Phenazine
- Formula: C12H8N2
- Molecular weight: 180.2053
- IUPAC Standard InChIKey: PCNDJXKNXGMECE-UHFFFAOYSA-N
- CAS Registry Number: 92-82-0
- 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: Azophenylene; Dibenzo-p-diazine; Dibenzopyrazine; 9,10-Diazaanthracene; Dibenzoparadiazine
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, 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: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | 80.86 ± 0.81 | kcal/mol | Ccr | Sabbah and El Watik, 1991 | |
ΔfH°gas | 78.59 ± 0.69 | kcal/mol | Ccb | Leitao, Pilcher, et al., 1990 | |
ΔfH°gas | 82.12 ± 0.67 | kcal/mol | Ccb | Arshadi, 1980 |
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 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 | 57.67 ± 0.81 | kcal/mol | Ccr | Sabbah and El Watik, 1991 | ALS |
ΔfH°solid | 56.64 ± 0.48 | kcal/mol | Ccb | Leitao, Pilcher, et al., 1990 | ALS |
ΔfH°solid | 58.25 ± 0.55 | kcal/mol | Ccb | Arshadi, 1980 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°solid | -1459.5 ± 0.79 | kcal/mol | Ccr | Sabbah and El Watik, 1991 | ALS |
ΔcH°solid | -1458.5 ± 0.29 | kcal/mol | Ccb | Leitao, Pilcher, et al., 1990 | ALS |
ΔcH°solid | -1460.1 ± 0.41 | kcal/mol | Ccb | Arshadi, 1980 | ALS |
ΔcH°solid | -1461.0 ± 1.5 | kcal/mol | Ccb | Willis, 1947 | Reanalyzed by Cox and Pilcher, 1970, Original value = -1460.9 ± 1.4 kcal/mol; ALS |
Constant pressure heat capacity of solid
Cp,solid (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
56.00 | 298.15 | Sabbah and El Watik, 1991 | DH |
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:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tfus | 444. | K | N/A | McEachern, Sandoval, et al., 1975 | Uncertainty assigned by TRC = 2. K; TRC |
Tfus | 451. | K | N/A | Sangster and Irvine, 1956 | Uncertainty assigned by TRC = 3. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 23. ± 2. | kcal/mol | AVG | N/A | Average of 11 values; Individual data points |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
15.8 ± 0.02 | 450. | Chirico, Kazakov, et al., 2010 | AC |
15.7 ± 0.02 | 460. | Chirico, Kazakov, et al., 2010 | AC |
15.5 ± 0.02 | 470. | Chirico, Kazakov, et al., 2010 | AC |
Enthalpy of sublimation
ΔsubH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
23.176 | 298.15 | N/A | Sabbah and El Watik, 1992 | DH |
22.5 ± 0.1 | 354. | N/A | Chirico, Kazakov, et al., 2010 | AC |
22.2 ± 0.1 | 354. | N/A | Sabbah and El Watik, 1991 | AC |
22.1 | 295. | N/A | Stephenson and Malanowski, 1987 | Based on data from 280. to 318. K.; AC |
21.6 ± 0.4 | 281.2 | V | McEachern, Sandoval, et al., 1975, 2 | hfusion=5.00±0.17 kcal/mol; ALS |
21.6 ± 0.41 | 281. to 293. | LE | McEachern, Sandoval, et al., 1975, 2 | AC |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
4.5124 | 447.89 | N/A | Sabbah and El Watik, 1992 | DH |
4.5124 | 447.89 | N/A | Sabbah and El Watik, 1991 | DH |
5.956 | 447.9 | AC | Chirico, Kazakov, et al., 2010 | AC |
5.000 | 450.2 | DSC | McEachern, Sandoval, et al., 1975, 2 | 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 evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias
Data compiled as indicated in comments:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
B - John E. Bartmess
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Proton affinity (review) | 224.3 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 217.1 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Electron affinity determinations
EA (eV) | Method | Reference | Comment |
---|---|---|---|
1.31 ± 0.10 | IMRE | Dillow and Kebarle, 1989 | ΔGea(423 K) = -29.5 kcal/mol; ΔSea =-1.5, taken as that of anthracene, from Kebarle and Chowdhury, 1987. 9,10-diazaanthracene; B |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
8.33 | PE | Hush, Cheung, et al., 1975 | LLK |
8.44 ± 0.02 | PE | Maier, Muller, et al., 1975 | Vertical value; LLK |
8.33 ± 0.02 | PE | Hush, Cheung, et al., 1975 | Vertical value; LLK |
IR 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.
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Gas Phase Spectrum
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Additional Data
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Owner | NIST Standard Reference Data Program Collection (C) 2018 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
---|---|
Origin | NIST Mass Spectrometry Data Center |
State | gas |
Instrument | HP-GC/MS/IRD |
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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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 | Japan AIST/NIMC Database- Spectrum MS-NW- 113 |
NIST MS number | 228361 |
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.
Data compiled by: Victor Talrose, Eugeny B. Stern, Antonina A. Goncharova, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina
Spectrum
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Additional Data
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Download spectrum in JCAMP-DX format.
Source | VanAllan, Reynolds, et al., 1962 |
---|---|
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. 3183 |
Instrument | n.i.g. |
Melting point | 176.5 |
Gas Chromatography
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, 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: NIST Mass Spectrometry Data Center, William E. Wallace, director
Kovats' RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Packed | SE-30 | 1703. | Ramsey, Lee, et al., 1980 | He, Chromosorb G HP (80-100 mesh); Column length: 1.5 m; Program: not specified |
Normal alkane RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Ultra-1 | 1670. | Okumura, 1991 | 25. m/0.32 mm/0.25 μm, He, 3. K/min; Tstart: 80. C; Tend: 260. C |
Normal alkane RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Ultra-1 | 1666. | Tameo and Kiyos, 1991 | Program: not specified |
Capillary | OV-1, SE-30, Methyl silicone, SP-2100, OV-101, DB-1, etc. | 1703. | Waggott and Davies, 1984 | Hydrogen; Column length: 50. m; Column diameter: 0.32 mm; Program: not specified |
Other | Methyl Silicone | 1703. | Ardrey and Moffat, 1981 | Program: not specified |
Normal alkane RI, polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Carbowax 20M | 2557. | Tameo and Kiyos, 1991 | Program: not specified |
Lee's RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | SE-52 | 294.37 | Vassilaros, Kong, et al., 1982 | 20. m/0.30 mm/0.25 μm, H2, 40. C @ 2. min, 4. K/min; Tend: 265. C |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, 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.
Sabbah and El Watik, 1991
Sabbah, R.; El Watik, L.,
Etude thermodynamique de la molecule de phenazine,
Thermochim. Acta, 1991, 176, 163-171. [all data]
Leitao, Pilcher, et al., 1990
Leitao, M.L.; Pilcher, G.; Acree, W.E., Jr.; Zvaigzne, A.I.; Tucker, S.A.; Ribeiro Da Silva, M.D.M.C.,
Enthalpies of combustion of phenazine N-oxide, phenazine, benzofuroxan, and benzofurazan: the dissociation entrhalpies of the (N-O) bonds,
J. Chem. Thermodyn., 1990, 22, 923-928. [all data]
Arshadi, 1980
Arshadi, M.R.,
Enthalpies of combustion and formation of phenazine and 2,1,3-benzoxadiazole,
J. Chem. Thermodyn., 1980, 12, 903-906. [all data]
Willis, 1947
Willis, J.B.,
The heats of combustion of some organic bases and their salts. The resonance energies of acridine and phenazine,
Trans. Faraday Soc., 1947, 43, 97-102. [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]
McEachern, Sandoval, et al., 1975
McEachern, D.M.; Sandoval, O.; Iniguez, J.C.,
Vapor pressures, derived enthalpies of sublimation, enthalpies of fusion, and resonance energies of acridine and phenazine,
J. Chem. Thermodyn., 1975, 7, 299. [all data]
Sangster and Irvine, 1956
Sangster, R.C.; Irvine, J.W.,
Study of Organic Scintillators,
J. Chem. Phys., 1956, 24, 670. [all data]
Chirico, Kazakov, et al., 2010
Chirico, Robert D.; Kazakov, Andrei F.; Steele, William V.,
Thermodynamic properties of three-ring aza-aromatics. 1. Experimental results for phenazine and acridine, and mutual validation of experiments and computational methods,
The Journal of Chemical Thermodynamics, 2010, 42, 5, 571-580, https://doi.org/10.1016/j.jct.2009.11.010
. [all data]
Sabbah and El Watik, 1992
Sabbah, R.; El Watik, L.,
Thermodynamic study of anthrone, counmarin and phenazine,
J. Therm. Anal., 1992, 38, 803-809. [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]
McEachern, Sandoval, et al., 1975, 2
McEachern, D.M.; Sandoval, O.; Iniguez, J.C.,
Vapor pressures, derived enthalpies of sublimation, enthalpies of fusion, and resonance energies of acridine and phenazine,
J. Chem. Thermodyn., 1975, 7, 299-306. [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]
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]
Maier, Muller, et al., 1975
Maier, J.P.; Muller, J.-F.; Kubota, T.; Yamakawa, M.,
183. Ionisation energies and the electronic structures of the N-oxides of azanaphthalenes and azaanthracenes,
Helv. Chim. Acta, 1975, 58, 1641. [all data]
VanAllan, Reynolds, et al., 1962
VanAllan, J.A.; Reynolds, G.A.; Adel, R.E.,
Polynuclear heterocycles. I. 1H-benzo[b]pyrido[1,2,3-mn]phenoxazin-1-one and related substances,
J. Org. Chem., 1962, 27, 1659-1664. [all data]
Ramsey, Lee, et al., 1980
Ramsey, J.D.; Lee, T.D.; Osselton, M.D.; Moffat, A.C.,
Gas-liquid chromatographic retention indices of 296 non-drug substances on SE-30 or OV-1 likely to be encountered in toxicological analyses,
J. Chromatogr., 1980, 184, 2, 185-206, https://doi.org/10.1016/S0021-9673(00)85641-1
. [all data]
Okumura, 1991
Okumura, T.,
retention indices of environmental chemicals on methyl silicone capillary column,
Journal of Environmental Chemistry (Japan), 1991, 1, 2, 333-358, https://doi.org/10.5985/jec.1.333
. [all data]
Tameo and Kiyos, 1991
Tameo, O.; Kiyos, I.,
Simultaneous determination of pesticides by capillary gas chromatography,
Cannot be traslated (in Japan), 1991, 14, 2, 109-122. [all data]
Waggott and Davies, 1984
Waggott, A.; Davies, I.W.,
Identification of organic pollutants using linear temperature programmed retention indices (LTPRIs) - Part II, 1984, retrieved from http://dwi.defra.gov.uk/research/completed-research/reports/dwi0383.pdf. [all data]
Ardrey and Moffat, 1981
Ardrey, R.E.; Moffat, A.C.,
Gas-liquid chromatographic retention indices of 1318 substances of toxicological interest on SE-30 or OV-1 stationary phase,
J. Chromatogr., 1981, 220, 3, 195-252, https://doi.org/10.1016/S0021-9673(00)81925-1
. [all data]
Vassilaros, Kong, et al., 1982
Vassilaros, D.L.; Kong, R.C.; Later, D.W.; Lee, M.L.,
Linear retention index system for polycyclic aromatic compounds. Critical evaluation and additional indices,
J. Chromatogr., 1982, 252, 1-20, https://doi.org/10.1016/S0021-9673(01)88394-1
. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, References
- Symbols used in this document:
Cp,solid Constant pressure heat capacity of solid EA Electron affinity Tfus Fusion (melting) point 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 ΔvapH Enthalpy of vaporization - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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