Indene
- Formula: C9H8
- Molecular weight: 116.1598
- 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
View 3d structure (requires JavaScript / HTML 5) - Other names: 1H-Indene
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Condensed phase thermochemistry data
Go To: Top, Phase change 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 as indicated in comments:
DRB - Donald R. Burgess, Jr.
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 | 110.6 ± 1.8 | kJ/mol | Review | Roux, Temprado, et al., 2008 | There are sufficient literature values to make a qualified recommendation where the suggested value is in good agreement with values predicted using thermochemical cycles or from reliable estimates. In general, the evaluated uncertainty limits are on the order of (2 to 4) kJ/mol.; DRB |
ΔfH°liquid | 110. ± 1. | kJ/mol | Ccb | Stull, Sinke, et al., 1961 | see Stull, Sinke, et al., 1959; ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -4795.5 ± 1.3 | kJ/mol | Ccb | Stull, Sinke, et al., 1961 | see Stull, Sinke, et al., 1959; Corresponding ΔfHºliquid = 110.6 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°liquid | 214.18 | J/mol*K | N/A | Stull, Sinke, et al., 1961 | DH |
S°liquid | 215.35 | J/mol*K | N/A | Stull, Sinke, et al., 1959, 2 | DH |
Constant pressure heat capacity of liquid
Cp,liquid (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
186.94 | 298.15 | Stull, Sinke, et al., 1961 | T = 15 to 320 K.; DH |
186.94 | 298.15 | Stull, Sinke, et al., 1959, 2 | T = 15 to 320 K.; DH |
Phase change data
Go To: Top, Condensed 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 as indicated in comments:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
DRB - Donald R. Burgess, Jr.
AC - William E. Acree, Jr., James S. Chickos
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 454. ± 4. | K | AVG | N/A | Average of 11 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 271.4 | K | N/A | Kravchenko and Pastukhova, 1953 | Uncertainty assigned by TRC = 0.5 K; TRC |
Tfus | 270.48 | K | N/A | Anonymous, 1943 | Uncertainty assigned by TRC = 0.3 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 271.70 | K | N/A | Stull, Sinke, et al., 1959, 3 | Uncertainty assigned by TRC = 0.02 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 50.6 ± 1.5 | kJ/mol | Review | Roux, Temprado, et al., 2008 | There are sufficient literature values to make a qualified recommendation where the suggested value is in good agreement with values predicted using thermochemical cycles or from reliable estimates. In general, the evaluated uncertainty limits are on the order of (2 to 4) kJ/mol.; DRB |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
45.3 | 384. | A | Stephenson and Malanowski, 1987 | Based on data from 369. to 457. K.; AC |
43.6 | 304. | A | Stephenson and Malanowski, 1987 | Based on data from 289. to 455. K. See also Stull, 1947.; AC |
43.9 | 392. | N/A | Burchfield, 1942 | Based on data from 329. to 454. K.; AC |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (bar)
T = temperature (K)
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Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
289.6 to 454.8 | 5.33514 | 2511.452 | 16.524 | Stull, 1947 | Coefficents calculated by NIST from author's data. |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
10.201 | 271.70 | Stull, Sinke, et al., 1961 | DH |
10.201 | 271.70 | Stull, Sinke, et al., 1959, 2 | DH |
10.2 | 271.7 | Domalski and Hearing, 1996 | AC |
Entropy of fusion
ΔfusS (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
37.55 | 271.70 | Stull, Sinke, et al., 1959, 2 | DH |
Gas phase ion energetics data
Go To: Top, Condensed phase thermochemistry data, Phase change data, References, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias
L - Sharon G. Lias
Data compiled as indicated in comments:
B - John E. Bartmess
MM - Michael M. Meot-Ner (Mautner)
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 C9H8+ (ion structure unspecified)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
IE (evaluated) | 8.14 ± 0.01 | eV | N/A | N/A | L |
Quantity | Value | Units | Method | Reference | Comment |
Proton affinity (review) | 848.8 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 819.6 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Electron affinity determinations
EA (eV) | Method | Reference | Comment |
---|---|---|---|
<0.173 ± 0.026 | ECD | Wojnarovits and Foldiak, 1981 | EA is an upper limit: Chen and Wentworth, 1989; G3MP2B3 calculations indicate an EA of ca. -0.6 eV, unbound anion.; B |
Proton affinity at 298K
Proton affinity (kJ/mol) | Reference | Comment |
---|---|---|
848.5 | 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 |
---|---|---|
819.2 | 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 |
---|---|---|---|
8.33 ± 0.01 | EI | Rakita, Hoffman, et al., 1973 | LLK |
8.14 ± 0.01 | PE | Dewar, Haselbach, et al., 1970 | RDSH |
8.62 | EI | Occolowitz and White, 1968 | RDSH |
8.13 ± 0.05 | PE | Eland and Danby, 1968 | RDSH |
8.15 ± 0.015 | PE | Gusten, Klasinc, et al., 1976 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C9H7+ | 12.62 ± 0.05 | H | EI | Schwarz and Bohlmann, 1973 | LLK |
C9H7+ | 12.53 | H | EI | Occolowitz and White, 1968 | RDSH |
De-protonation 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 |
References
Go To: Top, Condensed phase thermochemistry data, Phase change 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]
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]
Stull, Sinke, et al., 1959
Stull, D.R.; Sinke, G.C.; McDonald, R.A.; Hatton, W.E.; Hildenbrand, D.L.,
Thermodynamic properties of indane and indene,
Symposium uber Thermodynamik, 1959, 1-9. [all data]
Stull, Sinke, et al., 1959, 2
Stull, D.R.; Sinke, G.C.; McDonald, R.A.; Hatton, W.E.; Hildenbrand, D.L.,
Thermodynamic properties of indane and indene, Symp. Thermodynam. Fritens-Wattens,
Tirol Austria, 1959, No. 48, 9p. [all data]
Kravchenko and Pastukhova, 1953
Kravchenko, V.M.; Pastukhova, I.S.,
Ternary systems of indene+isoquinoline+naphthalene and naphthalene + isoquinoline+benzene,
Zh. Fiz. Khim., 1953, 27, 822. [all data]
Anonymous, 1943
Anonymous, R.,
, Sunbury Rep. No. 2176, Anglo-Iranian Oil Co., 1943. [all data]
Stull, Sinke, et al., 1959, 3
Stull, D.R.; Sinke, G.C.; McDonald, R.A.; Hatton, W.E.; Hildenbrand, D.L.,
Thermodynamic properties of indane and indene
in Symp. Thermodyn. Fritens-Wattens, Tirol, Austria, 1959. [all data]
Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw,
Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2
. [all data]
Stull, 1947
Stull, Daniel R.,
Vapor Pressure of Pure Substances. Organic and Inorganic Compounds,
Ind. Eng. Chem., 1947, 39, 4, 517-540, https://doi.org/10.1021/ie50448a022
. [all data]
Burchfield, 1942
Burchfield, P.E.,
Vapor Pressures of Indene, Styrene and Dicyclopentadiene,
J. Am. Chem. Soc., 1942, 64, 10, 2501-2501, https://doi.org/10.1021/ja01262a504
. [all data]
Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D.,
Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III,
J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985
. [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]
Wojnarovits and Foldiak, 1981
Wojnarovits, L.; Foldiak, G.,
Electron capture detection of aromatic hydrocarbons,
J. Chromatogr. Sci., 1981, 206, 511. [all data]
Chen and Wentworth, 1989
Chen, E.C.M.; Wentworth, W.E.,
Experimental Determination of Electron Affinities of Organic Molecules,
Mol. Cryst. Liq. Cryst., 1989, 171, 271. [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]
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]
Dewar, Haselbach, et al., 1970
Dewar, M.J.S.; Haselbach, E.; Worley, S.D.,
Calculated and observed ionization potentials of unsaturated polycyclic hydrocarbons; calculated heats of formation by several semiempirical s.c.f. m.o. methods,
Proc. Roy. Soc. (London), 1970, A315, 431. [all data]
Occolowitz and White, 1968
Occolowitz, J.L.; White, G.L.,
Energetic considerations in the assignment of some fragment ion structures,
Australian J. Chem., 1968, 21, 997. [all data]
Eland and Danby, 1968
Eland, J.H.D.; Danby, C.J.,
Inner ionization potentials of aromatic compounds,
Z. Naturforsch., 1968, 23a, 355. [all data]
Gusten, Klasinc, et al., 1976
Gusten, H.; Klasinc, L.; Ruscic, B.,
Photoelectron spectroscopy of J. Heterocycl. Chem.. Indene analogs,
Z. Naturforsch. A:, 1976, 31, 1051. [all data]
Schwarz and Bohlmann, 1973
Schwarz, H.; Bohlmann, F.,
Elektronenstossinduzierte fragmentierung von acetylenverbindungen. VI. Struktur und bildungsenthalpie der ionen [C11H9]+ und [C9H7]+,
Org. Mass Spectrom., 1973, 7, 395. [all data]
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]
Notes
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance energy Cp,liquid Constant pressure heat capacity of liquid EA Electron affinity IE (evaluated) Recommended ionization energy S°liquid Entropy of liquid at standard conditions Tboil Boiling point Tfus Fusion (melting) point Ttriple Triple point temperature ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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