Fluorene
- Formula: C13H10
- Molecular weight: 166.2185
- IUPAC Standard InChIKey: NIHNNTQXNPWCJQ-UHFFFAOYSA-N
- CAS Registry Number: 86-73-7
- 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: 9H-Fluorene; o-Biphenylenemethane; Diphenylenemethane; Methane, diphenylene-; 2,2'-Methylenebiphenyl; 2,3-Benzindene; o-Biphenylmethane
- Permanent link for this species. Use this link for bookmarking this species for future reference.
- Information on this page:
- Other data available:
- Data at other public NIST sites:
- Options:
Data at NIST subscription sites:
NIST subscription sites provide data under the NIST Standard Reference Data Program, but require an annual fee to access. The purpose of the fee is to recover costs associated with the development of data collections included in such sites. Your institution may already be a subscriber. Follow the links above to find out more about the data in these sites and their terms of usage.
Gas phase thermochemistry data
Go To: Top, Reaction 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:
DRB - Donald R. Burgess, Jr.
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | 176.7 ± 3.1 | 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°gas | 175.0 ± 1.5 | kJ/mol | Ccr | Rakus, Verevkin, et al., 1994 | ALS |
ΔfH°gas | 166.9 ± 4.1 | kJ/mol | Ccb | Sabbah, 1991 | see Sabbah and Antipine, 1987; ALS |
Constant pressure heat capacity of gas
Cp,gas (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
39.65 | 50. | Dorofeeva O.V., 1989 | Recommended values are also reproduced in the reference book [ Frenkel M., 1994]. These statistically calculated S(T) values agree with experimental ones within 1 J/mol*K.; GT |
57.90 | 100. | ||
81.47 | 150. | ||
109.90 | 200. | ||
156.72 | 273.15 | ||
173.1 ± 1.0 | 298.15 | ||
174.31 | 300. | ||
236.02 | 400. | ||
287.48 | 500. | ||
328.52 | 600. | ||
361.28 | 700. | ||
387.83 | 800. | ||
409.68 | 900. | ||
427.89 | 1000. | ||
443.21 | 1100. | ||
456.17 | 1200. | ||
467.22 | 1300. | ||
476.68 | 1400. | ||
484.83 | 1500. |
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 as indicated in comments:
B - John E. Bartmess
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
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
C13H9- + =
By formula: C13H9- + H+ = C13H10
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1466. ± 8.4 | kJ/mol | D-EA | Römer, Janaway, et al., 1997 | gas phase; B |
ΔrH° | 1472. ± 8.8 | kJ/mol | G+TS | Taft and Bordwell, 1988 | gas phase; B |
ΔrH° | 1478. ± 11. | kJ/mol | G+TS | Cumming and Kebarle, 1978 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1434. ± 8.8 | kJ/mol | H-TS | Römer, Janaway, et al., 1997 | gas phase; B |
ΔrG° | 1439. ± 8.4 | kJ/mol | IMRE | Taft and Bordwell, 1988 | gas phase; B |
ΔrG° | 1446. ± 8.4 | kJ/mol | IMRE | Cumming and Kebarle, 1978 | gas phase; B |
By formula: C10H8+ + C13H10 = (C10H8+ • C13H10)
Bond type: Charge transfer bond (positive ion)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 61.1 | kJ/mol | PHPMS | Meot-Ner (Mautner), 1980 | gas phase; Entropy change calculated or estimated; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 120. | J/mol*K | N/A | Meot-Ner (Mautner), 1980 | gas phase; Entropy change calculated or estimated; M |
Free energy of reaction
ΔrG° (kJ/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
25. | 307. | PHPMS | Meot-Ner (Mautner), 1980 | gas phase; Entropy change calculated or estimated; M |
By formula: C12H8+ + C13H10 = (C12H8+ • C13H10)
Bond type: Charge transfer bond (positive ion)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 55.6 | kJ/mol | PHPMS | Meot-Ner (Mautner), 1980 | gas phase; Entropy change calculated or estimated; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 120. | J/mol*K | N/A | Meot-Ner (Mautner), 1980 | gas phase; Entropy change calculated or estimated; M |
Free energy of reaction
ΔrG° (kJ/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
23. | 283. | PHPMS | Meot-Ner (Mautner), 1980 | gas phase; Entropy change calculated or estimated; M |
By formula: C13H10+ + C13H10 = (C13H10+ • C13H10)
Bond type: Charge transfer bond (positive ion)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 69.0 | kJ/mol | PHPMS | Meot-Ner (Mautner), 1980 | gas phase; Entropy change calculated or estimated; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 120. | J/mol*K | N/A | Meot-Ner (Mautner), 1980 | gas phase; Entropy change calculated or estimated; M |
Free energy of reaction
ΔrG° (kJ/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
30. | 331. | PHPMS | Meot-Ner (Mautner), 1980 | gas phase; Entropy change calculated or estimated; M |
By formula: C13H11+ + C13H10 = (C13H11+ • C13H10)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 60.2 | kJ/mol | PHPMS | Meot-Ner (Mautner), 1980 | gas phase; Entropy change calculated or estimated; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 120. | J/mol*K | N/A | Meot-Ner (Mautner), 1980 | gas phase; Entropy change calculated or estimated; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 26. | kJ/mol | PHPMS | Meot-Ner (Mautner), 1980 | gas phase; Entropy change calculated or estimated; M |
By formula: 3H2 + C13H10 = C13H16
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -180. | kJ/mol | Eqk | Frye and Weitkamp, 1969 | gas phase; ALS |
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 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 C13H10+ (ion structure unspecified)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
IE (evaluated) | 7.91 ± 0.02 | eV | N/A | N/A | L |
Quantity | Value | Units | Method | Reference | Comment |
Proton affinity (review) | 831.5 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 803.8 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Electron affinity determinations
EA (eV) | Method | Reference | Comment |
---|---|---|---|
<0.278 ± 0.026 | ECD | Wojnarovits and Foldiak, 1981 | EA is an upper limit: Chen and Wentworth, 1989. G3MP2B3 calculations indicate an EA of ca. -0.1 eV, anion unbound.; B |
Proton affinity at 298K
Proton affinity (kJ/mol) | Reference | Comment |
---|---|---|
828.0 | 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 |
---|---|---|
800.8 | 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 |
---|---|---|---|
7.88 ± 0.05 | EQ | Mautner(Meot-Ner), 1980 | LLK |
8.52 | EI | Terlouw, Heerma, et al., 1974 | LLK |
7.89 ± 0.03 | PI | Potapov, Kardash, et al., 1972 | LLK |
7.93 ± 0.01 | PE | Dewar, Haselbach, et al., 1970 | RDSH |
8.42 | CTS | Mukherjee, 1969 | RDSH |
7.78 | CTS | Slifkin and Allison, 1967 | RDSH |
7.91 | PE | Ruscic, Kovac, et al., 1978 | Vertical value; LLK |
7.93 ± 0.02 | PE | Maier and Turner, 1972 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C13H9+ | 12.5 ± 0.1 | H | EI | Rapp, Staab, et al., 1970 | RDSH |
De-protonation reactions
C13H9- + =
By formula: C13H9- + H+ = C13H10
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1466. ± 8.4 | kJ/mol | D-EA | Römer, Janaway, et al., 1997 | gas phase; B |
ΔrH° | 1472. ± 8.8 | kJ/mol | G+TS | Taft and Bordwell, 1988 | gas phase; B |
ΔrH° | 1478. ± 11. | kJ/mol | G+TS | Cumming and Kebarle, 1978 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1434. ± 8.8 | kJ/mol | H-TS | Römer, Janaway, et al., 1997 | gas phase; B |
ΔrG° | 1439. ± 8.4 | kJ/mol | IMRE | Taft and Bordwell, 1988 | gas phase; B |
ΔrG° | 1446. ± 8.4 | kJ/mol | IMRE | Cumming and Kebarle, 1978 | gas phase; B |
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]
Rakus, Verevkin, et al., 1994
Rakus, K.; Verevkin, S.P.; Schatzer, J.; Beckhaus, H.-D.; Ruchardt, C.,
Thermochemistry and thermal decomposition of 9,9'-bifluorenyl and 9,9'-dimethyl-9,9'-bifluorenyl - the stabilization energy of 9-fluorenyl radicals,
Chem. Ber., 1994, 127, 1095-1103. [all data]
Sabbah, 1991
Sabbah, R.,
Thermodynamic study of fluorene and dibenzofuran,
Bull. Soc. Chim. Fr., 1991, 128, 350. [all data]
Sabbah and Antipine, 1987
Sabbah, R.; Antipine, I.,
Thermodynamic study on four polycycles. Relationship between their energy values and their structure,
Bull. Soc. Chim. Fr., 1987, 392-400. [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]
Frenkel M., 1994
Frenkel M.,
Thermodynamics of Organic Compounds in the Gas State, Vol. I, II, Thermodynamics Research Center, College Station, Texas, 1994, 1994. [all data]
Römer, Janaway, et al., 1997
Römer, B.; Janaway, G.; Brauman, J.I.,
Cyclopentadienyl, Indenyl, and Fluorenyl Anions: Gas-Phase and Solvation Energy Contributions to Electron Detachment Energies,
J. Am. Chem. Soc., 1997, 119, 9, 2249, https://doi.org/10.1021/ja961947x
. [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]
Cumming and Kebarle, 1978
Cumming, J.B.; Kebarle, P.,
Summary of gas phase measurements involving acids AH. Entropy changes in proton transfer reactions involving negative ions. Bond dissociation energies D(A-H) and electron affinities EA(A),
Can. J. Chem., 1978, 56, 1. [all data]
Meot-Ner (Mautner), 1980
Meot-Ner (Mautner), M.,
Dimer Cations of Polycyclic Aromatics: Experimental Bonding Energies and Resonance Stabilization,
J. Phys. Chem., 1980, 84, 21, 2724, https://doi.org/10.1021/j100458a012
. [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]
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]
Mautner(Meot-Ner), 1980
Mautner(Meot-Ner), M.,
Ion thermochemistry of low volatility compounds in the gas phase. 3. Polycyclic aromatics: Ionization energies, proton, and hydrogen affinities. Extrapolations to graphite,
J. Phys. Chem., 1980, 84, 2716. [all data]
Terlouw, Heerma, et al., 1974
Terlouw, J.K.; Heerma, W.; Frintrop, P.C.M.; Dijkstra, G.; Meinema, H.A.,
Electron-impact induced fragmentation of some heterocyclic-tin compounds,
J. Organomet. Chem., 1974, 64, 205. [all data]
Potapov, Kardash, et al., 1972
Potapov, V.K.; Kardash, I.E.; Sorokin, V.V.; Sokolov, S.A.; Evlasheva, T.I.,
Photoionization of heteroaromatic compounds,
Khim. Vys. Energ., 1972, 6, 392. [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]
Mukherjee, 1969
Mukherjee, T.K.,
Charge-transfer donor abilities of o,o'bridged biphenyls,
J. Phys. Chem., 1969, 73, 3442. [all data]
Slifkin and Allison, 1967
Slifkin, M.A.; Allison, A.C.,
Measurement of ionization potentials from contact charge transfer spectra,
Nature, 1967, 215, 949. [all data]
Ruscic, Kovac, et al., 1978
Ruscic, B.; Kovac, B.; Klasinc, L.; Gusten, H.,
Photoelectron spectroscopy of J. Heterocycl. Chem.. Fluorene analogues,
Z. Naturforsch. A:, 1978, 33, 1006. [all data]
Maier and Turner, 1972
Maier, J.P.; Turner, D.W.,
Steric inhibition of resonance studied by molecular photoelectron spectroscopy. Part I. Biphenyls,
Faraday Discuss. Chem. Soc., 1972, 54, 149. [all data]
Rapp, Staab, et al., 1970
Rapp, U.; Staab, H.A.; Wunsche, C.,
Skelettumlagerungen unter Elektronenbeschuss-IV: zur Struktur der C13H9- und C12H9N-Ionen bei Benzylidenaminobenztriazolen,
Org. Mass Spectrom., 1970, 3, 45. [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 EA Electron affinity IE (evaluated) Recommended ionization energy T Temperature ΔfH°gas Enthalpy of formation of gas at standard conditions ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔrS° Entropy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
- The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment. However, NIST makes no warranties to that effect, and NIST shall not be liable for any damage that may result from errors or omissions in the Database.
- Customer support for NIST Standard Reference Data products.