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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Gas phase thermochemistry data
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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 | 89.9 ± 1.2 | kcal/mol | Ccb | Hussein and Akasheh, 1985 | ALS |
| ΔfH°gas | 93.62 | kcal/mol | N/A | Schulze, Petrick, et al., 1977 | Value computed using ΔfHsolid° value of 295.1 kj/mol from Schulze, Petrick, et al., 1977 and ΔsubH° value of 96.6 kj/mol from Hussein and Akasheh, 1985.; DRB |
Condensed phase thermochemistry data
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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data compiled by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°solid | 66.78 ± 0.96 | kcal/mol | Ccb | Hussein and Akasheh, 1985 | |
| ΔfH°solid | 70.53 | kcal/mol | Ccb | Schulze, Petrick, et al., 1977 | |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°solid | -1468.6 ± 0.91 | kcal/mol | Ccb | Hussein and Akasheh, 1985 | |
| ΔcH°solid | -1472.4 ± 0.41 | kcal/mol | Ccb | Schulze, Petrick, et al., 1977 |
Phase change data
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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° | 23.08 ± 0.22 | kcal/mol | C | Hussein and Akasheh, 1985 | ALS |
| ΔsubH° | 23.1 | kcal/mol | N/A | Hussein and Akasheh, 1985 | DRB |
| ΔsubH° | 24.302 ± 0.043 | kcal/mol | V | Schulze, Petrick, et al., 1977 | ALS |
Enthalpy of sublimation
| ΔsubH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 24.31 ± 0.05 | 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 (kcal/mol) | Temperature (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 4.9952 | 429. | N/A | Schulze, Petrick, et al., 1977 | DH |
| 5.000 | 432.2 | DTA | Schulte, Petrick, et al., 1977 | AC |
Gas phase ion energetics data
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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 |
Mass spectrum (electron ionization)
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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Spectrum
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Additional Data
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Due to licensing restrictions, this spectrum cannot be downloaded.
| Owner | NIST Mass Spectrometry Data Center Collection (C) 2014 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
|---|---|
| Origin | D.HENNEBERG, MAX-PLANCK INSTITUTE, MULHEIM, WEST GERMANY |
| NIST MS number | 63392 |
UV/Visible spectrum
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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Spectrum
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Additional Data
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| Source | Badger and Pettit, 1951 |
|---|---|
| Owner | INEP CP RAS, NIST OSRD Collection (C) 2007 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
| Origin | INSTITUTE OF ENERGY PROBLEMS OF CHEMICAL PHYSICS, RAS |
| Source reference | RAS UV No. 9941 |
| Instrument | Beckman DU |
| Melting point | 157-159 |
Gas Chromatography
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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Van Den Dool and Kratz RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | DB-5 | 1933. | Rostad and Pereira, 1986 | 30. m/0.26 mm/0.25 μm, He, 50. C @ 4. min, 6. K/min, 300. C @ 20. min |
Lee's RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | DB-5 | 322.07 | Rostad and Pereira, 1986 | 30. m/0.26 mm/0.25 μm, He, 50. C @ 4. min, 6. K/min, 300. C @ 20. min |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, 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]
Badger and Pettit, 1951
Badger, G.M.; Pettit, R.,
J. Chem. Soc., 1951, 3199. [all data]
Rostad and Pereira, 1986
Rostad, C.E.; Pereira, W.E.,
Kovats and Lee retention indices determined by gas chromatography/mass spectrometry for organic compounds of environmental interest,
J. Hi. Res. Chromatogr. Chromatogr. Comm., 1986, 9, 6, 328-334, https://doi.org/10.1002/jhrc.1240090603
. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, References
- Symbols used in this document:
EA Electron affinity 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 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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