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, Phase change data, Henry's Law data, Gas phase ion energetics 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 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 |
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
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 463.2 | K | N/A | Aldrich Chemical Company Inc., 1990 | BS |
Tboil | 465. | K | N/A | Greensfelder and Voge, 1945 | Uncertainty assigned by TRC = 5. K; TRC |
Tboil | 465. | K | N/A | Larsen, Thorpe, et al., 1942 | Uncertainty assigned by TRC = 2. K; TRC |
Tboil | 445. | K | N/A | Ross and Leather, 1906 | Uncertainty assigned by TRC = 10. K; TRC |
Tboil | 461. | K | N/A | Leroux, 1904 | Uncertainty assigned by TRC = 6. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 149. | K | N/A | Herz and Schuftan, 1922 | Uncertainty assigned by TRC = 2.5 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 645. | K | N/A | Glaser and Ruland, 1957 | Uncertainty assigned by TRC = 2. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Pc | 20.53 | atm | N/A | Glaser and Ruland, 1957 | Uncertainty assigned by TRC = 1.5000 atm; TRC |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
3.4450 | 242.78 | McCullough, Finke, et al., 1957 | DH |
0.5280 | 230.1 | Parks and Hatton, 1949 | DH |
Entropy of fusion
ΔfusS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
14.19 | 242.78 | McCullough, Finke, et al., 1957 | DH |
2.3 | 230.1 | Parks and Hatton, 1949 | DH |
Henry's Law 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 by: Rolf Sander
Henry's Law constant (water solution)
kH(T) = k°H exp(d(ln(kH))/d(1/T) ((1/T) - 1/(298.15 K)))
k°H = Henry's law constant for solubility in water at 298.15 K (mol/(kg*bar))
d(ln(kH))/d(1/T) = Temperature dependence constant (K)
k°H (mol/(kg*bar)) | d(ln(kH))/d(1/T) (K) | Method | Reference |
---|---|---|---|
0.0072 | 4100. | X | N/A |
Gas phase ion energetics data
Go To: Top, Condensed phase thermochemistry data, Phase change data, Henry's Law 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 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 |
IR Spectrum
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Data compiled by: Coblentz Society, Inc.
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Mass spectrum (electron ionization)
Go To: Top, Condensed phase thermochemistry data, Phase change data, Henry's Law data, Gas phase ion energetics data, IR Spectrum, 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
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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-2843 |
NIST MS number | 231649 |
References
Go To: Top, Condensed phase thermochemistry data, Phase change data, Henry's Law data, Gas phase ion energetics data, IR Spectrum, 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.
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]
Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc.,
Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [all data]
Greensfelder and Voge, 1945
Greensfelder, B.S.; Voge, H.H.,
Catalytic Cracking of Pure Hydrodarbons. Cracking of Naphthenes,
Ind. Eng. Chem., 1945, 37, 1038-43. [all data]
Larsen, Thorpe, et al., 1942
Larsen, R.G.; Thorpe, R.E.; Armfield, F.A.,
Oxidation Characteristics of Pure Hydrocarbons,
Ind. Eng. Chem., 1942, 34, 183. [all data]
Ross and Leather, 1906
Ross, R.; Leather, J.P.,
Analyst (London), 1906, 31, 284. [all data]
Leroux, 1904
Leroux, H.,
Naphthalene tetrahydride and decahydride,
C. R. Hebd. Seances Acad. Sci., 1904, 139, 672-674. [all data]
Herz and Schuftan, 1922
Herz, W.; Schuftan, P.,
Physical-chemical investigations of tetralin and decalin.,
Z. Phys. Chem. (Leipzig), 1922, 101, 269. [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]
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, Phase change data, Henry's Law data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), References
- Symbols used in this document:
Cp,liquid Constant pressure heat capacity of liquid Pc Critical pressure S°liquid Entropy of liquid at standard conditions Tboil Boiling point Tc Critical temperature Tfus Fusion (melting) point d(ln(kH))/d(1/T) Temperature dependence parameter for Henry's Law constant k°H Henry's Law constant at 298.15K ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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