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:
  • Gas phase thermochemistry data
  • Phase change data
  • Gas phase ion energetics data
  • Mass spectrum (electron ionization)
  • References
  • Notes
• Other data available:
  • Condensed phase thermochemistry data
  • Reaction thermochemistry data
  • IR Spectrum
  • Gas Chromatography
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
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Gas 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
DRB - Donald R. Burgess, Jr.
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow

Constant pressure heat capacity of gas

Constant pressure heat capacity of gas

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

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 evaluated as indicated in comments:
L - Sharon G. Lias

Data compiled as indicated in comments:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

Ionization energy determinations

Appearance energy determinations

Mass spectrum (electron ionization)

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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

Spectrum

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Additional Data

References

Go To: Top, Gas phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), 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]

McCullough, Finke, et al., 1957
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
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]

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-decahydronaphthalene, J. Am. Chem. Soc., 1949, 71, 2773-2775. [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]

McCullough, Finke, et al., 1957, 2
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]

Mikaya and Zaikin, 1980
Mikaya, A.I.; Zaikin, V.G., Determination of the difference in enthalpies of formation of the cis- and trans-isomers of bicyclo[4.3.0]nonane and bicyclo[4.4.0]decane using appearance potentials, Izv. Akad. Nauk SSSR, Ser. Khim., 1980, 6, 1286. [all data]

Dewar and Worley, 1969
Dewar, M.J.S.; Worley, S.D., Photoelectron spectra of molecules. I. Ionization potentials of some organic molecules and their interpretation, J. Chem. Phys., 1969, 50, 654. [all data]

Natalis, 1962
Natalis, P., Note sur le comportement des isomeres cis et trans de la decaline soumis a l'impact electronique, Bull. Soc. Roy. Sci. Liege, 1962, 31, 803. [all data]

Notes

Go To: Top, Gas phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), References

• Symbols used in this document:
  

  AE	Appearance energy
  Cp,gas	Constant pressure heat capacity of gas
  IE (evaluated)	Recommended ionization energy
  Tboil	Boiling point
  Tc	Critical temperature
  Tfus	Fusion (melting) point
  Ttriple	Triple point temperature
  ΔHtrs	Enthalpy of phase transition
  ΔStrs	Entropy of phase transition
  ΔfH°gas	Enthalpy of formation of gas 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
  ΔvapH°	Enthalpy of vaporization at standard conditions

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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