Benzo[c]cinnoline
- Formula: C12H8N2
- Molecular weight: 180.2053
- IUPAC Standard InChI: InChI=1S/C12H8N2/c1-3-7-11-9(5-1)10-6-2-4-8-12(10)14-13-11/h1-8H
- IUPAC Standard InChIKey: SWJXWSAKHXBQSY-UHFFFAOYSA-N
- CAS Registry Number: 230-17-1
- 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: 9,10-Diazaphenanthrene; Diphenylenazone; Phenazone; Phenazone (three-ring system); 2,2'-Azobiphenyl; 3,4-Benzocinnoline; 5,6-Phenanthroline; o-Diphenyleneazine; 5,6-Diazaphenanthrene; NSC 86935
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Phase change data
Go To: Top, 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:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
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 |
|---|---|---|---|---|---|
| ΔsubH° | 96.55 ± 0.90 | kJ/mol | C | Hussein and Akasheh, 1985 | ALS |
| ΔsubH° | 96.6 | kJ/mol | N/A | Hussein and Akasheh, 1985 | DRB |
| ΔsubH° | 101.68 ± 0.18 | kJ/mol | V | Schulze, Petrick, et al., 1977 | ALS |
Enthalpy of sublimation
| ΔsubH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 101.7 ± 0.2 | 340. | ME | Schulte, Petrick, et al., 1977 | Based on data from 320. to 360. K. See also Stephenson and Malanowski, 1987.; AC |
Enthalpy of fusion
| ΔfusH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 20.900 | 429. | N/A | Schulze, Petrick, et al., 1977 | DH |
| 20.92 | 432.2 | DTA | Schulte, Petrick, et al., 1977 | AC |
Gas phase ion energetics data
Go To: Top, 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 compiled as indicated in comments:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
B - John E. Bartmess
Electron affinity determinations
| EA (eV) | Method | Reference | Comment |
|---|---|---|---|
| 0.92 ± 0.10 | IMRE | Dillow and Kebarle, 1989 | ΔGea(423 K) = -20.6 kcal/mol; ΔSea =-1.5, taken as that of anthracene, from Kebarle and Chowdhury, 1987.1,2-diazaphenanthrene.; B |
Ionization energy determinations
| IE (eV) | Method | Reference | Comment |
|---|---|---|---|
| 7.9 | PE | Hush, Cheung, et al., 1975 | LLK |
| ~8.69 ± 0.02 | PE | Hush, Cheung, et al., 1975 | Vertical value; LLK |
References
Go To: Top, 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.
Hussein and Akasheh, 1985
Hussein, A.; Akasheh, T.S.,
Heat of combustion of heterocyclic compounds. Part II.,
Dirasat - Univ. Jordan, 1985, 12, 65-72. [all data]
Schulze, Petrick, et al., 1977
Schulze, F.W.; Petrick, H.J.; Cammenga, H.K.,
Thermodynamic properties of structural analogues benzo[c]cinnoline, trans-azobenzene, and cis-azobenzene,
Z. Phys. Chem. (Neue Folge), 1977, 107, 1-19. [all data]
Schulte, Petrick, et al., 1977
Schulte, F.W.; Petrick, H.-J.; Cammenga, H.K.; Klinge, H.,
Z. Phys. Chem. (Frankfurt), 1977, 107, 1. [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]
Dillow and Kebarle, 1989
Dillow, G.W.; Kebarle, P.,
Electron Affinities of aza-substituted polycyclic aromatic hydrocarbons,
Can. J. Chem., 1989, 67, 10, 1628, https://doi.org/10.1139/v89-249
. [all data]
Kebarle and Chowdhury, 1987
Kebarle, P.; Chowdhury, S.,
Electron affinities and electron transfer reactions,
Chem. Rev., 1987, 87, 513. [all data]
Hush, Cheung, et al., 1975
Hush, N.S.; Cheung, A.S.; Hilton, P.R.,
Binding energies of π- and "lone pair"-levels in mono- and diaza-phenanthrenes and anthracenes: an He(I) photoelectron spectroscopic study,
J. Electron Spectrosc. Relat. Phenom., 1975, 7, 385. [all data]
Notes
Go To: Top, Phase change data, Gas phase ion energetics data, References
- Symbols used in this document:
EA Electron affinity ΔfusH Enthalpy of fusion ΔsubH Enthalpy of sublimation ΔsubH° Enthalpy of sublimation at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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