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:
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: 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 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 | -173.3 ± 1.5 | kJ/mol | Ccb | Browne and Rossini, 1960 | ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°liquid | -5655.1 ± 1.5 | kJ/mol | Ccb | Browne and Rossini, 1960 | Corresponding ΔfHºliquid = -173.1 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
| ΔcH°liquid | -5646.7 ± 5.9 | kJ/mol | Ccb | Huckel, Kamenz, et al., 1937 | Reanalyzed by Cox and Pilcher, 1970, Original value = -5640. ± 20. kJ/mol; Corresponding ΔfHºliquid = -181.5 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| S°liquid | 265.47 | J/mol*K | N/A | Finke, McCullough, et al., 1972 | DH |
Constant pressure heat capacity of liquid
| Cp,liquid (J/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 214.18 | 298.15 | Finke, McCullough, et al., 1972 | T = 10 to 370 K.; DH |
Reaction 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
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
=
By formula: C9H16 = C9H16
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -3.10 | kJ/mol | Eqk | Finke, McCullough, et al., 1972 | liquid phase |
| ΔrH° | -2.4 ± 0.2 | kJ/mol | Eqk | Blanchard and Schleyer, 1963 | liquid phase; Heat of isomerization |
| ΔrH° | -4.5 ± 0.4 | kJ/mol | Eqk | Allinger and Coke, 1960 | liquid phase |
8 + 2
=
+
By formula: 8H2 + 2C9H8 = C9H16 + C9H16
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -585.2 ± 4.2 | kJ/mol | Chyd | Dolliver, Gresham, et al., 1937 | gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -587.4 ± 4.2 kJ/mol; At 355 °K |
6 + 2
=
+
By formula: 6H2 + 2C9H10 = C9H16 + C9H16
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -377.1 ± 2.1 | kJ/mol | Chyd | Dolliver, Gresham, et al., 1937 | gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -383. ± 2. kJ/mol; At 355 °K |
3 +
=
By formula: 3H2 + C9H10 = C9H16
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -192. | kJ/mol | Eqk | Frye and Weitkamp, 1969 | gas phase |
=
By formula: C9H16 = C9H16
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 4.456 | kJ/mol | Eqk | Finke, McCullough, et al., 1972 | gas phase |
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 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
View reactions leading to C9H16+ (ion structure unspecified)
Ionization energy determinations
| IE (eV) | Method | Reference | Comment |
|---|---|---|---|
| 9.46 ± 0.06 | PI | Mikaya and Zaikin, 1980 | LLK |
| 9.497 ± 0.003 | EI | Mikaya and Zaikin, 1980 | LLK |
| 10.13 ± 0.03 | EI | Natalis, 1963 | RDSH |
Appearance energy determinations
| Ion | AE (eV) | Other Products | Method | Reference | Comment |
|---|---|---|---|---|---|
| C5H7+ | 12.21 ± 0.05 | C2H5+C2H4 | EI | Natalis, 1963 | RDSH |
| C6H9+ | 11.99 ± 0.05 | ? | EI | Natalis, 1963 | RDSH |
| C6H10+ | 10.79 ± 0.03 | C3H6 | EI | Natalis, 1963 | RDSH |
| C7H11+ | 11.71 ± 0.05 | C2H5 | EI | Natalis, 1963 | RDSH |
| C7H12+ | 10.96 ± 0.03 | C2H4 | EI | Natalis, 1963 | RDSH |
References
Go To: Top, Condensed phase thermochemistry data, Reaction 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.
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]
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]
Natalis, 1963
Natalis, P.,
Etude du comportement d'isomeres geometriques sous l'impact electronique. II. Les cis et trans hexahydroindanes,
Bull. Soc. Chim. Belges, 1963, 72, 374. [all data]
Notes
Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance energy 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°liquid Enthalpy of formation of liquid at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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