Indene
- Formula: C9H8
- Molecular weight: 116.1598
- IUPAC Standard InChI: InChI=1S/C9H8/c1-2-5-9-7-3-6-8(9)4-1/h1-6H,7H2
- IUPAC Standard InChIKey: YBYIRNPNPLQARY-UHFFFAOYSA-N
- CAS Registry Number: 95-13-6
- 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. - Other names: 1H-Indene
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Reaction thermochemistry data
Go To: Top, Mass spectrum (electron ionization), UV/Visible spectrum, 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:
B - John E. Bartmess
ALS - 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
+
=
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 1482. ± 10. | kJ/mol | TDEq | Meot-ner, Liebman, et al., 1988 | gas phase; anchored to 88MEO scale, not the "87 acidity scale". The Kiefer, Zhang, et al., 1997 BDE is for ortho.; B |
| ΔrH° | 1472. ± 8.8 | kJ/mol | G+TS | Taft and Bordwell, 1988 | gas phase; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 1451. ± 8.4 | kJ/mol | TDEq | Meot-ner, Liebman, et al., 1988 | gas phase; anchored to 88MEO scale, not the "87 acidity scale". The Kiefer, Zhang, et al., 1997 BDE is for ortho.; B |
| ΔrG° | 1442. ± 8.4 | kJ/mol | IMRE | Taft and Bordwell, 1988 | gas phase; B |
+
=
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -98.9 ± 1.4 | kJ/mol | Chyd | Hill, Morton, et al., 1980 | liquid phase; ALS |
| ΔrH° | -96. | kJ/mol | Eqk | Frye and Weitkamp, 1969 | gas phase; ALS |
| ΔrH° | -90.48 ± 0.59 | kJ/mol | Eqk | Naidus and Mueller, 1950 | gas phase; At 375-525 K; ALS |
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; ALS |
Mass spectrum (electron ionization)
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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: NIST Mass Spectrometry Data Center, William E. Wallace, director
Spectrum
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Additional Data
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Due to licensing restrictions, this spectrum cannot be downloaded.
| 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- 50 |
| NIST MS number | 228349 |
UV/Visible spectrum
Go To: Top, Reaction thermochemistry data, Mass spectrum (electron ionization), References, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data compiled by: Victor Talrose, Eugeny B. Stern, Antonina A. Goncharova, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina
Spectrum
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Additional Data
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| Source | Rambart-Lucas and Grumes, 1950 |
|---|---|
| Owner | INEP CP RAS, NIST OSRD Collection (C) 2007 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
| Origin | INSTITUTE OF ENERGY PROBLEMS OF CHEMICAL PHYSICS, RAS |
| Source reference | RAS UV No. 477 |
| Instrument | n.i.g. |
| Melting point | -1.8 |
| Boiling point | 182 |
References
Go To: Top, Reaction thermochemistry data, Mass spectrum (electron ionization), UV/Visible spectrum, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Meot-ner, Liebman, et al., 1988
Meot-ner, M.; Liebman, J.F.; Kafafi, S.A.,
Ionic Probes of Aromaticity in Annelated Rings,
J. Am. Chem. Soc., 1988, 110, 18, 5937, https://doi.org/10.1021/ja00226a001
. [all data]
Kiefer, Zhang, et al., 1997
Kiefer, J.H.; Zhang, Q.; Kern, R.D.; Yao, J.; Jursic, B.,
Pyrolysis of Aromatic Azines: Pyrazine, Pyrimidine, and Pyridine,
J. Phys. Chem. A, 1997, 101, 38, 7061, https://doi.org/10.1021/jp970211z
. [all data]
Taft and Bordwell, 1988
Taft, R.W.; Bordwell, F.G.,
Structural and Solvent Effects Evaluated from Acidities Measured in Dimethyl Sulfoxide and in the Gas Phase,
Acc. Chem. Res., 1988, 21, 12, 463, https://doi.org/10.1021/ar00156a005
. [all data]
Hill, Morton, et al., 1980
Hill, R.K.; Morton, G.H.; Rogers, D.W.; Choi, L.S.,
Rearrangement of 1,1'-spirobiindene and thermochemical evidence for its spiroconjugative destabilization,
J. Org. Chem., 1980, 45, 5163-5166. [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]
Naidus and Mueller, 1950
Naidus, E.S.; Mueller, M.B.,
Equilibrium studies on the hydrindene-indene-hydrogen system,
J. Am. Chem. Soc., 1950, 72, 1829-1831. [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]
Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G.,
Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]
Rambart-Lucas and Grumes, 1950
Rambart-Lucas, M.; Grumes, M.,
Sur la deformation des orbites electroniques du carbone et de l'azote dans les combinaisons heterocycliques,
Bull. Soc. Chim. Fr., 1950, 17, 317-322. [all data]
Notes
Go To: Top, Reaction thermochemistry data, Mass spectrum (electron ionization), UV/Visible spectrum, References
- Symbols used in this document:
ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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