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
The 3d structure may be viewed using Java or Javascript.
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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Other data available:
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- Gas Phase Kinetics Database
- NIST Polycyclic Aromatic Hydrocarbon Structure Index
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Gas phase thermochemistry data

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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
Δ_fH°_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
Δ_fH°_gas	14.5 ± 0.36	kcal/mol	N/A	Good, 1971	Value computed using Δ_fH_liquid° value of 11.7±1.5 kj/mol from Good, 1971 and Δ_vapH° value of 49.03±0.2 kj/mol from missing citation.; DRB
Δ_fH°_gas	14.3 ± 0.48	kcal/mol	N/A	Stull, Sinke, et al., 1961	Value computed using Δ_fH_liquid° value of 10.7±2 kj/mol from Stull, Sinke, et al., 1961 and Δ_vapH° value of 49.03±0.2 kj/mol from missing citation.; DRB

Constant pressure heat capacity of gas

C_p,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

C_p,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

Condensed phase thermochemistry data

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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
Δ_fH°_liquid	2.80 ± 0.43	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
Δ_fH°_liquid	2.80 ± 0.35	kcal/mol	Ccb	Good, 1971	ALS
Δ_fH°_liquid	2.56 ± 0.47	kcal/mol	Ccb	Stull, Sinke, et al., 1961	see Stull, Sinke, et al., 1959; ALS
Quantity	Value	Units	Method	Reference	Comment
Δ_cH°_liquid	-1190.84 ± 0.33	kcal/mol	Ccb	Good, 1971	Corresponding Δ_fHº_liquid = 2.80 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Δ_cH°_liquid	-1190.63 ± 0.47	kcal/mol	Ccb	Stull, Sinke, et al., 1961	see Stull, Sinke, et al., 1959; Corresponding Δ_fHº_liquid = 2.59 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity	Value	Units	Method	Reference	Comment
S°_liquid	56.011	cal/mol*K	N/A	Stull, Sinke, et al., 1961	DH
S°_liquid	56.009	cal/mol*K	N/A	Stull, Sinke, et al., 1959, 2	DH

Constant pressure heat capacity of liquid

C_p,liquid (cal/mol*K)	Temperature (K)	Reference	Comment
45.471	298.15	Stull, Sinke, et al., 1961	T = 15 to 320 K. Premelting occurs at 170 K to melting.; DH
45.471	298.15	Stull, Sinke, et al., 1959, 2	T = 15 to 320 K.; DH

Phase change data

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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
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
T_boil	450. ± 2.	K	AVG	N/A	Average of 9 values; Individual data points
Quantity	Value	Units	Method	Reference	Comment
T_fus	221.46	K	N/A	Boord, Perilstein, et al., 1944	Uncertainty assigned by TRC = 0.4 K; TRC
Quantity	Value	Units	Method	Reference	Comment
T_triple	221.77	K	N/A	Stull, Sinke, et al., 1959, 3	Uncertainty assigned by TRC = 0.02 K; TRC
Quantity	Value	Units	Method	Reference	Comment
T_c	684.9 ± 0.5	K	N/A	Tsonopoulos and Ambrose, 1995
T_c	684.9	K	N/A	Majer and Svoboda, 1985
T_c	684.9	K	N/A	Ambrose, Broderick, et al., 1974	Uncertainty assigned by TRC = 0.4 K; TRC
Quantity	Value	Units	Method	Reference	Comment
P_c	39.0 ± 0.4	atm	N/A	Tsonopoulos and Ambrose, 1995
P_c	38.98	atm	N/A	Ambrose, Broderick, et al., 1974	Uncertainty assigned by TRC = 0.30 atm; TRC
Quantity	Value	Units	Method	Reference	Comment
Δ_vapH°	11.7	kcal/mol	N/A	Majer and Svoboda, 1985
Δ_vapH°	11.8 ± 0.24	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
Δ_vapH°	11.7	kcal/mol	C	Hossenlopp and Scott, 1981	AC
Δ_vapH°	11.72 ± 0.048	kcal/mol	V	Osborn and Scott, 1978	ALS

Enthalpy of vaporization

Δ_vapH (kcal/mol)	Temperature (K)	Method	Reference	Comment
9.472	451.	N/A	Majer and Svoboda, 1985
10.5	389.	A	Stephenson and Malanowski, 1987	Based on data from 374. to 466. K.; AC
10.8	370.	N/A	Ambrose and Sprake, 1976	Based on data from 355. to 482. K.; AC

Enthalpy of vaporization

Δ_vapH = A exp(-βT_r) (1 − T_r)^β
Δ_vapH = Enthalpy of vaporization (at saturation pressure) (kcal/mol)
T_r = reduced temperature (T / T_c)

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Temperature (K)	A (kcal/mol)	β	T_c (K)	Reference	Comment
382. to 451.	15.6	0.2866	684.9	Majer and Svoboda, 1985

Enthalpy of fusion

Δ_fusH (kcal/mol)	Temperature (K)	Reference	Comment
2.055	221.77	Stull, Sinke, et al., 1959, 2	DH
2.1	221.8	Domalski and Hearing, 1996	AC

Entropy of fusion

Δ_fusS (cal/mol*K)	Temperature (K)	Reference	Comment
9.266	221.77	Stull, Sinke, et al., 1959, 2	DH

Enthalpy of phase transition

ΔH_trs (kcal/mol)	Temperature (K)	Initial Phase	Final Phase	Reference	Comment
0.187	73.82	crystaline, II	crystaline, I	Stull, Sinke, et al., 1961	DH
2.055	221.77	crystaline, I	liquid	Stull, Sinke, et al., 1961	DH

Entropy of phase transition

ΔS_trs (cal/mol*K)	Temperature (K)	Initial Phase	Final Phase	Reference	Comment
2.526	73.82	crystaline, II	crystaline, I	Stull, Sinke, et al., 1961	DH
9.266	221.77	crystaline, I	liquid	Stull, Sinke, et al., 1961	DH

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:

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

+ = Indane

By formula: H₂ + C₉H₈ = C₉H₁₀

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-23.63 ± 0.33	kcal/mol	Chyd	Hill, Morton, et al., 1980	liquid phase
Δ_rH°	-23.	kcal/mol	Eqk	Frye and Weitkamp, 1969	gas phase
Δ_rH°	-21.63 ± 0.14	kcal/mol	Eqk	Naidus and Mueller, 1950	gas phase; At 375-525 K

6 + 2 Indane = +

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 + Indane =

By formula: 3H₂ + C₉H₁₀ = C₉H₁₆

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

Gas phase ion energetics data

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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, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Notes

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]

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]

Boord, Perilstein, et al., 1944
Boord, C.E.; Perilstein, W.L.; Greenlee, K.W., , Am. Pet. Inst. Hydrocarbon Res. Proj., Sixth Annu. Ref., Ohio State Univ., Aug. 31, 1944. [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]

Tsonopoulos and Ambrose, 1995
Tsonopoulos, C.; Ambrose, D., Vapor-Liquid Critical Properties of Elements and Compounds. 3. Aromatic Hydrocarbons, J. Chem. Eng. Data, 1995, 40, 547-558. [all data]

Majer and Svoboda, 1985
Majer, V.; Svoboda, V., Enthalpies of Vaporization of Organic Compounds: A Critical Review and Data Compilation, Blackwell Scientific Publications, Oxford, 1985, 300. [all data]

Ambrose, Broderick, et al., 1974
Ambrose, D.; Broderick, B.E.; Townsend, R., The Critical Temperatures and Pressures of Thirty Organic Compounds, J. Appl. Chem. Biotechnol., 1974, 24, 359. [all data]

Hossenlopp and Scott, 1981
Hossenlopp, I.A.; Scott, D.W., Vapor heat capacities and enthalpies of vaporization of four aromatic and/or cycloalkane hydrocarbons, J. Chem. Thermodyn., 1981, 13, 423-428. [all data]

Osborn and Scott, 1978
Osborn, A.G.; Scott, D.W., J. Chem. Thermodyn., 1978, 10, 619. [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]

Ambrose and Sprake, 1976
Ambrose, D.; Sprake, C.H.S., The vapour pressure of indane, The Journal of Chemical Thermodynamics, 1976, 8, 6, 601-602, https://doi.org/10.1016/0021-9614(76)90033-1 . [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]

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 p_π-d_π 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

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Symbols used in this document:

AE	Appearance energy
C_p,gas	Constant pressure heat capacity of gas
C_p,liquid	Constant pressure heat capacity of liquid
P_c	Critical pressure
S°_liquid	Entropy of liquid at standard conditions
T_boil	Boiling point
T_c	Critical temperature
T_fus	Fusion (melting) point
T_triple	Triple point temperature
ΔH_trs	Enthalpy of phase transition
ΔS_trs	Entropy of phase transition
Δ_cH°_liquid	Enthalpy of combustion of liquid at standard conditions
Δ_fH°_gas	Enthalpy of formation of gas at standard conditions
Δ_fH°_liquid	Enthalpy of formation of liquid at standard conditions
Δ_fusH	Enthalpy of fusion
Δ_fusS	Entropy of fusion
Δ_rH°	Enthalpy of reaction at standard conditions
Δ_vapH	Enthalpy of vaporization
Δ_vapH°	Enthalpy of vaporization at standard conditions

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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