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
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Reaction thermochemistry data
Go To: Top, 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° | 350.5 ± 2.0 | kcal/mol | D-EA | Römer, Janaway, et al., 1997 | gas phase; B |
ΔrH° | 351.7 ± 2.1 | kcal/mol | G+TS | Taft and Bordwell, 1988 | gas phase; B |
ΔrH° | 353.3 ± 2.6 | kcal/mol | G+TS | Cumming and Kebarle, 1978 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 342.7 ± 2.1 | kcal/mol | H-TS | Römer, Janaway, et al., 1997 | gas phase; B |
ΔrG° | 344.0 ± 2.0 | kcal/mol | IMRE | Taft and Bordwell, 1988 | gas phase; B |
ΔrG° | 345.5 ± 2.0 | kcal/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° | 14.6 | kcal/mol | PHPMS | Meot-Ner (Mautner), 1980 | gas phase; Entropy change calculated or estimated; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 28. | cal/mol*K | N/A | Meot-Ner (Mautner), 1980 | gas phase; Entropy change calculated or estimated; M |
Free energy of reaction
ΔrG° (kcal/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
6.0 | 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° | 13.3 | kcal/mol | PHPMS | Meot-Ner (Mautner), 1980 | gas phase; Entropy change calculated or estimated; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 28. | cal/mol*K | N/A | Meot-Ner (Mautner), 1980 | gas phase; Entropy change calculated or estimated; M |
Free energy of reaction
ΔrG° (kcal/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
5.4 | 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° | 16.5 | kcal/mol | PHPMS | Meot-Ner (Mautner), 1980 | gas phase; Entropy change calculated or estimated; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 28. | cal/mol*K | N/A | Meot-Ner (Mautner), 1980 | gas phase; Entropy change calculated or estimated; M |
Free energy of reaction
ΔrG° (kcal/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
7.2 | 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° | 14.4 | kcal/mol | PHPMS | Meot-Ner (Mautner), 1980 | gas phase; Entropy change calculated or estimated; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 28. | cal/mol*K | N/A | Meot-Ner (Mautner), 1980 | gas phase; Entropy change calculated or estimated; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 6.1 | kcal/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° | -42. | kcal/mol | Eqk | Frye and Weitkamp, 1969 | gas phase; ALS |
References
Go To: Top, Reaction thermochemistry data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
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]
Notes
Go To: Top, Reaction thermochemistry data, References
- Symbols used in this document:
T Temperature 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
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