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- Copy

  
• IUPAC Standard InChIKey: NNBZCPXTIHJBJL-MGCOHNPYSA-N Copy
• 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:
  • Naphthalene, decahydro-, cis-
  • Naphthalene, decahydro-
• 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
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Condensed phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry data
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Gas phase ion energetics data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • Gas Chromatography
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
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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

Constant pressure heat capacity of liquid

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
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
AC - William E. Acree, Jr., James S. Chickos
DH - Eugene S. Domalski and Elizabeth D. Hearing
CAL - James S. Chickos, William E. Acree, Jr., Joel F. Liebman, Students of Chem 202 (Introduction to the Literature of Chemistry), University of Missouri -- St. Louis

Reduced pressure boiling point

Enthalpy of vaporization

Antoine Equation Parameters

log₁₀(P) = A − (B / (T + C))
    P = vapor pressure (bar)
    T = temperature (K)

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Enthalpy of sublimation

Enthalpy of fusion

Entropy of fusion

Entropy of fusion

Enthalpy of phase transition

Entropy of phase transition

Reaction thermochemistry data

Go To: Top, Condensed phase thermochemistry data, Phase change 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

References

Go To: Top, Condensed phase thermochemistry data, Phase change 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]

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]

McCullough, Finke, et al., 1957, 2
McCullough, J.P.; Finke, H.L.; Messerly, J.F.; Todd, S.S.; Kincheloe, T.C.; Waddington, G., The Low-Temperature Thermodynamic Properties of Naphthalene, 1-Methylnaphthalene, 2-Methylnaphthalene, 1,2,3,4-tetrahydro- naphthalene, trans-decahydronaphthalene and cis-Decahydronaphthalene, J. Phys. Chem., 1957, 61, 1105. [all data]

Parks and Hatton, 1949, 2
Parks, G.S.; Hatton, J.A., Thermal Data on Organic Compounds. XXIV. The Heat Capacities, Entropies and Free Energies of cis- and trans-Decahydronapthalene, J. Am. Chem. Soc., 1949, 71, 2773-5. [all data]

Daubert, 1996
Daubert, T.E., Vapor-Liquid Critical Properties of Elements and Compounds. 5. Branched Alkanes and Cycloalkanes, J. Chem. Eng. Data, 1996, 41, 365-372. [all data]

Cheng, McCoubrey, et al., 1962
Cheng, D.C.H.; McCoubrey, J.C.; Phillips, D.G., Critical Temperatures of Some Organic Cyclic Compounds, Trans. Faraday Soc., 1962, 58, 224. [all data]

Glaser and Ruland, 1957
Glaser, F.; Ruland, H., Untersuchungsen über dampfdruckkurven und kritische daten einiger technisch wichtiger organischer substanzen, Chem. Ing. Techn., 1957, 29, 772. [all data]

Bondi, 1963
Bondi, A., Heat of Siblimation of Molecular Crystals: A Catalog of Molecular Structure Increments., J. Chem. Eng. Data, 1963, 8, 3, 371-381, https://doi.org/10.1021/je60018a027 . [all data]

Chickos, Hosseini, et al., 1993
Chickos, James S.; Hosseini, Sarah; Hesse, Donald G.; Liebman, Joel F., Heat capacity corrections to a standard state: a comparison of new and some literature methods for organic liquids and solids, Struct Chem, 1993, 4, 4, 271-278, https://doi.org/10.1007/BF00673701 . [all data]

Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc., Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 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]

Camin and Rossini, 1955
Camin, David L.; Rossini, Frederick D., Physical Properties of Fourteen API Research Hydrocarbons, C ₉ to C ₁₅, J. Phys. Chem., 1955, 59, 11, 1173-1179, https://doi.org/10.1021/j150533a014 . [all data]

Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D., Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III, J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985 . [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, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, References

• Symbols used in this document:
  

  Cp,liquid	Constant pressure heat capacity of liquid
  S°liquid	Entropy of liquid at standard conditions
  Tboil	Boiling point
  Tc	Critical temperature
  Tfus	Fusion (melting) point
  Ttriple	Triple point temperature
  ΔHtrs	Enthalpy of phase transition
  ΔStrs	Entropy of phase transition
  ΔcH°liquid	Enthalpy of combustion of liquid at standard conditions
  ΔfH°liquid	Enthalpy of formation of liquid at standard conditions
  ΔfusH	Enthalpy of fusion
  ΔfusS	Entropy of fusion
  ΔrH°	Enthalpy of reaction at standard conditions
  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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