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, Condensed phase thermochemistry 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 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. |
Condensed phase thermochemistry 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: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°liquid | -52.45 ± 0.22 | kcal/mol | Ccb | Speros and Rossini, 1960 | |
ΔfH°liquid | -52.55 ± 0.32 | kcal/mol | Ccb | Davies and Gilbert, 1941 | Reanalyzed by Cox and Pilcher, 1970, Original value = -52.75 kcal/mol |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -1502.92 ± 0.22 | kcal/mol | Ccb | Speros and Rossini, 1960 | Corresponding ΔfHºliquid = -52.43 kcal/mol (simple calculation by NIST; no Washburn corrections) |
ΔcH°liquid | -1502.80 ± 0.30 | kcal/mol | Ccb | Davies and Gilbert, 1941 | Reanalyzed by Cox and Pilcher, 1970, Original value = -1502.4 ± 0.1 kcal/mol; Corresponding ΔfHºliquid = -52.55 kcal/mol (simple calculation by NIST; no Washburn corrections) |
ΔcH°liquid | -1499.9 | kcal/mol | Ccb | Huckel and Mentzel, 1926 | Corresponding ΔfHºliquid = -55.4 kcal/mol (simple calculation by NIST; no Washburn corrections) |
ΔcH°liquid | -1501.18 ± 0.97 | kcal/mol | Ccb | Roth and Lasse, 1925 | Corresponding ΔfHºliquid = -54.17 kcal/mol (simple calculation by NIST; no Washburn corrections) |
Gas phase ion energetics 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 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
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
IE (evaluated) | 9.32 ± 0.05 | eV | N/A | N/A | L |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
9.32 ± 0.05 | PI | Mikaya and Zaikin, 1980 | LLK |
9.427 ± 0.003 | EI | Mikaya and Zaikin, 1980 | LLK |
9.40 | PE | Dewar and Worley, 1969 | RDSH |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C6H10+ | 10.89 ± 0.02 | ? | EI | Natalis, 1962 | RDSH |
C7H12+ | 10.72 ± 0.02 | C3H6 | EI | Natalis, 1962 | RDSH |
References
Go To: Top, Gas phase thermochemistry data, 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.
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]
Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G.,
Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]
Huckel and Mentzel, 1926
Huckel, W.; Mentzel, R.,
Zur Stereochemie bicyclischer Ringsteme II. Die Stereoisomerie des Dekahydronaphtalins und seiner Derivate II. Stereoisomere β-substituierte Dekaline,
Ann., 1926, 451, 109-132. [all data]
Roth and Lasse, 1925
Roth, W.A.; Lasse, R.,
Verbrennungswarme der Dekahydro-naphthaline und der Dekalone,
Ann., 1925, 441, 48-53. [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]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance energy Cp,gas Constant pressure heat capacity of gas IE (evaluated) Recommended ionization energy ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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