Carbazole
- Formula: C12H9N
- Molecular weight: 167.2066
- IUPAC Standard InChI: InChI=1S/C12H9N/c1-3-7-11-9(5-1)10-6-2-4-8-12(10)13-11/h1-8,13H
- IUPAC Standard InChIKey: UJOBWOGCFQCDNV-UHFFFAOYSA-N
- CAS Registry Number: 86-74-8
- 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-Carbazole; Dibenzopyrrole; Dibenzo[b,d]pyrrole; Diphenylenimine; 9-Azafluorene; Diphenylenimide; Diphenyleneimine; USAF EK-600; SKF 20091; NSC 3498
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Gas phase thermochemistry data
Go To: Top, Condensed 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:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°gas | 49.00 ± 0.72 | kcal/mol | Ccb | Jimenez, Roux, et al., 1990 | ALS |
| ΔfH°gas | 50.10 ± 0.84 | kcal/mol | Ccr | Sabbah and Antipine, 1987 | ALS |
| ΔfH°gas | 53.27 | kcal/mol | N/A | Tavernier and Lamouroux, 1957 | Value computed using ΔfHsolid° value of 125.1±3.6 kj/mol from Tavernier and Lamouroux, 1957 and ΔsubH° value of 97.8 kj/mol from Tavernier and Lamouroux, 1957.; DRB |
Condensed phase thermochemistry 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:
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°solid | 24.31 ± 0.67 | kcal/mol | Ccb | Jimenez, Roux, et al., 1990 | ALS |
| ΔfH°solid | 26.72 ± 0.84 | kcal/mol | Ccr | Sabbah and Antipine, 1987 | ALS |
| ΔfH°solid | 29.90 ± 0.87 | kcal/mol | Ccb | Tavernier and Lamouroux, 1957 | Reanalyzed by Cox and Pilcher, 1970, Original value = 32.57 kcal/mol; Author's hf298_condensed=26.844 kcal/mol; ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°solid | -1460.3 ± 0.55 | kcal/mol | Ccb | Jimenez, Roux, et al., 1990 | ALS |
| ΔcH°solid | -1462.7 ± 0.81 | kcal/mol | Ccr | Sabbah and Antipine, 1987 | ALS |
| ΔcH°solid | -1461.8 | kcal/mol | Ccb | Zimmerman and Geisenfelder, 1961 | ALS |
| ΔcH°solid | -1465.93 ± 0.86 | kcal/mol | Ccb | Tavernier and Lamouroux, 1957 | Reanalyzed by Cox and Pilcher, 1970, Original value = -1468.629 kcal/mol; Author's hf298_condensed=26.844 kcal/mol; ALS |
Constant pressure heat capacity of solid
| Cp,solid (cal/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 46.37 | 298.15 | Jimenez, Roux, et al., 1990 | DH |
| 45.60 | 298.15 | Radomska and Radomski, 1980 | T = 180 to 410 K. Cp = 54.87 + 0.2328T + 7.477x10-4T2.; DH |
Reaction thermochemistry data
Go To: Top, Gas phase thermochemistry data, Condensed phase 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 by: John E. Bartmess
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
C12H8N- + =
By formula: C12H8N- + H+ = C12H9N
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 345.1 ± 2.1 | kcal/mol | G+TS | Taft and Bordwell, 1988 | gas phase |
| ΔrH° | 335.5 ± 5.0 | kcal/mol | EIAE | Muftakhov, Vasil'ev, et al., 1999 | gas phase |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 337.4 ± 2.0 | kcal/mol | IMRE | Taft and Bordwell, 1988 | gas phase |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Jimenez, Roux, et al., 1990
Jimenez, P.; Roux, M.V.; Turrion, C.,
Thermochemical properties of N-heterocyclic compounds. III. Enthalpies of combustion, vapour pressures and enthalpies of sublimation, and enthalpies of formation of 9H-carbazole, 9-methylcarbazole, and 9-ethylcarbazole,
J. Chem. Thermodyn., 1990, 22, 721-726. [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]
Tavernier and Lamouroux, 1957
Tavernier, P.; Lamouroux, M.,
Determinations calorimetriques relatives a vingt et une substances organiques,
Mem. Poudres, 1957, 39, 335-356. [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]
Zimmerman and Geisenfelder, 1961
Zimmerman, H.; Geisenfelder, H.,
Uber die Mesomerieenergie von Azolen,
Z. Electrochem., 1961, 65, 368-371. [all data]
Radomska and Radomski, 1980
Radomska, M.; Radomski, R.,
Calorimetric studies of binary systems of 1,3,5-trinitrobenzene with naphthalene, anthracene, and carbazole. I. Phase transitions and heat capacities of the pure components and charge-transfer complexes,
Thermochim. Acta, 1980, 40, 405-414. [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]
Muftakhov, Vasil'ev, et al., 1999
Muftakhov, M.V.; Vasil'ev, Y.V.; Khatymov, R.V.; Mazunov, V.A.; Takhistov, V.V.; Travkin, O.V.; Yakovleva, E.V.,
Thermochemistry of negatively charged ions. II. Energetics of formation of negative ions from acridanone and some of its derivatives,
Rapid Commun. Mass Spectrom., 1999, 13, 10, 912-923, https://doi.org/10.1002/(SICI)1097-0231(19990530)13:10<912::AID-RCM585>3.0.CO;2-W
. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, References
- Symbols used in this document:
Cp,solid Constant pressure heat capacity of solid ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°solid Enthalpy of formation of solid at standard conditions ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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