Naphthalene, decahydro-, cis-
- Formula: C10H18
- Molecular weight: 138.2499
- IUPAC Standard InChIKey: NNBZCPXTIHJBJL-AOOOYVTPSA-N
- 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:
- 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
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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
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | -40.45 ± 0.55 | kcal/mol | Ccb | Speros and Rossini, 1960 | ALS |
ΔfH°gas | -40.54 | kcal/mol | N/A | Davies and Gilbert, 1941 | Value computed using ΔfHliquid° value of -219.9±1.3 kj/mol from Davies and Gilbert, 1941 and ΔvapH° value of 50.3 kj/mol from Speros and Rossini, 1960.; DRB |
Constant pressure heat capacity of gas
Cp,gas (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
9.500 | 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 |
14.31 | 100. | ||
19.83 | 150. | ||
25.848 | 200. | ||
36.264 | 273.15 | ||
40.19 ± 0.24 | 298.15 | ||
40.480 | 300. | ||
56.506 | 400. | ||
71.121 | 500. | ||
83.528 | 600. | ||
93.922 | 700. | ||
102.67 | 800. | ||
110.08 | 900. | ||
116.38 | 1000. | ||
121.76 | 1100. | ||
126.36 | 1200. | ||
130.31 | 1300. | ||
133.71 | 1400. | ||
136.65 | 1500. |
Constant pressure heat capacity of gas
Cp,gas (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
56.589 | 400. | Miyazawa T., 1958 | GT |
65.010 | 450. |
IR Spectrum
Go To: Top, Gas phase thermochemistry data, 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 by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Gas Phase Spectrum
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Notice: Concentration information is not available for this spectrum and, therefore, molar absorptivity values cannot be derived.
Additional Data
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Owner | NIST Standard Reference Data Program Collection (C) 2018 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
---|---|
Origin | Sadtler Research Labs Under US-EPA Contract |
State | gas |
Mass spectrum (electron ionization)
Go To: Top, Gas phase thermochemistry data, IR Spectrum, 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 by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Spectrum
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Additional Data
View image of digitized spectrum (can be printed in landscape orientation).
Due to licensing restrictions, this spectrum cannot be downloaded.
Owner | NIST Mass Spectrometry Data Center Collection (C) 2014 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
---|---|
Origin | Japan AIST/NIMC Database- Spectrum MS-NW-2221 |
NIST MS number | 230530 |
Gas Chromatography
Go To: Top, Gas phase thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), 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
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Capillary | HP-1 | 100. | 1096. | Zhang, Li, et al., 1992 | N2; Column length: 25. m; Column diameter: 0.20 mm |
Capillary | HP-1 | 100. | 1096. | Zhang, Li, et al., 1992 | N2; Column length: 25. m; Column diameter: 0.20 mm |
Packed | OV-101 | 120. | 1109. | Litvinenko, Isakova, et al., 1988 | He, Chromaton W AW; Column length: 2.4 m |
Packed | SE-30 | 150. | 1130. | Tiess, 1984 | Ar, Gas Chrom Q (80-100 mesh); Column length: 3. m |
Capillary | OV-101 | 100. | 1097. | Boneva, Papazova, et al., 1983 | N2; Column length: 85. m; Column diameter: 0.28 mm |
Capillary | OV-101 | 100. | 1097. | Boneva, Papazova, et al., 1983 | N2; Column length: 85. m; Column diameter: 0.28 mm |
Capillary | OV-101 | 110. | 1102. | Boneva, Papazova, et al., 1983 | N2; Column length: 85. m; Column diameter: 0.28 mm |
Capillary | OV-101 | 90. | 1090. | Boneva, Papazova, et al., 1983 | N2; Column length: 85. m; Column diameter: 0.28 mm |
Capillary | SE-30 | 70. | 1081.5 | Tóth, 1983 | N2; Column length: 15. m; Column diameter: 0.25 mm |
Capillary | SE-30 | 130. | 1120. | Bredael, 1982 | Column length: 100. m; Column diameter: 0.5 mm |
Capillary | SE-30 | 150. | 1132. | Bredael, 1982 | Column length: 100. m; Column diameter: 0.5 mm |
Capillary | SE-30 | 80. | 1087. | Bredael, 1982 | Column length: 100. m; Column diameter: 0.5 mm |
Capillary | Squalane | 86. | 1101.4 | Macák, Nabivach, et al., 1982 | N2; Column length: 50. m; Column diameter: 0.25 mm |
Capillary | Squalane | 96. | 1106.2 | Macák, Nabivach, et al., 1982 | N2; Column length: 50. m; Column diameter: 0.25 mm |
Capillary | OV-101 | 140. | 1124.8 | Gerasimenko, Kirilenko, et al., 1981 | N2; Column length: 50. m; Column diameter: 0.3 mm |
Capillary | OV-101 | 160. | 1137.7 | Gerasimenko, Kirilenko, et al., 1981 | N2; Column length: 50. m; Column diameter: 0.3 mm |
Capillary | Squalane | 86. | 1101.4 | Nabivach, Bur'yan, et al., 1978 | Column length: 50. m; Column diameter: 0.25 mm |
Capillary | Squalane | 96. | 1106.2 | Nabivach, Bur'yan, et al., 1978 | Column length: 50. m; Column diameter: 0.25 mm |
Capillary | Squalane | 90. | 1100. | Engewald, Epsch, et al., 1976 | N2; Column length: 100. m; Column diameter: 0.23 mm |
Capillary | Squalane | 100. | 1114. | Mitra, Mohan, et al., 1974 | H2; Column length: 50. m; Column diameter: 0.2 mm |
Capillary | Squalane | 120. | 1119. | Schomburg, 1966 | |
Packed | Methyl Silicone | 130. | 1106. | Antheaume and Guiochon, 1965 |
Kovats' RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | OV-101 | 1085. | Hayes and Pitzer, 1982 | 110. m/0.25 mm/0.20 μm, He, 1. K/min; Tstart: 35. C; Tend: 200. C |
Kovats' RI, polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Capillary | PEG-20M | 70. | 1223.0 | Tóth, 1983 | N2; Column length: 30. m; Column diameter: 0.3 mm |
Van Den Dool and Kratz RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-5 | 1089.5 | Song, Lai, et al., 2003 | 30. m/0.25 mm/0.25 μm, He, 2. K/min; Tstart: 40. C; Tend: 310. C |
Capillary | DB-5 | 1096.1 | Song, Lai, et al., 2003 | 30. m/0.25 mm/0.25 μm, He, 4. K/min; Tstart: 40. C; Tend: 310. C |
Capillary | DB-5 | 1100.4 | Song, Lai, et al., 2003 | 30. m/0.25 mm/0.25 μm, He, 6. K/min; Tstart: 40. C; Tend: 310. C |
Capillary | DB-5 | 1071.6 | Xu, van Stee, et al., 2003 | 30. m/0.25 mm/1. μm, He, 2.5 K/min; Tstart: 50. C; Tend: 200. C |
Capillary | DB-5 | 1089.5 | Lai and Song, 1995 | 30. m/0.25 mm/0.25 μm, He, 2. K/min; Tstart: 40. C; Tend: 310. C |
Capillary | DB-5 | 1096.1 | Lai and Song, 1995 | 30. m/0.25 mm/0.25 μm, He, 4. K/min; Tstart: 40. C; Tend: 310. C |
Capillary | DB-5 | 1100.4 | Lai and Song, 1995 | 30. m/0.25 mm/0.25 μm, He, 6. K/min; Tstart: 40. C; Tend: 310. C |
Capillary | Petrocol DH | 1090. | White, Hackett, et al., 1992 | 100. m/0.25 mm/0.5 μm, He, 1. K/min; Tstart: 30. C; Tend: 220. C |
Capillary | Ultra-1 | 1078.85 | Haynes and Pitzer, 1985 | 50. m/0.22 mm/0.33 μm, He, 1. K/min; Tstart: -30. C; Tend: 240. C |
Capillary | Ultra-1 | 1086.83 | Haynes and Pitzer, 1985 | 50. m/0.22 mm/0.33 μm, He, 2. K/min; Tstart: -30. C; Tend: 240. C |
Capillary | Ultra-1 | 1092.00 | Haynes and Pitzer, 1985 | 50. m/0.22 mm/0.33 μm, He, 3. K/min; Tstart: -30. C; Tend: 240. C |
Capillary | Ultra-2 | 1092.50 | Haynes and Pitzer, 1985 | 50. m/0.22 mm/0.33 μm, He, 1. K/min; Tstart: -30. C; Tend: 240. C |
Capillary | Ultra-2 | 1101.09 | Haynes and Pitzer, 1985 | 50. m/0.22 mm/0.33 μm, He, 2. K/min; Tstart: -30. C; Tend: 240. C |
Capillary | Ultra-2 | 1107.06 | Haynes and Pitzer, 1985 | 50. m/0.22 mm/0.33 μm, He, 3. K/min; Tstart: -30. C; Tend: 240. C |
Capillary | OV-101 | 1085. | Hayes and Pitzer, 1981 | 108. m/0.25 mm/0.2 μm, 1. K/min; Tstart: 35. C; Tend: 200. C |
Van Den Dool and Kratz RI, polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Carbowax 20M | 1235. | Whitfield, Shea, et al., 1981 | Column length: 150. m; Column diameter: 0.75 mm; Program: not specified |
Normal alkane RI, non-polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Capillary | Squalane | 120. | 1119. | Rang, Kurashova, et al., 1982 | He; Column length: 50. m; Column diameter: 0.25 mm |
Capillary | Squalane | 110. | 1113. | Papazova and Pankova, 1975 | N2; Column length: 100. m; Column diameter: 0.25 mm |
Capillary | Squalane | 130. | 1123. | Papazova and Pankova, 1975 | N2; Column length: 100. m; Column diameter: 0.25 mm |
Capillary | SE-30 | 150. | 1101. | Vanek, Podrouzková, et al., 1970 | N2; Column length: 50. m; Column diameter: 0.25 mm |
Capillary | SE-30 | 175. | 1116. | Vanek, Podrouzková, et al., 1970 | N2; Column length: 50. m; Column diameter: 0.25 mm |
Packed | Polydimethyl siloxane | 147. | 1124. | Ferrand, 1962 |
Normal alkane RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | HP-5 MS | 1089. | Kotowska, Zalikowski, et al., 2012 | 30. m/0.25 mm/0.25 μm, Helium, 35. C @ 5. min, 3. K/min, 300. C @ 15. min |
Capillary | Petrocol DH | 1093. | Supelco, 2012 | 100. m/0.25 mm/0.50 μm, Helium, 20. C @ 15. min, 15. K/min, 220. C @ 30. min |
Capillary | RTX-1 | 1097. | Arey J.S., Nelson R.K., et al., 2005 | 7. m/0.1 mm/0.4 μm, 35. C @ 5. min, 0.66 K/min; Tend: 180. C |
Capillary | OV-1 | 1103. | Orav, Kailas, et al., 1999 | 2. K/min; Tstart: 50. C; Tend: 160. C |
Capillary | Ultra-1 | 1099. | Elizalde-González, Hutfliess, et al., 1996 | 50. m/0.2 mm/0.33 μm, H2, 3. K/min, 300. C @ 35. min; Tstart: 60. C |
Normal alkane RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | HP-5 MS | 1097. | Kotowska, Zalikowski, et al., 2012 | 30. m/0.25 mm/0.25 μm, Helium; Program: not specified |
Capillary | Polymethylsiloxane, (PMS-20000) | 1082. | Cornwell and Cordano, 2003 | Program: not specified |
Capillary | DB-1 | 1092. | Peng, 1996 | 30. m/0.53 mm/1.5 μm; Program: 40 0C (4 min) 8 0C/min -> 200 0C (1 min) 5 0C/min -> 280 0C (20 min) |
Normal alkane RI, polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Capillary | PEG-20M | 120. | 1276. | Rang, Kurashova, et al., 1982 | He; Column length: 100. m; Column diameter: 0.25 mm |
Capillary | Carbowax 20M | 125. | 1260. | Vanek, Podrouzková, et al., 1970 | N2; Column length: 50. m; Column diameter: 0.25 mm |
Normal alkane RI, polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Carbowax 20M | 1223. | Cornwell and Cordano, 2003 | Program: not specified |
Capillary | DB-Wax | 1232. | Peng, 1996 | 30. m/0.53 mm/1.0 μm; Program: 40 0C (4 min) 4 0C/min -> 200 0C (20 min) |
Capillary | DB-Wax | 1227. | Peng, Yang, et al., 1991 | Program: not specified |
Capillary | DB-Wax | 1232. | Peng, Yang, et al., 1991 | Program: not specified |
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
Frenkel M.,
Thermodynamics of Organic Compounds in the Gas State, Vol. I, II, Thermodynamics Research Center, College Station, Texas, 1994, 1994. [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,
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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,
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Bredael, 1982
Bredael, P.,
Retention indices of hydrocarbons on SE-30,
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Macák, Nabivach, et al., 1982
Macák, J.; Nabivach, V.; Buryan, P.; Sindler, S.,
Dependence of retention indices of alkylbenzenes on their molecular structure,
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. [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,
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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,
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Mitra, Mohan, et al., 1974
Mitra, G.D.; Mohan, G.; Sinha, A.,
Gas chromatographic analysis of complex hydrocarbon mixtures,
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Schomburg, 1966
Schomburg, G.,
Gaschromatographische Retentionsdaten und struktur chemischer verbindungen. III. Alkylverzweigte und ungesättigte cyclische Kohlenwasserstoffe,
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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,
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Hayes and Pitzer, 1982
Hayes, P.C., Jr.; Pitzer, E.W.,
Characterizing petroleum- and shale-derived jet fuel distillates via temperature-programmed Kováts indices,
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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
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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,
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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,
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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,
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Disengaging solutes in shale- and petroleum-derived jet fuels by altering GC programmed temperature rates,
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Hayes and Pitzer, 1981
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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,
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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,
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Papazova and Pankova, 1975
Papazova, D.I.; Pankova, M.C.,
Identification of individual aromatic hydrocarbons in kerosene fraction (b.p. 150-250 °),
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Vanek, Podrouzková, et al., 1970
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Gas chromatographic behaviour of tricyclic saturated hydrocarbons. The relation between the retention indices and the stereochemical structure of the tricyclanes,
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Ferrand, 1962
Ferrand, R.,
Gas phase chromatography using retention indices for the analysis of tars and their hydrogenation products,
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Kotowska, Zalikowski, et al., 2012
Kotowska, U.; Zalikowski, M.; Isidorov, V.A.,
HS-SPME/GC-MS analysis of volatile and semi-volatile organic compounds emitted from municipal sewage sludge,
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. [all data]
Supelco, 2012
Supelco, CatalogNo. 24160-U,
Petrocol DH Columns. Catalog No. 24160-U, 2012, retrieved from http://www.sigmaaldrich.com/etc/medialib/docs/Supelco/Datasheet/1/w97949.Par.0001.File.tmp/w97949.pdf. [all data]
Arey J.S., Nelson R.K., et al., 2005
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,
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. [all data]
Orav, Kailas, et al., 1999
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Notes
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- 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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