Naphthalene, decahydro-
- Formula: C10H18
- Molecular weight: 138.2499
- IUPAC Standard InChIKey: NNBZCPXTIHJBJL-UHFFFAOYSA-N
- CAS Registry Number: 91-17-8
- 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: Bicyclo[4.4.0]decane; Dec; Decahydronaphthalene; Decalin; Dekalin; Naphthan; Perhydronaphthalene; Decanhydronaphthalene; Dekalina; Naphthalane; Naphthane; UN 1147; Decaline; NSC 406139; Cis-decahydronaphthalene
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Condensed phase thermochemistry data
Go To: Top, 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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔcH°liquid | -1488.17 | kcal/mol | Ccb | Gollis, Belenyessy, et al., 1962 | Mixed isomers; Corresponding ΔfHºliquid = -67.173 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°liquid | 63.339 | cal/mol*K | N/A | McCullough, Finke, et al., 1957 | DH |
Constant pressure heat capacity of liquid
Cp,liquid (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
55.468 | 298.15 | Ohnishi, Fujihara, et al., 1989 | DH |
55.497 | 298.15 | Shiohama, Ogawa, et al., 1988 | DH |
55.497 | 298.15 | Shiohama, Ogawa, et al., 1988, 2 | DH |
59.99 | 313. | Gudinowicz, Campbell, et al., 1963 | T = 313 to 423 K.; DH |
52.39 | 311. | Gollis, Belenyessy, et al., 1962, 2 | Temperatures 100, 200, 300°F.; DH |
55.449 | 298.15 | McCullough, Finke, et al., 1957 | T = 10 to 350 K.; DH |
55.810 | 298. | Seyer, 1953 | T = 293 to 343 K.; DH |
52.596 | 298.15 | Parks and Hatton, 1949 | T = 80 to 298.15 K.; DH |
Gas phase ion energetics data
Go To: Top, Condensed phase thermochemistry 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 as indicated in comments:
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
9.14 | EQ | Sieck and Mautner(Meot-Ner), 1982 | LBLHLM |
~9.35 | PE | Bewick, Edwards, et al., 1976 | LLK |
References
Go To: Top, Condensed phase thermochemistry data, Gas phase ion energetics data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Gollis, Belenyessy, et al., 1962
Gollis, M.H.; Belenyessy, L.I.; Gudzinowicz, B.J.; Koch, S.D.; Smith, J.O.; Wineman, R.J.,
Evaluation of pure hydrocarbons as jet fuels,
J. Chem. Eng. Data, 1962, 7, 331-316. [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]
Gollis, Belenyessy, et al., 1962, 2
Gollis, M.H.; Belenyessy, L.I.; Gudzinowicz, B.J.; Koch, S.D.; Smith, J.O.; Wineman, R.J.,
Evaluations of pure hydrocarbons as Jet Fuels,
J. Chem. Eng. Data, 1962, 7, 311-316. [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]
Sieck and Mautner(Meot-Ner), 1982
Sieck, L.W.; Mautner(Meot-Ner), M.,
Ionization energies and entropies of cycloalkanes. Kinetics of free energy controlled charge-transfer reactions,
J. Phys. Chem., 1982, 86, 3646. [all data]
Bewick, Edwards, et al., 1976
Bewick, A.; Edwards, C.J.; Jones, S.R.; Mellor, J.M.,
The electrochemical difunctionalisation of saturated hydrocarbons,
Tetrahedron Lett., 1976, 631. [all data]
Notes
Go To: Top, Condensed phase thermochemistry data, Gas phase ion energetics data, References
- Symbols used in this document:
Cp,liquid Constant pressure heat capacity of liquid S°liquid Entropy of liquid at standard conditions ΔcH°liquid Enthalpy of combustion of liquid at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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