Naphthalene, decahydro-, trans-
- Formula: C10H18
- Molecular weight: 138.2499
- IUPAC Standard InChI: InChI=1S/C10H18/c1-2-6-10-8-4-3-7-9(10)5-1/h9-10H,1-8H2/t9-,10-
- 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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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Reaction 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:
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 | -182.2 ± 2.3 | kJ/mol | Ccb | Speros and Rossini, 1960 | ALS |
| ΔfH°gas | -180.2 | kJ/mol | N/A | Davies and Gilbert, 1941 | Value computed using ΔfHliquid° value of -228.7±1.3 kj/mol from Davies and Gilbert, 1941 and ΔvapH° value of 48.5 kj/mol from Speros and Rossini, 1960.; DRB |
Constant pressure heat capacity of gas
| Cp,gas (J/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 39.17 | 50. | Dorofeeva O.V., 1988 | Recommended values agree with results of statistical calculations [ Miyazawa T., 1958, Chang S., 1970] within their uncertainties. These functions are also reproduced in the reference book [ Frenkel M., 1994].; GT |
| 59.59 | 100. | ||
| 83.80 | 150. | ||
| 109.18 | 200. | ||
| 152.32 | 273.15 | ||
| 168.6 ± 1.0 | 298.15 | ||
| 169.78 | 300. | ||
| 236.37 | 400. | ||
| 297.34 | 500. | ||
| 349.20 | 600. | ||
| 392.71 | 700. | ||
| 429.33 | 800. | ||
| 460.36 | 900. | ||
| 486.74 | 1000. | ||
| 509.26 | 1100. | ||
| 528.54 | 1200. | ||
| 545.08 | 1300. | ||
| 559.33 | 1400. | ||
| 571.64 | 1500. |
Constant pressure heat capacity of gas
| Cp,gas (J/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 237.53 | 400. | Miyazawa T., 1958 | GT |
| 272.29 | 450. |
Condensed phase thermochemistry data
Go To: Top, Gas phase thermochemistry data, Reaction 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:
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 | -230.7 ± 0.92 | kJ/mol | Ccb | Speros and Rossini, 1960 | ALS |
| ΔfH°liquid | -228.7 ± 1.3 | kJ/mol | Ccb | Davies and Gilbert, 1941 | Reanalyzed by Cox and Pilcher, 1970, Original value = -229.6 kJ/mol; ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°liquid | -6276.96 ± 0.92 | kJ/mol | Ccb | Speros and Rossini, 1960 | Corresponding ΔfHºliquid = -230.6 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
| ΔcH°liquid | -6278.9 ± 1.3 | kJ/mol | Ccb | Davies and Gilbert, 1941 | Reanalyzed by Cox and Pilcher, 1970, Original value = -6277.3 ± 0.4 kJ/mol; Corresponding ΔfHºliquid = -228.7 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
| ΔcH°liquid | -6264. ± 2. | kJ/mol | Ccb | Huckel, Kamenz, et al., 1937 | Corresponding ΔfHºliquid = -244. kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
| ΔcH°liquid | -6255.9 | kJ/mol | Ccb | Huckel and Mentzel, 1926 | Corresponding ΔfHºliquid = -251. kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
| ΔcH°liquid | -6268.2 ± 4.6 | kJ/mol | Ccb | Roth and Lasse, 1925 | Corresponding ΔfHºliquid = -239.4 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| S°liquid | 264.93 | J/mol*K | N/A | McCullough, Finke, et al., 1957 | DH |
Constant pressure heat capacity of liquid
| Cp,liquid (J/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 229.17 | 298.15 | Ohnishi, Fujihara, et al., 1989 | DH |
| 229.17 | 298.15 | Shiohama, Ogawa, et al., 1988 | DH |
| 229.17 | 298.15 | Shiohama, Ogawa, et al., 1988, 2 | DH |
| 250.6 | 313. | Gudinowicz, Campbell, et al., 1963 | T = 313 to 423 K.; DH |
| 228.49 | 298.15 | McCullough, Finke, et al., 1957 | T = 10 to 350 K.; DH |
| 226.86 | 298. | Seyer, 1953 | T = 293 to 413 K.; DH |
| 217.72 | 298.15 | Parks and Hatton, 1949 | T = 80 to 298.15 K.; DH |
Reaction thermochemistry data
Go To: Top, Gas phase thermochemistry data, 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. A general reaction search form is also available. Future versions of this site may rely on reaction search pages in place of the enumerated reaction displays seen below.
Individual Reactions
=
By formula: C10H18 = C10H18
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -11.3 | kJ/mol | Eqk | Nuzzi, 1984 | liquid phase; GC |
| ΔrH° | -13.3 | kJ/mol | Eqk | Nuzzi, 1984 | gas phase; GC |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction 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]
Dorofeeva O.V., 1988
Dorofeeva O.V.,
Thermodynamic Properties of Polycyclic Aromatic Hydrocarbons in the Gaseous Phase. Institute for High Temperatures, USSR Academy of Sciences, Preprint No.1-238 (in Russian), Moscow, 1988. [all data]
Miyazawa T., 1958
Miyazawa T.,
Thermodynamic functions for gaseous cis- and trans-decalins from 298 to 1000 K,
J. Am. Chem. Soc., 1958, 80, 60-62. [all data]
Chang S., 1970
Chang S.,
The heats of combustion and strain energies of bicyclo[n.m.0]alkanes,
J. Am. Chem. Soc., 1970, 92, 3109-3118. [all data]
Frenkel M., 1994
Frenkel M.,
Thermodynamics of Organic Compounds in the Gas State, Vol. I, II, Thermodynamics Research Center, College Station, Texas, 1994, 1994. [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]
Nuzzi, 1984
Nuzzi, M.,
cis-Decalin = trans-decalin reaction. Experimental equilibrium constants and thermodynamic functions of its liquid isomers,
Riv. Combust, 1984, 38, 293-297. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, References
- Symbols used in this document:
Cp,gas Constant pressure heat capacity of gas 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°gas Enthalpy of formation of gas at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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