert, 1941 | Reanalyzed by Cox and Pilcher, 1970, Original value = -1500.3 ± 0.1 kcal/mol; Corresponding ΔfHºliquid = -54.65 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°liquid | -1497.1 ± 0.5 | kcal/mol | Ccb | Huckel, Kamenz, et al., 1937 | Corresponding ΔfHºliquid = -58.2 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°liquid | -1495.2 | kcal/mol | Ccb | Huckel and Mentzel, 1926 | Corresponding ΔfHºliquid = -60.1 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°liquid | -1498.1 ± 1.1 | kcal/mol | Ccb | Roth and Lasse, 1925 | Corresponding ΔfHºliquid = -57.21 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°liquid | 63.320 | cal/mol*K | N/A | McCullough, Finke, et al., 1957 | DH |
Constant pressure heat capacity of liquid
Cp,liquid (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
54.773 | 298.15 | Ohnishi, Fujihara, et al., 1989 | DH |
54.773 | 298.15 | Shiohama, Ogawa, et al., 1988 | DH |
54.773 | 298.15 | Shiohama, Ogawa, et al., 1988, 2 | DH |
59.89 | 313. | Gudinowicz, Campbell, et al., 1963 | T = 313 to 423 K.; DH |
54.610 | 298.15 | McCullough, Finke, et al., 1957 | T = 10 to 350 K.; DH |
54.221 | 298. | Seyer, 1953 | T = 293 to 413 K.; DH |
52.036 | 298.15 | Parks and Hatton, 1949 | T = 80 to 298.15 K.; DH |
References
Go To: Top, Condensed phase thermochemistry data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Speros and Rossini, 1960
Speros, D.M.; Rossini, F.D.,
Heats of combustion and formation of naphthalene, the two methylnaphthalenes, cis and trans decahydronaphthalene and related compounds,
J. Phys. Chem., 1960, 64, 1723-1727. [all data]
Davies and Gilbert, 1941
Davies, G.F.; Gilbert, E.C.,
The heat of combustion of cis- and trans-decahydronaphthalene,
J. Am. Chem. Soc., 1941, 63, 1585-1586. [all data]
Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G.,
Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]
Huckel, Kamenz, et al., 1937
Huckel, W.; Kamenz, E.; Gross, A.; Tappe, W.,
Zur kenntnis der waldenschen umkehrung,
Ann. Chim., 1937, 533, 1-45. [all data]
Huckel and Mentzel, 1926
Huckel, W.; Mentzel, R.,
Zur Stereochemie bicyclischer Ringsteme II. Die Stereoisomerie des Dekahydronaphtalins und seiner Derivate II. Stereoisomere β-substituierte Dekaline,
Ann., 1926, 451, 109-132. [all data]
Roth and Lasse, 1925
Roth, W.A.; Lasse, R.,
Verbrennungswarme der Dekahydro-naphthaline und der Dekalone,
Ann., 1925, 441, 48-53. [all data]
McCullough, Finke, et al., 1957
McCullough, J.P.; Finke, H.L.; Messerly, J.F.; Kincheloe, T.C.; Waddington, G.,
The low temperature thermodynamic properties of naphthalene, 1-methylnaphthalene, 2-methylnaphthalene, 1,2,3,4-tetrahydronaphthalene, trans-decahydronaphthalene and cis-decahydronaphthalene,
J. Phys. Chem., 1957, 61, 1105-1116. [all data]
Ohnishi, Fujihara, et al., 1989
Ohnishi, K.; Fujihara, I.; Murakami, S.,
Thermodynamic properties of decalins mixed with hexane isomers at 298.15K. 1. Excess enthalpies and excess isobaric heat capacities,
Fluid Phase Equilib., 1989, 46, 59-72. [all data]
Shiohama, Ogawa, et al., 1988
Shiohama, Y.; Ogawa, H.; Murakami, S.; Fujihara, I.,
Excess molar isobaric heat capacities and isentropic compressibilities of (cis- or trans-decalin + benzene or toluene or iso-octane or n-heptane) at 298.15 K,
J. Chem. Thermodynam., 1988, 20, 1183-1189. [all data]
Shiohama, Ogawa, et al., 1988, 2
Shiohama, Y.; Ogawa, H.; Murakami, S.; Fujihara, I.,
Excess thermodynamic properties of (cis-decalin or trans-decalin + cyclohexane or methylcyclohexane or cyclooctane) at 298.15 K,
J. Chem. Thermodynam., 1988, 20, 1307-1314. [all data]
Gudinowicz, Campbell, et al., 1963
Gudinowicz, B.J.; Campbell, R.H.; Adams, J.S.,
Specific heat measurements of complex saturated hydrocarbons,
J. Chem. Eng. Data, 1963, 8, 201-214. [all data]
Seyer, 1953
Seyer, W.F.,
The heat capacity of cis- and trans-decahydronaphthalene and the possible existence of a lambda-region for the cis form at 50.1-50.5,
J. Am. Chem. Soc., 1953, 75, 616-621. [all data]
Parks and Hatton, 1949
Parks, G.S.; Hatton, J.A.,
Thermal data on organic compounds. XXIV. The heat capacities, entropies and free energies of cis- and trans-decahydronaphthalene,
J. Am. Chem. Soc., 1949, 71, 2773-2775. [all data]
Notes
Go To: Top, Condensed phase thermochemistry data, References
- Symbols used in this document:
Cp,liquid Constant pressure heat capacity of liquid S°liquid Entropy of liquid at standard conditions ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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