Phenanthridine
- Formula: C13H9N
- Molecular weight: 179.2173
- IUPAC Standard InChIKey: RDOWQLZANAYVLL-UHFFFAOYSA-N
- CAS Registry Number: 229-87-8
- 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: Benzo[c]quinoline; 3,4-Benzoisoquinoline; 3,4-Benzoquinoline; 6-Phenanthridine; 9-Azaphenanthrene
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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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | 57.5 ± 1.0 | kcal/mol | Ccr | Steele, Chirico, et al., 1989 |
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 | 33.92 ± 0.33 | kcal/mol | Ccr | Steele, Chirico, et al., 1989 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°solid | -1563.76 ± 0.29 | kcal/mol | Ccr | Steele, Chirico, et al., 1989 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°solid,1 bar | 49.214 | cal/mol*K | N/A | Steele, Chirico, et al., 1989 | DH |
S°solid,1 bar | 49.214 | cal/mol*K | N/A | Steele, Chirico, et al., 1988 | DH |
S°solid,1 bar | 49.204 | cal/mol*K | N/A | Steele, Chirico, et al., 1986 | DH |
Constant pressure heat capacity of solid
Cp,solid (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
48.248 | 298.15 | Steele, Chirico, et al., 1989 | T = 5 to 500 K.; DH |
48.248 | 298.15 | Steele, Chirico, et al., 1988 | T = 5 to 500 K.; DH |
48.229 | 298.15 | Steele, Chirico, et al., 1986 | T = 6 to 450 K.; 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:
BS - Robert L. Brown and Stephen E. Stein
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.
CAL - James S. Chickos, William E. Acree, Jr., Joel F. Liebman, Students of Chem 202 (Introduction to the Literature of Chemistry), University of Missouri -- St. Louis
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tfus | 379.4 | K | N/A | Cumper, Ginman, et al., 1962 | Uncertainty assigned by TRC = 1. K; TRC |
Tfus | 379.65 | K | N/A | Cumper, Ginman, et al., 1962 | Uncertainty assigned by TRC = 1. K; TRC |
Tfus | 379.65 | K | N/A | Taylor and Kalenda, 1954 | Uncertainty assigned by TRC = 1.5 K; TRC |
Tfus | 372.65 | K | N/A | Taylor and Martin, 1952 | Uncertainty assigned by TRC = 2. K; TRC |
Tfus | 377. | K | N/A | Pictet, 1905 | Uncertainty assigned by TRC = 2. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 379.94 | K | N/A | Steele, Chirico, et al., 1989, 2 | Uncertainty assigned by TRC = 0.02 K; extrapolated from T-1/f plot, IPTS-68; TRC |
Ttriple | 379.74 | K | N/A | Steele, Chirico, et al., 1988, 2 | Crystal phase 1 phase; Uncertainty assigned by TRC = 0.02 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 23.6 ± 0.96 | kcal/mol | C | Steele, Chirico, et al., 1989 | ALS |
ΔsubH° | 23.6 | kcal/mol | N/A | Steele, Chirico, et al., 1989 | DRB |
ΔsubH° | 23.6 | kcal/mol | N/A | Steele, Chirico, et al., 1989 | AC |
Reduced pressure boiling point
Tboil (K) | Pressure (atm) | Reference | Comment |
---|---|---|---|
622.2 | 1.01 | Aldrich Chemical Company Inc., 1990 | BS |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
17.8 ± 0.02 | 380. | IPM | Steele, Chirico, et al., 1989 | Based on data from 383. to 473. K.; AC |
17.1 ± 0.02 | 420. | IPM | Steele, Chirico, et al., 1989 | Based on data from 383. to 473. K.; AC |
16.5 ± 0.02 | 460. | IPM | Steele, Chirico, et al., 1989 | Based on data from 383. to 473. K.; AC |
Enthalpy of sublimation
ΔsubH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
23.9 ± 2.4 | 306. | ME | Oja and Suuberg, 1998 | Based on data from 288. to 323. K.; AC |
22.6 ± 1. | 308. | ME | McEachern, Iniguez, et al., 1975 | Based on data from 288. to 323. K. See also Stephenson and Malanowski, 1987.; AC |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
5.457 | 379.7 | Domalski and Hearing, 1996 | AC |
Entropy of fusion
ΔfusS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
0.01 | 354. | Domalski and Hearing, 1996 | CAL |
14.37 | 379.7 |
Temperature of phase transition
Ttrs (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|
354.16 | crystaline, II | crystaline, I | Steele, Chirico, et al., 1986 | DH |
379.742 | crystaline, I | liquid | Steele, Chirico, et al., 1986 | DH |
Enthalpy of phase transition
ΔHtrs (kcal/mol) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
0.004969 | 354.0 | crystaline, II | crystaline, I | Steele, Chirico, et al., 1989 | Extrapolated value.; DH |
5.4567 | 379.74 | crystaline, I | liquid | Steele, Chirico, et al., 1989 | DH |
0.004969 | 354.0 | crystaline, II | crystaline, I | Steele, Chirico, et al., 1988 | Extrapolated value.; DH |
5.4567 | 379.74 | crystaline, I | liquid | Steele, Chirico, et al., 1988 | DH |
Entropy of phase transition
ΔStrs (cal/mol*K) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
0.014 | 354.0 | crystaline, II | crystaline, I | Steele, Chirico, et al., 1989 | Extrapolated; DH |
14.37 | 379.74 | crystaline, I | liquid | Steele, Chirico, et al., 1989 | DH |
0.014 | 354.0 | crystaline, II | crystaline, I | Steele, Chirico, et al., 1988 | Extrapolated; DH |
14.37 | 379.74 | crystaline, I | liquid | Steele, Chirico, et al., 1988 | DH |
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
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
View reactions leading to C13H9N+ (ion structure unspecified)
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
8.31 ± 0.02 | PE | Hush, Cheung, et al., 1975 | LLK |
8.4 ± 0.1 | CTS | Farrell and Newton, 1966 | RDSH |
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)
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, 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: 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 | NIST Mass Spectrometry Data Center, 1990. |
NIST MS number | 118684 |
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 | Wiesner, Figdor, et al., 1952 |
---|---|
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. 644 |
Instrument | n.i.g. |
Melting point | 107.4 |
Boiling point | 349 |
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 | 1840. | Rostad and Pereira, 1986 | 30. m/0.26 mm/0.25 μm, He, 50. C @ 4. min, 6. K/min, 300. C @ 20. min |
Capillary | SE-52 | 1787. | Beernaert, 1979 | He, 50. C @ 5. min, 6. K/min; Column length: 33.3 m; Column diameter: 0.50 mm; Tend: 320. C |
Normal alkane RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Polydimethyl siloxane, unknown content of Ph-groups | 1840. | Geldon, 1989 | Program: not specified |
Capillary | Polydimethyl siloxane, unknown content of Ph-groups | 1841. | Geldon, 1989 | Program: not specified |
Lee's RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-5 | 308.1 | Durlak, Biswas, et al., 1998 | 30. m/0.25 mm/0.25 μm, 15. K/min; Tstart: 50. C; Tend: 300. C |
Capillary | SPB-5 | 307.3 | Knobloch and Engewald, 1993 | 40. C @ 2. min, 4. K/min; Column length: 30. m; Column diameter: 0.25 mm; Tend: 300. C |
Capillary | SE-52 | 308.27 | Hasegawa, Usami, et al., 1990 | 2. K/min; Column length: 12. m; Column diameter: 0.25 mm; Tstart: 50. C; Tend: 270. C |
Capillary | OV-101 | 307.45 | Blanco, Blanco, et al., 1989 | H2, 4. K/min; Column length: 25. m; Column diameter: 0.22 mm; Tstart: 50. C; Tend: 300. C |
Capillary | DB-5 | 307.30 | Rostad and Pereira, 1986 | 30. m/0.26 mm/0.25 μm, He, 50. C @ 4. min, 6. K/min, 300. C @ 20. min |
Capillary | SE-52 | 307.94 | Vassilaros, Kong, et al., 1982 | 20. m/0.30 mm/0.25 μm, H2, 40. C @ 2. min, 4. K/min; Tend: 265. C |
Capillary | SE-52 | 308.79 | Lee, Vassilaros, et al., 1979 | 12. m/0.3 mm/0.34 μm, He, 2. K/min; Tstart: 50. C; Tend: 250. C |
Lee's RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-5 | 306.3 | Lundstedt, Haglund, et al., 2003 | 30. m/0.25 mm/0.25 μm; Program: not specified |
Capillary | DB-5 | 311.0 | Lundstedt, Haglund, et al., 2003 | 30. m/0.25 mm/0.25 μm; Program: not specified |
Capillary | SE-54 | 307.03 | Guillen, Iglesias, et al., 1992 | Program: not specified |
Capillary | SE-52 | 307.94 | Hasegawa, Usami, et al., 1990 | Column length: 12. m; Column diameter: 0.25 mm; Program: not specified |
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.
Steele, Chirico, et al., 1989
Steele, W.V.; Chirico, R.D.; Hossenlopp, I.A.; Nguyen, A.; Smith, N.K.; Gammon, B.E.,
The thermodynamic properties of the five benzoquinolines,
J. Chem. Thermodyn., 1989, 21, 81-107. [all data]
Steele, Chirico, et al., 1988
Steele, W.V.; Chirico, R.D.; Hossenlopp, I.A.; Nguyen, A.,
The thermodynamic properties of the five benzoquinolines,
NIPER Report, 1988, 337, 59p. [all data]
Steele, Chirico, et al., 1986
Steele, W.V.; Chirico, R.D.; Collier, W.B.; Hossenlopp, I.A.; Nguyen, A.; Strube, M.M.,
Thermochemical and thermophysical properties of organic nitrogen compounds found in fossil materials,
NIPER Report, 1986, 188, 112p. [all data]
Cumper, Ginman, et al., 1962
Cumper, C.W.N.; Ginman, R.F.A.; Vogel, A.I.,
Physical properties and chemical constitution. The electric dipole moments of phenyl derivatives of some n-heterocyclic molecules,
J. Chem. Soc., 1962, 1962, 4518. [all data]
Taylor and Kalenda, 1954
Taylor, E.C.; Kalenda, N.W.,
Improved phenanthridine syntheses with poly-phosphoric acid.,
J. Am. Chem. Soc., 1954, 76, 1699. [all data]
Taylor and Martin, 1952
Taylor, E.C.; Martin, A.E.,
A new synthesis of phenanthridine.,
J. Am. Chem. Soc., 1952, 74, 6295. [all data]
Pictet, 1905
Pictet, A.,
The Pyrogenic Transformation of Methylpyrroles to Pyridine Derivatives,
Ber. Dtsch. Chem. Ges., 1905, 38, 1946. [all data]
Steele, Chirico, et al., 1989, 2
Steele, W.V.; Chirico, R.D.; Hossenlopp, I.A.; Nguyen, A.; Smith, N.K.; Gammon, B.E.,
The thermodynamic properties of the five benzoquinolines,
J. Chem. Thermodyn., 1989, 21, 81. [all data]
Steele, Chirico, et al., 1988, 2
Steele, W.V.; Chirico, R.D.; Knipmeyer, S.E.; Smith, N.K.,
, Report, NIPPR-395, 1988. [all data]
Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc.,
Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [all data]
Oja and Suuberg, 1998
Oja, Vahur; Suuberg, Eric M.,
Vapor Pressures and Enthalpies of Sublimation of Polycyclic Aromatic Hydrocarbons and Their Derivatives,
J. Chem. Eng. Data, 1998, 43, 3, 486-492, https://doi.org/10.1021/je970222l
. [all data]
McEachern, Iniguez, et al., 1975
McEachern, D.M.; Iniguez, J.C.; Ornelas, H.C.,
Enthalpies of combustion and sublimation and vapor pressures of three benzoquinolines,
J. Chem. Eng. Data, 1975, 20, 226-228. [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]
Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D.,
Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III,
J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985
. [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]
Farrell and Newton, 1966
Farrell, P.G.; Newton, J.,
Ionization potentials of primary aromatic amines and aza-hydrocarbons,
Tetrahedron Lett., 1966, 5517. [all data]
Wiesner, Figdor, et al., 1952
Wiesner, K.; Figdor, S.K.; Bartlett, M.F.; Henderson, D.R.,
Garryha alkaloids. I. The structure of garryine and veatchine,
Can. J. Chem., 1952, 30, 608-626. [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]
Beernaert, 1979
Beernaert, H.,
Gas Chromatographic Analysis of Polyclylic Aromatic Hydrocarbons,
J. Chromatogr., 1979, 173, 1, 109-118, https://doi.org/10.1016/S0021-9673(01)80450-7
. [all data]
Geldon, 1989
Geldon, A.L.,
Ground Water Hydrology of the Central Raton Basin, Colorado and New Mexico, US Geological Survey, US Government Printing Office, 1989, 104. [all data]
Durlak, Biswas, et al., 1998
Durlak, S.K.; Biswas, P.; Shi, J.; Bernhard, M.J.,
Characterization of polycyclic aromatic hydrocarbon particulate and gaseous emissions from polystyrene combustion,
Environ. Sci. Technol., 1998, 32, 15, 2301-2307, https://doi.org/10.1021/es9709031
. [all data]
Knobloch and Engewald, 1993
Knobloch, T.; Engewald, W.,
Identification of some polar polycyclic compounds in emissions from brown-coal-fired residential stoves,
J. Hi. Res. Chromatogr., 1993, 16, 4, 239-242, https://doi.org/10.1002/jhrc.1240160407
. [all data]
Hasegawa, Usami, et al., 1990
Hasegawa, K.; Usami, S.; Higashide, A.,
Analysis of amino polycyclic aromatic hydrocarbons and polycyclic aromatic nitrogen heterocycles,
Nippon Kagaku Kaishi, 1990, 7, 777-788, https://doi.org/10.1246/nikkashi.1990.777
. [all data]
Blanco, Blanco, et al., 1989
Blanco, C.G.; Blanco, J.; Bermejo, J.; Guillen, M.D.,
Capillary gas chromatography of some polycyclic aromatic compounds on several stationary phases,
J. Chromatogr., 1989, 465, 3, 378-385, https://doi.org/10.1016/S0021-9673(01)92675-5
. [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]
Lee, Vassilaros, et al., 1979
Lee, M.L.; Vassilaros, D.L.; White, C.M.; Novotny, M.,
Retention Indices for Programmed-Temperature Capillary-Column Gas Chromatography of Polycyclic Aromatic Hydrocarbons,
Anal. Chem., 1979, 51, 6, 768-773, https://doi.org/10.1021/ac50042a043
. [all data]
Lundstedt, Haglund, et al., 2003
Lundstedt, S.; Haglund, P.; Öberg, L.,
Degradation and formation of polycyclic aromatic compounds during bioslurry treatment of an aged gasworks soil,
Environ. Toxicol. Chem., 2003, 22, 7, 1413-1420, https://doi.org/10.1002/etc.5620220701
. [all data]
Guillen, Iglesias, et al., 1992
Guillen, M.D.; Iglesias, M.J.; Dominguez, A.; Blanco, C.G.,
Polynuclear aromatic hydrocarbon retention indices on SE-54 stationary phase of the volatile components of a coal tar pitch. Relationships between chromatographic retention and thermal reactivity,
J. Chromatogr., 1992, 591, 1-2, 287-295, https://doi.org/10.1016/0021-9673(92)80246-Q
. [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 S°solid,1 bar Entropy of solid at standard conditions (1 bar) Tboil Boiling point Tfus Fusion (melting) point Ttriple Triple point temperature Ttrs Temperature of phase transition ΔHtrs Enthalpy of phase transition ΔStrs Entropy of phase transition 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 ΔfusS Entropy 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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