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
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• Information on this page:
  • Gas phase thermochemistry data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • Gas Chromatography
  • References
  • Notes
• Other data available:
  • Condensed phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry data
  • Gas phase ion energetics data
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
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Gas phase thermochemistry data

Go To: Top, IR Spectrum, Mass spectrum (electron ionization), 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:
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

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

• LIQUID (NEAT); DOW KBr FOREPRISM-GRATING; DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 4 cm^-1 resolution
• SOLUTION; CARY 90 (GRATING); DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 2 cm^-1 resolution
• SOLUTION (10% IN CCl4 FOR 3800-1335 AND 10% IN CS2 FOR 1335-470 CM^-1) VS. SOLVENT; DOW KBr FOREPRISM-GRATING; DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 4 cm^-1 resolution

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

• gas; HP-GC/MS/IRD

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

Gas Chromatography

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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

Kovats' RI, non-polar column, isothermal

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Kovats' RI, non-polar column, temperature ramp

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Kovats' RI, non-polar column, custom temperature program

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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, non-polar column, custom temperature program

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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, Gas phase thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, 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
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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
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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]

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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]

Shlyakhov, Anvaer, et al., 1975
Shlyakhov, A.F.; Anvaer, B.I.; Zolotareva, O.V.; Romina, N.N.; Novikova, N.V.; Koreshkova, R.I., On the possibility of group indentification of hydrocarbons by gas chromatography from temperature coefficients of retention indices, Zh. Anal. Khim., 1975, 30, 788-792. [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]

Takeda and Yamamoto, 1972
Takeda, K.; Yamamoto, S., Gas chromatographic identification of 2,6-disubstituted-trans-decalins using retention indices, Chem. Pharm. Bull., 1972, 20, 6, 1125-1130, https://doi.org/10.1248/cpb.20.1125 . [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]

Louis, 1971
Louis, R., Kovats-index-tafeln zur gaschromatographischen analyse von kohlenwasserstoffgemischen, Erdoel Kohle Erdgas Petrochem., 1971, 24, 2, 88-94. [all data]

Haagen-Smit Laboratory, 1997
Haagen-Smit Laboratory, Procedure for the detailed hydrocarbon analysis of gasolines by single column high efficiency (capillary) column gas chromatography, SOP NO. MLD 118, Revision No. 1.1, California Environmental Protection Agency, Air Resources Board, El Monte, California, 1997, 22. [all data]

Kallio, Jussila, et al., 2006
Kallio, M.; Jussila, M.; Rissanen, T.; Anttila, P.; Hartonen, K.; Reissell, A.; Vreuls, R.; Adahchour, M.; Hyotylainen, T., Comprehensive two-dimensional gas chromatography coupled to time-of-flight mass spectrometry in the identification of organic compounds in atmospheric aerosols from coniferous forest, J. Chromatogr. A, 2006, 1125, 2, 234-243, https://doi.org/10.1016/j.chroma.2006.05.050 . [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]

Sun and Stremple, 2003
Sun, G.; Stremple, P., Retention index characterization of flavor, fragrance, and many other compounds on DB-1 and DB-XLB, 2003, retrieved from http://www.chem.agilent.com/cag/cabu/pdf/b-0279.pdf. [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]

Steward and Pitzer, 1988
Steward, E.M.; Pitzer, E.W., Gas Chromatographic Analyses of Complex Hydrocarbon Mixtures Void of n-Paraffin Retention Index Markers Using Joint Mass Spectral and Retention Index Libraries, J. Chromatogr. Sci., 1988, 26, 5, 218-222, https://doi.org/10.1093/chromsci/26.5.218 . [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]

Yasuhara, Shiraishi, et al., 1997
Yasuhara, A.; Shiraishi, H.; Nishikawa, M.; Yamamoto, T.; Uehiro, T.; Nakasugi, O.; Okumura, T.; Kenmotsu, K.; Fukui, H.; Nagase, M.; Ono, Y.; Kawagoshi, Y.; Baba, K.; Noma, Y., Determination of organic components in leachates from hazardous waste disposal sites in Japan by gas chromatography-mass spectrometry, J. Chromatogr. A, 1997, 774, 1-2, 321-332, https://doi.org/10.1016/S0021-9673(97)00078-2 . [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]

Nabivach and Gerasimenko, 1996
Nabivach, V.M.; Gerasimenko, V.A., Gas chromatographic retention characteristics of bicyclic aromatic hydrocarbons, Coke and Chemistry (Rus), 1996, 6, 27-31. [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]

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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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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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Pontes, de Olivera, et al., 2007
Pontes, W.J.T.; de Olivera, J.C.G.; da Camara, C.A.G.; Lopes, A.C.H.R.; Gondim Jr.; de Olivera, J.V.; Barros, R.; Schwartz, M.O.E., Chemical composition and acaridical activity of the leaf and fruit essential oils of Protium heptaphyllum (Aubl.) Marchand (Burseraceae), Acta Amazonica, 2007, 37, 1, 103-110, https://doi.org/10.1590/S0044-59672007000100012 . [all data]

Orav, Kailas, et al., 1999
Orav, A.; Kailas, T.; Muurisepp, M.; Kann, J., Composition of the oil from waste tires. 2. Fraction boiling at 160-180 0C, Proc. Estonian Acad. Sci. Chem., 1999, 48, 3, 136-140. [all data]

Elizalde-González, Hutfliess, et al., 1996
Elizalde-González, M.P.; Hutfliess, M.; Hedden, K., Retention index system, adsorption characteristics, and sructure correlations of polycyclic aromatic hydrocarbons in fuels, J. Hi. Res. Chromatogr., 1996, 19, 6, 345-352, https://doi.org/10.1002/jhrc.1240190608 . [all data]

Cornwell and Cordano, 2003
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]

Waggott and Davies, 1984
Waggott, A.; Davies, I.W., Identification of organic pollutants using linear temperature programmed retention indices (LTPRIs) - Part II, 1984, retrieved from http://dwi.defra.gov.uk/research/completed-research/reports/dwi0383.pdf. [all data]

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Peng, C.T., Gas chromatographic identification of aromatic hydrocarbons in Liquid Scintillation Spectrometry, Cook, G.T.; Harkness, D.D.; MacKenzie, A.B.; Miller, B.F.; Scott, E.M., ed(s)., 1996, 221-232. [all data]

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, Gas phase thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, References

• Symbols used in this document:
  

  Cp,gas	Constant pressure heat capacity of gas
  ΔfH°gas	Enthalpy of formation of gas at standard conditions

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