Indane
- Formula: C9H10
- Molecular weight: 118.1757
- IUPAC Standard InChI: InChI=1S/C9H10/c1-2-5-9-7-3-6-8(9)4-1/h1-2,4-5H,3,6-7H2
- IUPAC Standard InChIKey: PQNFLJBBNBOBRQ-UHFFFAOYSA-N
- CAS Registry Number: 496-11-7
- Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
View 3d structure (requires JavaScript / HTML 5) - Other names: 1H-Indene, 2,3-dihydro-; Indan; Benzocyclopentane; Hydrindene; Indene, 2,3-dihydro-; 1,2-Hydrindene; 2,3-Dihydroindene; 2,3-Dihydro-1H-indene; Hydrindonaphthene; NSC 5292
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Gas 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:
DRB - Donald R. Burgess, Jr.
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°gas | 14.6 ± 0.50 | kcal/mol | Review | Roux, Temprado, et al., 2008 | There are sufficient high-quality literature values to make a good evaluation with a high degree of confidence. In general, the evaluated uncertainty limits are on the order of (0.5 to 2.5) kJ/mol.; DRB |
| ΔfH°gas | 14.5 ± 0.36 | kcal/mol | N/A | Good, 1971 | Value computed using ΔfHliquid° value of 11.7±1.5 kj/mol from Good, 1971 and ΔvapH° value of 49.03±0.2 kj/mol from missing citation.; DRB |
| ΔfH°gas | 14.3 ± 0.48 | kcal/mol | N/A | Stull, Sinke, et al., 1961 | Value computed using ΔfHliquid° value of 10.7±2 kj/mol from Stull, Sinke, et al., 1961 and ΔvapH° value of 49.03±0.2 kj/mol from missing citation.; DRB |
Constant pressure heat capacity of gas
| Cp,gas (cal/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 9.285 | 50. | Dorofeeva O.V., 1989 | GT |
| 12.05 | 100. | ||
| 15.59 | 150. | ||
| 20.16 | 200. | ||
| 28.279 | 273.15 | ||
| 31.25 ± 0.24 | 298.15 | ||
| 31.470 | 300. | ||
| 43.059 | 400. | ||
| 53.040 | 500. | ||
| 61.166 | 600. | ||
| 67.768 | 700. | ||
| 73.198 | 800. | ||
| 77.725 | 900. | ||
| 81.534 | 1000. | ||
| 84.766 | 1100. | ||
| 87.517 | 1200. | ||
| 89.873 | 1300. | ||
| 91.900 | 1400. | ||
| 93.647 | 1500. |
Constant pressure heat capacity of gas
| Cp,gas (cal/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 46.281 ± 0.093 | 435.65 | Hossenlopp I.A., 1981 | GT |
| 47.598 ± 0.093 | 448.15 | ||
| 50.005 ± 0.093 | 473.15 | ||
| 52.390 ± 0.093 | 498.15 | ||
| 54.582 ± 0.093 | 523.15 |
Reaction thermochemistry data
Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics data, 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: 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° | -23.63 ± 0.33 | kcal/mol | Chyd | Hill, Morton, et al., 1980 | liquid phase |
| ΔrH° | -23. | kcal/mol | Eqk | Frye and Weitkamp, 1969 | gas phase |
| ΔrH° | -21.63 ± 0.14 | kcal/mol | Eqk | Naidus and Mueller, 1950 | gas phase; At 375-525 K |
6 + 2
=
+
By formula: 6H2 + 2C9H10 = C9H16 + C9H16
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -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 +
=
By formula: 3H2 + C9H10 = C9H16
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -45.8 | kcal/mol | Eqk | Frye and Weitkamp, 1969 | gas phase |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, 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:
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 C9H10+ (ion structure unspecified)
Ionization energy determinations
| IE (eV) | Method | Reference | Comment |
|---|---|---|---|
| 8.6 ± 0.1 | EI | Koppel, Schwarz, et al., 1974 | LLK |
| 8.60 ± 0.01 | EI | Rakita, Hoffman, et al., 1973 | LLK |
| 8.52 | CTS | Pitt, 1970 | RDSH |
| 9.05 ± 0.05 | EI | Meier, Heiss, et al., 1968 | RDSH |
| 8.50 | PE | Santiago, Gandour, et al., 1978 | Vertical value; LLK |
| 8.46 ± 0.03 | PE | Heilbronner, Hoshi, et al., 1976 | Vertical value; LLK |
| 8.45 ± 0.02 | PE | Maier and Turner, 1973 | Vertical value; LLK |
| 8.46 | PE | Brogli, Giovannini, et al., 1973 | Vertical value; LLK |
Appearance energy determinations
| Ion | AE (eV) | Other Products | Method | Reference | Comment |
|---|---|---|---|---|---|
| C9H9+ | 12.1 ± 0.1 | H | EI | Koppel, Schwarz, et al., 1974 | LLK |
References
Go To: Top, Gas 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.
Roux, Temprado, et al., 2008
Roux, M.V.; Temprado, M.; Chickos, J.S.; Nagano, Y.,
Critically Evaluated Thermochemical Properties of Polycyclic Aromatic Hydrocarbons,
J. Phys. Chem. Ref. Data, 2008, 37, 4, 1855-1996. [all data]
Good, 1971
Good, W.D.,
The enthalpies of combustion and formation of indan and seven alkylindans,
J. Chem. Thermodyn., 1971, 3, 711-717. [all data]
Stull, Sinke, et al., 1961
Stull, D.R.; Sinke, G.C.; McDonald, R.A.; Hatton, W.E.; Hildenbrand, D.L.,
Thermodynamic properties of indane and indene,
Pure & Appl. Chem., 1961, 2, 315-322. [all data]
Dorofeeva O.V., 1989
Dorofeeva O.V.,
Thermodynamic Properties of Gaseous Polycyclic Aromatic Hydrocarbons Containing Five-Membered Rings. Institute for High Temperatures, USSR Academy of Sciences, Preprint No.1-263 (in Russian), Moscow, 1989. [all data]
Hossenlopp I.A., 1981
Hossenlopp I.A.,
Vapor heat capacities and enthalpies of vaporization of four aromatic and/or cycloalkane hydrocarbons,
J. Chem. Thermodyn., 1981, 13, 423-428. [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]
Koppel, Schwarz, et al., 1974
Koppel, C.; Schwarz, H.; Bohlmann, F.,
Elektronenstossinduzierte fragmentierung von acetylenverbindungen. VIII. Struktur der stabilen und instabilen ionen[C9H9]+ aus isomeren C9H10- kohlenwasserstoffen,
Org. Mass Spectrom., 1974, 8, 25. [all data]
Rakita, Hoffman, et al., 1973
Rakita, P.E.; Hoffman, M.K.; Andrews, M.N.; Bursey, M.M.,
σ-π Conjugation in group IVA compounds of indene and indane,
J. Organomet. Chem., 1973, 49, 213. [all data]
Pitt, 1970
Pitt, C.G.,
Hyperconjugation: An alternative to the concept of the pπ-dπ bond in Group IV chemistry,
J. Organomet. Chem., 1970, 23, 35. [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]
Santiago, Gandour, et al., 1978
Santiago, C.; Gandour, R.W.; Houk, K.N.; Nutakul, W.; Cravey, W.E.; Thummel, R.P.,
Photoelectron and ultraviolet spectra of small-ring fused aromatic molecules as probes of aromatic ring distortions,
J. Am. Chem. Soc., 1978, 100, 3730. [all data]
Heilbronner, Hoshi, et al., 1976
Heilbronner, E.; Hoshi, T.; von Rosenberg, J.L.; Hafner, K.,
Alkyl-induced, natural hypsochromic shifts of the 2A←2X and 2B←2X transitions of azulene and naphthalene radical cations,
Nouv. J. Chim., 1976, 1, 105. [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
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance energy Cp,gas Constant pressure heat capacity of gas ΔfH°gas Enthalpy of formation of gas at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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