Naphthalene, 1,2,3,4-tetrahydro-
- Formula: C10H12
- Molecular weight: 132.2023
- IUPAC Standard InChI: InChI=1S/C10H12/c1-2-6-10-8-4-3-7-9(10)5-1/h1-2,5-6H,3-4,7-8H2
- IUPAC Standard InChIKey: CXWXQJXEFPUFDZ-UHFFFAOYSA-N
- CAS Registry Number: 119-64-2
- 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. - Isotopologues:
- Other names: Tetralin; Benzocyclohexane; Tetrahydronaphthalene; Tetraline; Tetranap; 1,2,3,4-Tetrahydronaphthalene; Naphthalene-1,2,3,4-tetrahydride; δ(5,7,9)-Naphthantriene; Bacticin; Tetralina; NSC 77451; tetralene
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Gas phase thermochemistry 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:
DRB - Donald R. Burgess, Jr.
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°gas | 7.17 | kcal/mol | N/A | Good and Lee, 1976 | Value computed using ΔfHliquid° value of -28.6±1.0 kj/mol from Good and Lee, 1976 and ΔvapH° value of 58.6 kj/mol from Boyd, Sanwal, et al., 1971.; DRB |
| ΔfH°gas | 6.22 ± 0.47 | kcal/mol | Ccb | Boyd, Sanwal, et al., 1971 | Reanalyzed by Pedley, Naylor, et al., 1986, Original value = 5.29 ± 0.81 kcal/mol; ALS |
Constant pressure heat capacity of gas
| Cp,gas (cal/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 9.443 | 50. | Dorofeeva O.V., 1988 | Recommended values were calculated statistically mechanically using force field approximation for polycyclic aromatic hydrocarbons to estimate the needed vibrational frequencies (see also [ Dorofeeva O.V., 1986]). These functions are reproduced in the reference book [ Frenkel M., 1994]. Values of S(298.15 K)=368.6 and Cp(298.15 K)=146.6 J/mol*K were calculated using molecular constants estimated by molecular mechanics [ Boyd R.H., 1971]. Discrepancies with semiempirical calculation [ Szekely, 1955] amount to 14 and 6 J/mol*K for S and Cp at 298.15 K. Cp(298.15 K) calculated by semiempirical calculation [ Vvedenskii A.A., 1957] agrees well with value recommended here.; GT |
| 13.23 | 100. | ||
| 17.98 | 150. | ||
| 23.49 | 200. | ||
| 32.737 | 273.15 | ||
| 36.08 ± 0.48 | 298.15 | ||
| 36.324 | 300. | ||
| 49.391 | 400. | ||
| 60.782 | 500. | ||
| 70.179 | 600. | ||
| 77.894 | 700. | ||
| 84.288 | 800. | ||
| 89.646 | 900. | ||
| 94.168 | 1000. | ||
| 98.009 | 1100. | ||
| 101.28 | 1200. | ||
| 104.09 | 1300. | ||
| 106.50 | 1400. | ||
| 108.58 | 1500. |
Condensed phase thermochemistry data
Go To: Top, Gas 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:
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 |
|---|---|---|---|---|---|
| ΔfH°liquid | -6.83 ± 0.25 | kcal/mol | Ccb | Good and Lee, 1976 | ALS |
| ΔfH°liquid | -7.79 ± 0.52 | kcal/mol | Ccb | Boyd, Sanwal, et al., 1971 | Reanalyzed by Pedley, Naylor, et al., 1986, Original value = -7.91 ± 0.51 kcal/mol; ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°liquid | -1343.58 ± 0.21 | kcal/mol | Ccb | Good and Lee, 1976 | Corresponding ΔfHºliquid = -6.82 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
| ΔcH°liquid | -1342.61 ± 0.51 | kcal/mol | Ccb | Boyd, Sanwal, et al., 1971 | Corresponding ΔfHºliquid = -7.79 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
| ΔcH°liquid | -1338.1 | kcal/mol | Ccb | Karo, McLaughlin, et al., 1953 | Corrected from net heat of combustion; Corresponding ΔfHºliquid = -12.3 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
| ΔcH°liquid | -1334.1 | kcal/mol | Ccb | Hock and Knauel, 1951 | Corresponding ΔfHºliquid = -16.3 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| S°liquid | 60.100 | 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 |
|---|---|---|---|
| 51.969 | 298.15 | McCullough, Finke, et al., 1957 | T = 10 to 320 K.; DH |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Good and Lee, 1976
Good, W.D.; Lee, S.H.,
The enthalpies of formation of selected naphthalenes, diphenylmethanes, and bicyclic hydrocarbons,
J. Chem. Thermodyn., 1976, 8, 643-650. [all data]
Boyd, Sanwal, et al., 1971
Boyd, R.H.; Sanwal, S.N.; Shary-Tehrany, S.; McNally, D.,
The thermochemistry, thermodynamic functions, and molecular structures of some cyclic hydrocarbons,
J. Phys. Chem., 1971, 75, 1264-1271. [all data]
Pedley, Naylor, et al., 1986
Pedley, J.B.; Naylor, R.D.; Kirby, S.P.,
Thermochemical Data of Organic Compounds, Chapman and Hall, New York, 1986, 1-792. [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]
Dorofeeva O.V., 1986
Dorofeeva O.V.,
On calculation of thermodynamic properties of polycyclic aromatic hydrocarbons,
Thermochim. Acta, 1986, 102, 59-66. [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]
Boyd R.H., 1971
Boyd R.H.,
The thermochemistry, thermodynamic functions, and molecular structures of some cyclic hydrocarbons,
J. Phys. Chem., 1971, 75, 1264-1271. [all data]
Szekely, 1955
Szekely, A.,
Semiempirical method for calculating thermodynamic properties. The thermodynamic data of 1,2,3,4-tetrahydronaphthalene,
Acta Chim. Acad. Sci. Hung., 1955, 5, 317-339. [all data]
Vvedenskii A.A., 1957
Vvedenskii A.A.,
Reaction equilibrium of hydrocarbons. X. Heat capacity of naphthalene, tetrahydronaphthalene, and decahydronaphthalene,
Zh. Obshch. Khim., 1957, 27, 2052-2054. [all data]
Karo, McLaughlin, et al., 1953
Karo, W.; McLaughlin, R.L.; Hipsher, H.F.,
Dicyclic hydrocarbons. VI. 1,2,3,4-Tetrahydronaphthalene and 1-alkyl-1,2,3,4-tetrahydronaphthalenes,
J. Am. Chem. Soc., 1953, 75, 3233-3235. [all data]
Hock and Knauel, 1951
Hock, I.H.; Knauel, G.,
Autoxydation von kohlenwasserstoffen, XIV. Mitteil. Uber die energetische stellung organischer hydroperoxyde,
Chem. Ber., 1951, 84, 1-5. [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]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, References
- Symbols used in this document:
Cp,gas Constant pressure heat capacity of gas 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 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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