Naphthalene, decahydro-, cis-

• 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-AOOOYVTPSA-N Copy
• CAS Registry Number: 493-01-6
• 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-, trans-
  • Naphthalene, decahydro-
• Other names: cis-Bicyclo[4.4.0]Decane; cis-Decahydronaphthalene; cis-Decalin; cis-Perhydronaphthalene; Decahydronaphthalene, (Z)-; c-Decahydronaphthalene; c-Decalin; Decahydronaphthalene, cis; (Z)-Decahydronaphthalene; Bicyclo[4.4.0]decane, isomer # 2; cis-Decahydronapthalene
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Phase change data
  • Gas phase ion energetics data
  • Gas Chromatography
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Reaction thermochemistry data
  • IR Spectrum
  • Mass spectrum (electron ionization)
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
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Phase change data

Go To: Top, Gas phase ion energetics 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:
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

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

Gas phase ion energetics data

Go To: Top, 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 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

Gas Chromatography

Go To: Top, Phase change data, Gas phase ion energetics 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: NIST Mass Spectrometry Data Center, William E. Wallace, director

Kovats' RI, non-polar column, isothermal

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Kovats' RI, non-polar column, temperature ramp

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Kovats' RI, polar column, isothermal

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Van Den Dool and Kratz RI, non-polar column, temperature ramp

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Van Den Dool and Kratz RI, polar column, custom temperature program

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Normal alkane RI, non-polar column, isothermal

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Normal alkane RI, non-polar column, temperature ramp

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Normal alkane RI, non-polar column, custom temperature program

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Normal alkane RI, polar column, isothermal

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Normal alkane RI, polar column, custom temperature program

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References

Go To: Top, Phase change data, Gas phase ion energetics data, Gas Chromatography, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

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]

Matzik and Schneider, 1985
Matzik, I.; Schneider, G.M., Fluid phase equilibria of binary mixtures of sulfur hexafluoride with octane, nonane, hendecane, and cis-decahydronaphthalene at temperature between 280 K and 440 K and at pressures up to 140 MPa, Ber. Bunsen-Ges. Phys. Chem., 1985, 89, 551. [all data]

Pak and Kay, 1972
Pak, S.C.; Kay, W.B., Gas-Liquid Critical Temperatures of Mixtures. Benzene + n-Alkanes and Hexafluorobenzene + n-Alkanes, Ind. Eng. Chem. Fundam., 1972, 11, 255. [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]

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]

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]

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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]

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]

Zhang, Li, et al., 1992
Zhang, M.J.; Li, S.D.; Chen, B.J., Compositional studies of high-temperature coal tar by GC/FTIR analysis of light oil fractions, Chromatographia, 1992, 33, 3/4, 138-146, https://doi.org/10.1007/BF02275894 . [all data]

Litvinenko, Isakova, et al., 1988
Litvinenko, G.S.; Isakova, L.A.; Rubanyk, N.N., Quantitative correlation between structure of stereoisomeric saturated cyclic compounds and gas-chromatographic retention indices. I. Methysubstituted, Izv. AN Kaz. SSR, Ser. Khim., 1988, 5, 54-66. [all data]

Tiess, 1984
Tiess, D., Gaschromatographische Retentionsindices von 125 leicht- bis mittelflüchtigen organischen Substanzen toxikologisch-analytischer Relevanz auf SE-30, Wiss. Z. Wilhelm-Pieck-Univ. Rostock Math. Naturwiss. Reihe, 1984, 33, 6-9. [all data]

Boneva, Papazova, et al., 1983
Boneva, St.; Papazova, D.; Dimov, N., Retention Indices of aromatic hydrocarbons on glass and metal capillary columns with stationary phase OV-101, Jahrb. Chem. Tech. Hochschule Burgas, 1983, 18, 143-148. [all data]

Tóth, 1983
Tóth, T., Use of capillary gas chromatography in collecting retention and chemical information for the analysis of complex petrochemical mixtures, J. Chromatogr., 1983, 279, 157-165, https://doi.org/10.1016/S0021-9673(01)93614-3 . [all data]

Bredael, 1982
Bredael, P., Retention indices of hydrocarbons on SE-30, J. Hi. Res. Chromatogr. Chromatogr. Comm., 1982, 5, 6, 325-328, https://doi.org/10.1002/jhrc.1240050610 . [all data]

Macák, Nabivach, et al., 1982
Macák, J.; Nabivach, V.; Buryan, P.; Sindler, S., Dependence of retention indices of alkylbenzenes on their molecular structure, J. Chromatogr., 1982, 234, 2, 285-302, https://doi.org/10.1016/S0021-9673(00)81867-1 . [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]

Nabivach, Bur'yan, et al., 1978
Nabivach, V.M.; Bur'yan, P.; Matsak, I., Retention indices of aromatic hydrocarbons on a squalane capillary column, Zh. Anal. Khim., 1978, 33, 7, 1108-1113. [all data]

Engewald, Epsch, et al., 1976
Engewald, W.; Epsch, K.; Welsch, Th.; Graefe, J., Molekülstruktur und Retentionsverhalten. VI. Retentionsverhalten von bicycle[n.m.0]alkanen bei der gas-adsorptions- und gas-verteilungs-chromatographie, J. Chromatogr., 1976, 119, 119-128, https://doi.org/10.1016/S0021-9673(00)86776-X . [all data]

Mitra, Mohan, et al., 1974
Mitra, G.D.; Mohan, G.; Sinha, A., Gas chromatographic analysis of complex hydrocarbon mixtures, J. Chromatogr. A, 1974, 91, 633-648, https://doi.org/10.1016/S0021-9673(01)97944-0 . [all data]

Schomburg, 1966
Schomburg, G., Gaschromatographische Retentionsdaten und struktur chemischer verbindungen. III. Alkylverzweigte und ungesättigte cyclische Kohlenwasserstoffe, J. Chromatogr., 1966, 23, 18-41, https://doi.org/10.1016/S0021-9673(01)98653-4 . [all data]

Antheaume and Guiochon, 1965
Antheaume, J.; Guiochon, G., Application de la chromatographie en phase gazeuse à l'étude de la composition des fractions moyennes d'un brut pétrolier, Bull. Soc. Chim. Fr., 1965, 2, 298-307. [all data]

Hayes and Pitzer, 1982
Hayes, P.C., Jr.; Pitzer, E.W., Characterizing petroleum- and shale-derived jet fuel distillates via temperature-programmed Kováts indices, J. Chromatogr., 1982, 253, 179-198, https://doi.org/10.1016/S0021-9673(01)88376-X . [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]

Xu, van Stee, et al., 2003
Xu, X.; van Stee, L.L.P.; Williams, J.; Beens, J.; Adahchour, M.; Vreuls, R.J.J.; Brinkman, U.A.Th.; Lelieveld, J., Comprehensive two-dimensional gas chromatography (GC×GC) measurements of volatile organic compounds in the atmosphere, Atmos. Chem. Phys., 2003, 3, 3, 665-682, https://doi.org/10.5194/acp-3-665-2003 . [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]

White, Hackett, et al., 1992
White, C.M.; Hackett, J.; Anderson, R.R.; Kail, S.; Spock, P.S., Linear temperature programmed retention indices of gasoline range hydrocarbons and chlorinated hydrocarbons on cross-linked polydimethylsiloxane, J. Hi. Res. Chromatogr., 1992, 15, 2, 105-120, https://doi.org/10.1002/jhrc.1240150211 . [all data]

Haynes and Pitzer, 1985
Haynes, P.C., Jr.; Pitzer, E.W., Disengaging solutes in shale- and petroleum-derived jet fuels by altering GC programmed temperature rates, J. Hi. Res. Chromatogr. Chromatogr. Comm., 1985, 8, 5, 230-242, https://doi.org/10.1002/jhrc.1240080504 . [all data]

Hayes and Pitzer, 1981
Hayes, P.C., Jr.; Pitzer, E.W., Kovats indices as a tool in characterizing hydrocarbon fuels in temperature programmed glass capillary gas chromatography. Part 1. Qualitative identification, Inhouse rpt. for Air Force Wright Aeronautical Labs., Air Force Wright Aeronautical Labs., Wright-Patterson AFB, Ohio, 1981, 75. [all data]

Whitfield, Shea, et al., 1981
Whitfield, F.B.; Shea, S.R.; Gillen, K.J.; Shaw, K.J., Volatile components from the roots of Acacia pulchella R.Br. and their effect on Phytophthora cinnamomi rands, Aust. J. Bot., 1981, 29, 2, 195-208, https://doi.org/10.1071/BT9810195 . [all data]

Rang, Kurashova, et al., 1982
Rang, S.; Kurashova, E.Kh.; Musaev, I.A.; Strenze, T.V.; Joepera, E.; Eisen, O.; Sanin, P.I., Gas-chromatographic characteristics of stereoisomers of the bicyblo[4.4.0]decane series, Neftekhimiya, 1982, 22, 3, 303-308. [all data]

Papazova and Pankova, 1975
Papazova, D.I.; Pankova, M.C., Identification of individual aromatic hydrocarbons in kerosene fraction (b.p. 150-250 °), J. Chromatogr., 1975, 105, 2, 411-414, https://doi.org/10.1016/S0021-9673(01)82276-7 . [all data]

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Vanek, J.; Podrouzková, B.; Landa, S., Gas chromatographic behaviour of tricyclic saturated hydrocarbons. The relation between the retention indices and the stereochemical structure of the tricyclanes, J. Chromatogr., 1970, 52, 77-86, https://doi.org/10.1016/S0021-9673(01)96546-X . [all data]

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Ferrand, R., Gas phase chromatography using retention indices for the analysis of tars and their hydrogenation products, Journees internationales d'etude des methodes de separation immediate at de chromatographie; Org. sur l'initiative du IX., 1962, 132-140. [all data]

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Arey J.S.; Nelson R.K.; Xu L.; Reddy C.M., Using comprehensive two-dimensional gas chromatography retention indices to estimate environmental partitioning properties for a complete set of diesel fuel hydrocarbons, Anal. Chem., 2005, 77, 22, 7172-7182, https://doi.org/10.1021/ac051051n . [all data]

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Cornwell, E.; Cordano, G., Nueva proposicion para predecir datos de retencion obtenidos mediante cromatografia de gases de hidrocarburos derivados de las naftas, Revista de la Sociedad Quimica de Mexico, 2003, 47, 1, 38-43. [all data]

Peng, 1996
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Peng, Yang, et al., 1991
Peng, C.T.; Yang, Z.C.; Ding, S.F., Prediction of rentention idexes. II. Structure-retention index relationship on polar columns, J. Chromatogr., 1991, 586, 1, 85-112, https://doi.org/10.1016/0021-9673(91)80028-F . [all data]

Notes

Go To: Top, Phase change data, Gas phase ion energetics data, Gas Chromatography, References

• Symbols used in this document:
  

  AE	Appearance energy
  IE (evaluated)	Recommended ionization energy
  Pc	Critical pressure
  Tboil	Boiling point
  Tc	Critical temperature
  Tfus	Fusion (melting) point
  Ttriple	Triple point temperature
  ΔfusH	Enthalpy 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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