1H-Indene, octahydro-, cis-

Formula: C₉H₁₆
Molecular weight: 124.2233
IUPAC Standard InChI: InChI=1S/C9H16/c1-2-5-9-7-3-6-8(9)4-1/h8-9H,1-7H2/t8-,9+
IUPAC Standard InChIKey: BNRNAKTVFSZAFA-DTORHVGOSA-N
CAS Registry Number: 4551-51-3
Chemical structure:
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Stereoisomers:
Other names: Indan, hexahydro-, cis-; cis-Bicyclo[4.3.0]Nonane; cis-Hexahydroindan; cis-Hydrindan; cis-Perhydroindene; cis-Octahydro-1H-indene; Octahydro-1H-indene, cis; cis-Hydrindane; Indene, octahydro-, cis-; cis-hexahydrindan
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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	-41.41 ± 0.36	kcal/mol	Ccb	Browne and Rossini, 1960	ALS
Quantity	Value	Units	Method	Reference	Comment
Δ_cH°_liquid	-1351.60 ± 0.36	kcal/mol	Ccb	Browne and Rossini, 1960	Corresponding Δ_fHº_liquid = -41.38 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Δ_cH°_liquid	-1349.6 ± 1.4	kcal/mol	Ccb	Huckel, Kamenz, et al., 1937	Reanalyzed by Cox and Pilcher, 1970, Original value = -1348. ± 4. kcal/mol; Corresponding Δ_fHº_liquid = -43.38 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity	Value	Units	Method	Reference	Comment
S°_liquid	63.449	cal/mol*K	N/A	Finke, McCullough, et al., 1972	DH

Constant pressure heat capacity of liquid

C_p,liquid (cal/mol*K)	Temperature (K)	Reference	Comment
51.190	298.15	Finke, McCullough, et al., 1972	T = 10 to 370 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

1H-Indene, octahydro-, cis- =

By formula: C₉H₁₆ = C₉H₁₆

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-0.740	kcal/mol	Eqk	Finke, McCullough, et al., 1972	liquid phase
Δ_rH°	-0.58 ± 0.05	kcal/mol	Eqk	Blanchard and Schleyer, 1963	liquid phase; Heat of isomerization
Δ_rH°	-1.07 ± 0.09	kcal/mol	Eqk	Allinger and Coke, 1960	liquid phase

8 + 2 = + 1H-Indene, octahydro-, cis-

By formula: 8H₂ + 2C₉H₈ = C₉H₁₆ + C₉H₁₆

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-139.9 ± 1.0	kcal/mol	Chyd	Dolliver, Gresham, et al., 1937	gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -140.4 ± 1.0 kcal/mol; At 355 °K

6 + 2 = + 1H-Indene, octahydro-, cis-

By formula: 6H₂ + 2C₉H₁₀ = C₉H₁₆ + C₉H₁₆

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-90.12 ± 0.50	kcal/mol	Chyd	Dolliver, Gresham, et al., 1937	gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -91.6 ± 0.5 kcal/mol; At 355 °K

3 + = 1H-Indene, octahydro-, cis-

By formula: 3H₂ + C₉H₁₀ = C₉H₁₆

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-45.8	kcal/mol	Eqk	Frye and Weitkamp, 1969	gas phase

= 1H-Indene, octahydro-, cis-

By formula: C₉H₁₆ = C₉H₁₆

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	1.065	kcal/mol	Eqk	Finke, McCullough, et al., 1972	gas phase

Mass spectrum (electron ionization)

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Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Spectrum

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Additional Data

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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-3544
NIST MS number	229756

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References

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Browne and Rossini, 1960
Browne, C.C.; Rossini, F.D., Heats of combustion, formation, and isomerization of the cis and trans isomers of hexahydroindan, J. Phys. Chem., 1960, 64, 927-931. [all data]

Huckel, Kamenz, et al., 1937
Huckel, W.; Kamenz, E.; Gross, A.; Tappe, W., Zur kenntnis der waldenschen umkehrung, Ann. Chim., 1937, 533, 1-45. [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]

Finke, McCullough, et al., 1972
Finke, H.L.; McCullough, J.P.; Messerly, J.F.; Osborn, A.; Douslin, D.R., cis- and trans-Hexahydroindan. Chemical thermodynamic properties and isomerization equilibrium, J. Chem. Thermodyn., 1972, 4, 477-494. [all data]

Blanchard and Schleyer, 1963
Blanchard, K.R.; Schleyer, P., Quantitative study of the interconversion of hydrindane isomers by aluminum bromide, J. Org. Chem., 1963, 28, 247-248. [all data]

Allinger and Coke, 1960
Allinger, N.L.; Coke, J.L., The relative stabilities of cis and trans isomers. VII. The hydrindanes, J. Am. Chem. Soc., 1960, 82, 2553-2556. [all data]

Dolliver, Gresham, et al., 1937
Dolliver, M.a.; Gresham, T.L.; Kistiakowsky, G.B.; Vaughan, W.E., Heats of organic reactions. V. Heats of hydrogenation of various hydrocarbons, J. Am. Chem. Soc., 1937, 59, 831-841. [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]

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
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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