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
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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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Gas phase thermochemistry data

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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
Δ_fH°_gas	30.0	kJ/mol	N/A	Good and Lee, 1976	Value computed using Δ_fH_liquid° value of -28.6±1.0 kj/mol from Good and Lee, 1976 and Δ_vapH° value of 58.6 kj/mol from Boyd, Sanwal, et al., 1971.; DRB
Δ_fH°_gas	26.0 ± 2.0	kJ/mol	Ccb	Boyd, Sanwal, et al., 1971	Reanalyzed by Pedley, Naylor, et al., 1986, Original value = 22.1 ± 3.4 kJ/mol; ALS

Constant pressure heat capacity of gas

C_p,gas (J/mol*K)	Temperature (K)	Reference	Comment
39.51	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/molK 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/molK 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
55.34	100.
75.22	150.
98.28	200.
136.97	273.15
150.9 ± 2.0	298.15
151.98	300.
206.65	400.
254.31	500.
293.63	600.
325.91	700.
352.66	800.
375.08	900.
394.00	1000.
410.07	1100.
423.77	1200.
435.51	1300.
445.60	1400.
454.31	1500.

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	-28.6 ± 1.0	kJ/mol	Ccb	Good and Lee, 1976	ALS
Δ_fH°_liquid	-32.6 ± 2.2	kJ/mol	Ccb	Boyd, Sanwal, et al., 1971	Reanalyzed by Pedley, Naylor, et al., 1986, Original value = -33.1 ± 2.1 kJ/mol; ALS
Quantity	Value	Units	Method	Reference	Comment
Δ_cH°_liquid	-5621.54 ± 0.88	kJ/mol	Ccb	Good and Lee, 1976	Corresponding Δ_fHº_liquid = -28.5 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Δ_cH°_liquid	-5617.5 ± 2.1	kJ/mol	Ccb	Boyd, Sanwal, et al., 1971	Corresponding Δ_fHº_liquid = -32.6 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Δ_cH°_liquid	-5598.6	kJ/mol	Ccb	Karo, McLaughlin, et al., 1953	Corrected from net heat of combustion; Corresponding Δ_fHº_liquid = -51.5 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Δ_cH°_liquid	-5581.9	kJ/mol	Ccb	Hock and Knauel, 1951	Corresponding Δ_fHº_liquid = -68.2 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity	Value	Units	Method	Reference	Comment
S°_liquid	251.46	J/mol*K	N/A	McCullough, Finke, et al., 1957	DH

Constant pressure heat capacity of liquid

C_p,liquid (J/mol*K)	Temperature (K)	Reference	Comment
217.44	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°	-125.	kJ/mol	Eqk	Frye and Weitkamp, 1969	gas phase
Δ_rH°	-120.5 ± 5.0	kJ/mol	Eqk	Wilson, Caflisch, et al., 1958	gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -133.9 ± 5.0 kJ/mol; At 400 K

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

By formula: H₂ + C₁₀H₁₀ = C₁₀H₁₂

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-100.83 ± 0.83	kJ/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°	-113.5 ± 0.4	kJ/mol	Chyd	Williams, 1942	liquid phase; solvent: Acetic acid; At 302 K

Gas phase ion energetics data

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Data evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias
L - Sharon G. Lias

Data compiled as indicated in comments:
MM - Michael M. Meot-Ner (Mautner)
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
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

View reactions leading to C₁₀H₁₂⁺ (ion structure unspecified)

Quantity	Value	Units	Method	Reference	Comment
IE (evaluated)	8.46 ± 0.02	eV	N/A	N/A	L
Quantity	Value	Units	Method	Reference	Comment
Proton affinity (review)	809.7	kJ/mol	N/A	Hunter and Lias, 1998	HL
Quantity	Value	Units	Method	Reference	Comment
Gas basicity	782.1	kJ/mol	N/A	Hunter and Lias, 1998	HL

Proton affinity at 298K

Proton affinity (kJ/mol)	Reference	Comment
800.8	Aue, Guidoni, et al., 2000	Experimental literature data re-evaluated by the authors using ab initio protonation entropies; MM

Gas basicity at 298K

Gas basicity (review) (kJ/mol)	Reference	Comment
774.0	Aue, Guidoni, et al., 2000	Experimental literature data re-evaluated by the authors using ab initio protonation entropies; MM

Ionization energy determinations

IE (eV)	Method	Reference	Comment
8.44	EI	Dass and Gross, 1985	LBLHLM
8.48 ± 0.05	EQ	Mautner(Meot-Ner), 1980	LLK
8.47	CTS	Pitt, 1970	RDSH
8.73	EI	Loudon, Maccoll, et al., 1970	RDSH
9.14 ± 0.05	EI	Meier, Heiss, et al., 1968	RDSH
8.45 ± 0.02	PE	Maier and Turner, 1973	Vertical value; LLK
8.44	PE	Brogli, Giovannini, et al., 1973	Vertical value; LLK

Appearance energy determinations

Ion	AE (eV)	Other Products	Method	Reference	Comment
C₈H₈⁺	11.31	?	EI	Loudon, Maccoll, et al., 1970	RDSH

References

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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]

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]

Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G., Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update, J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018 . [all data]

Aue, Guidoni, et al., 2000
Aue, D.H.; Guidoni, M.; Betowski, L.D., Ab initio calculated gas-phase basicities of polynuclear aromatic hydrocarbons, Int. J. Mass Spectrom., 2000, 201, 283. [all data]

Dass and Gross, 1985
Dass, C.; Gross, M.L., The question of cyclic versus acyclic ions: The structure of [C₆H₁₀]⁺ gas phase ions, Org. Mass Spectrom., 1985, 20, 34. [all data]

Mautner(Meot-Ner), 1980
Mautner(Meot-Ner), M., Ion thermochemistry of low volatility compounds in the gas phase. 3. Polycyclic aromatics: Ionization energies, proton, and hydrogen affinities. Extrapolations to graphite, J. Phys. Chem., 1980, 84, 2716. [all data]

Pitt, 1970
Pitt, C.G., Hyperconjugation: An alternative to the concept of the p_π-d_π bond in Group IV chemistry, J. Organomet. Chem., 1970, 23, 35. [all data]

Loudon, Maccoll, et al., 1970
Loudon, A.G.; Maccoll, A.; Wong, S.K., Comparison between unimolecular gas phase pyrolysis and electron impact fragmentation. Part I. The mass spectra of tetralin and some related heterocycles, J. Chem. Soc. B, 1970, 1727. [all data]

Meier, Heiss, et al., 1968
Meier, H.; Heiss, J.; Suhr, H.; Muller, E., Energetische Untersuchungen zum Mills-Nixon-Effekt. Ionisierungsenergien von Benzolmolekulen mit ankondensierten gesattigten Ringen, Tetrahedron, 1968, 24, 2307. [all data]

Maier and Turner, 1973
Maier, J.P.; Turner, D.W., Steric inhibition of resonance studied by molecular photoelectron spectroscopy. Part 2. Phenylethylenes, J. Chem. Soc. Faraday Trans. 2, 1973, 69, 196. [all data]

Brogli, Giovannini, et al., 1973
Brogli, F.; Giovannini, E.; Heilbronner, E.; Schurter, R., Die photoelektronen spektren der benzocycloalkene, Chem. Ber., 1973, 106, 961. [all data]

Notes

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Symbols used in this document:

AE	Appearance energy
C_p,gas	Constant pressure heat capacity of gas
C_p,liquid	Constant pressure heat capacity of liquid
IE (evaluated)	Recommended ionization energy
S°_liquid	Entropy of liquid at standard conditions
Δ_cH°_liquid	Enthalpy of combustion of liquid at standard conditions
Δ_fH°_gas	Enthalpy of formation of gas 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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