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:
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Isotopologues:
- 1,2,3,4-Tetrahydronaphthalene-d12
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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Condensed phase thermochemistry data

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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
Δ_fH°_liquid	-6.83 ± 0.25	kcal/mol	Ccb	Good and Lee, 1976	ALS
Δ_fH°_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
Δ_cH°_liquid	-1343.58 ± 0.21	kcal/mol	Ccb	Good and Lee, 1976	Corresponding Δ_fHº_liquid = -6.82 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Δ_cH°_liquid	-1342.61 ± 0.51	kcal/mol	Ccb	Boyd, Sanwal, et al., 1971	Corresponding Δ_fHº_liquid = -7.79 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Δ_cH°_liquid	-1338.1	kcal/mol	Ccb	Karo, McLaughlin, et al., 1953	Corrected from net heat of combustion; Corresponding Δ_fHº_liquid = -12.3 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Δ_cH°_liquid	-1334.1	kcal/mol	Ccb	Hock and Knauel, 1951	Corresponding Δ_fHº_liquid = -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

C_p,liquid (cal/mol*K)	Temperature (K)	Reference	Comment
51.969	298.15	McCullough, Finke, et al., 1957	T = 10 to 320 K.; DH

Reaction thermochemistry data

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Data compiled by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. A general reaction search form is also available. Future versions of this site may rely on reaction search pages in place of the enumerated reaction displays seen below.

Individual Reactions

2 + = Naphthalene, 1,2,3,4-tetrahydro-

By formula: 2H₂ + C₁₀H₈ = C₁₀H₁₂

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-29.8	kcal/mol	Eqk	Frye and Weitkamp, 1969	gas phase
Δ_rH°	-28.8 ± 1.2	kcal/mol	Eqk	Wilson, Caflisch, et al., 1958	gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -32.0 ± 1.2 kcal/mol; At 400 K

+ = Naphthalene, 1,2,3,4-tetrahydro-

By formula: H₂ + C₁₀H₁₀ = C₁₀H₁₂

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-24.10 ± 0.20	kcal/mol	Chyd	Williams, 1942	liquid phase; solvent: Acetic acid; At 302 K

+ = Naphthalene, 1,2,3,4-tetrahydro-

By formula: H₂ + C₁₀H₁₀ = C₁₀H₁₂

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-27.1 ± 0.1	kcal/mol	Chyd	Williams, 1942	liquid phase; solvent: Acetic acid; At 302 K

Henry's Law data

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Data compiled by: Rolf Sander

Henry's Law constant (water solution)

k_H(T) = k°_H exp(d(ln(k_H))/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(k_H))/d(1/T) = Temperature dependence constant (K)

k°_H (mol/(kg*bar))	d(ln(k_H))/d(1/T) (K)	Method	Reference
0.52	5400.	X	N/A

References

Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, Henry's Law data, Notes

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]

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]

Frye and Weitkamp, 1969
Frye, C.G.; Weitkamp, A.W., Equilibrium hydrogenations of multi-ring aromatics, J. Chem. Eng. Data, 1969, 14, 372-376. [all data]

Wilson, Caflisch, et al., 1958
Wilson, T.P.; Caflisch, E.G.; Hurley, G.F., The naphthalene-tetralin-hydrogen equilibrium at elevated temperature and pressure, J. Phys. Chem., 1958, 62, 1059. [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]

Williams, 1942
Williams, R.B., Heats of catalytic hydrogenation in solution. I. Apparatus, technique, and the heats of hydrogenation of certain pairs of stereoisomers, J. Am. Chem. Soc., 1942, 64, 1395-1404. [all data]

Notes

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Symbols used in this document:

C_p,liquid	Constant pressure heat capacity of liquid
S°_liquid	Entropy of liquid at standard conditions
d(ln(k_H))/d(1/T)	Temperature dependence parameter for Henry's Law constant
k°_H	Henry's Law constant at 298.15K
Δ_cH°_liquid	Enthalpy of combustion of liquid at standard conditions
Δ_fH°_liquid	Enthalpy of formation of liquid at standard conditions
Δ_rH°	Enthalpy of reaction at standard conditions

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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