Carbazole
- Formula: C12H9N
- Molecular weight: 167.2066
- 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
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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 | 205.0 ± 3.0 | kJ/mol | Ccb | Jimenez, Roux, et al., 1990 | ALS |
ΔfH°gas | 209.6 ± 3.5 | kJ/mol | Ccr | Sabbah and Antipine, 1987 | ALS |
ΔfH°gas | 222.9 | kJ/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 |
Reaction thermochemistry data
Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), 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: 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° | 1444. ± 8.8 | kJ/mol | G+TS | Taft and Bordwell, 1988 | gas phase |
ΔrH° | 1404. ± 21. | kJ/mol | EIAE | Muftakhov, Vasil'ev, et al., 1999 | gas phase |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1412. ± 8.4 | kJ/mol | IMRE | Taft and Bordwell, 1988 | gas phase |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Mass spectrum (electron ionization), 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 as indicated in comments:
B - John E. Bartmess
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 C12H9N+ (ion structure unspecified)
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
7.57 ± 0.03 | PI | Potapov, Kardash, et al., 1972 | LLK |
7.6 ± 0.1 | EI | Rapp, Staab, et al., 1970 | RDSH |
7.2 ± 0.1 | EI | Riepe and Zander, 1969 | RDSH |
7.50 | PE | Ruscic, Kovac, et al., 1978 | Vertical value; LLK |
7.68 | PE | Haink, Adams, et al., 1974 | Vertical value; LLK |
De-protonation reactions
C12H8N- + =
By formula: C12H8N- + H+ = C12H9N
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1444. ± 8.8 | kJ/mol | G+TS | Taft and Bordwell, 1988 | gas phase; B |
ΔrH° | 1404. ± 21. | kJ/mol | EIAE | Muftakhov, Vasil'ev, et al., 1999 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1412. ± 8.4 | kJ/mol | IMRE | Taft and Bordwell, 1988 | gas phase; B |
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
View image of digitized spectrum (can be printed in landscape orientation).
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 | 113349 |
Gas Chromatography
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), 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, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Capillary | OV-1 | 160. | 1781. | Zhang, Chen, et al., 1997 | 25. m/0.2 mm/0.33 μm, N2 |
Capillary | OV-101 | 140. | 1761.1 | Gerasimenko, Kirilenko, et al., 1981 | N2; Column length: 50. m; Column diameter: 0.3 mm |
Kovats' RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Packed | SE-30 | 1784. | Ramsey, Lee, et al., 1980 | He, Chromosorb G HP (80-100 mesh); Column length: 1.5 m; Program: not specified |
Van Den Dool and Kratz RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | OV-1 | 1801.1 | Zhang, Shen, et al., 2000 | 25. m/0.2 mm/0.33 μm, 5. K/min; Tstart: 100. C; Tend: 180. C |
Capillary | OV-1 | 1820.5 | Zhang, Shen, et al., 2000 | 25. m/0.2 mm/0.33 μm, 5. K/min; Tstart: 100. C; Tend: 180. C |
Packed | SE-30 | 1810. | Peng, Ding, et al., 1988 | He, Supelcoport and Chromosorb, 40. C @ 4. min, 10. K/min, 250. C @ 60. min; Column length: 3.05 m |
Capillary | DB-5 | 1851. | 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-54 | 1806. | Weber, 1986 | 25. m/0.31 mm/0.17 μm, H2, 2. K/min; Tstart: 35. C |
Capillary | SE-54 | 1836. | Weber, 1986 | 25. m/0.31 mm/0.17 μm, H2, 2. K/min; Tstart: 35. C |
Capillary | SE-52 | 1766. | Beernaert, 1979 | He, 50. C @ 5. min, 6. K/min; Column length: 33.3 m; Column diameter: 0.50 mm; Tend: 320. C |
Capillary | SE-52 | 1838. | Cantuti, Cartoni, et al., 1965 | N2, 2.5 K/min; Column length: 50. m; Tstart: 100. C; Tend: 300. C |
Van Den Dool and Kratz RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | 5 % Phenyl methyl siloxane | 1823. | Yasuhara, Shiraishi, et al., 1997 | 25. m/0.31 mm/0.52 μm, He; Program: 50C(2min) => (20C/min) => 120C => (7C/min) => 310C(10min) |
Capillary | Methyl Silicone | 1789. | Oda, Ichikawa, et al., 1996 | Program: 50C (2min) => 20C/min => 160C => 5C/min => 210C => 10C/min => 300C |
Normal alkane RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-5 | 1841. | Grung, Lichtenthaler, et al., 2007 | 30. m/0.25 mm/0.25 μm, 5. K/min, 280. C @ 10. min; Tstart: 40. C |
Capillary | Ultra-1 | 1790. | Elizalde-González, Hutfliess, et al., 1996 | 50. m/0.2 mm/0.33 μm, H2, 3. K/min, 300. C @ 35. min; Tstart: 60. C |
Capillary | Ultra-1 | 1768. | 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 | Polydimethyl siloxane, unknown content of Ph-groups | 1849. | Geldon, 1989 | Program: not specified |
Capillary | Polydimethyl siloxane, unknown content of Ph-groups | 1852. | Geldon, 1989 | Program: not specified |
Other | Methyl Silicone | 1784. | Ardrey and Moffat, 1981 | Program: not specified |
Lee's RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-5MS | 308.63 | Chen, Keeran, et al., 2002 | 30. m/0.25 mm/0.5 μm, 40. C @ 1. min, 10. K/min; Tend: 310. C |
Capillary | DB-5MS | 309.24 | Chen, Keeran, et al., 2002 | 30. m/0.25 mm/0.5 μm, 40. C @ 1. min, 4. K/min; Tend: 310. C |
Capillary | SE-54 | 310.15 | Chen, 1996 | 4. K/min; Column length: 30. m; Column diameter: 0.25 mm; Tstart: 50. C; Tend: 300. C |
Capillary | OV-101 | 309.63 | 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 | 310.35 | Wise, Benner, et al., 1988 | 30. m/0.25 mm/0.25 μm, 40. C @ 2. min, 4. K/min, 280. C @ 5. min |
Capillary | DB-5 | 309.22 | 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 | 311.71 | 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 | 312.13 | 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 | HP-5MS | 309.8 | Wang, Li, et al., 2007 | 30. m/0.25 mm/0.25 μm, He; Program: 60C(2min) => 6C/min => 258C => 2C/min => 300C(4min) |
Capillary | HP-5MS | 309.80 | Wang, Li, et al., 2007, 2 | 30. m/0.25 mm/0.25 μm, He; Program: not specified |
Capillary | HP-5MS | 310.35 | Wang, Li, et al., 2007, 2 | 30. m/0.25 mm/0.25 μm, He; Program: not specified |
Capillary | HP-5MS | 311.71 | Wang, Li, et al., 2007, 2 | 30. m/0.25 mm/0.25 μm, He; Program: not specified |
Capillary | DB-5 | 307.9 | Lundstedt, Haglund, et al., 2003 | 30. m/0.25 mm/0.25 μm; Program: not specified |
Capillary | SE-54 | 312.13 | Chen, 1996 | Column length: 30. m; Column diameter: 0.25 mm; Program: not specified |
Capillary | SE-54 | 309.02 | Guillen, Iglesias, et al., 1992 | Program: not specified |
Capillary | OV-101 | 311.0 | Tucminen, Wickstrom, et al., 1986 | Program: not specified |
Capillary | OV-101 | 314.3 | Tucminen, Wickstrom, et al., 1986 | Program: not specified |
References
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), Gas Chromatography, 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]
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
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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
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Potapov, Kardash, et al., 1972
Potapov, V.K.; Kardash, I.E.; Sorokin, V.V.; Sokolov, S.A.; Evlasheva, T.I.,
Photoionization of heteroaromatic compounds,
Khim. Vys. Energ., 1972, 6, 392. [all data]
Rapp, Staab, et al., 1970
Rapp, U.; Staab, H.A.; Wunsche, C.,
Skelettumlagerungen unter Elektronenbeschuss-IV: zur Struktur der C13H9- und C12H9N-Ionen bei Benzylidenaminobenztriazolen,
Org. Mass Spectrom., 1970, 3, 45. [all data]
Riepe and Zander, 1969
Riepe, W.; Zander, M.,
Massenspektroskopische Untersuchungen an Carbazolen,
Z. Naturforsch., 1969, 24a, 2017. [all data]
Ruscic, Kovac, et al., 1978
Ruscic, B.; Kovac, B.; Klasinc, L.; Gusten, H.,
Photoelectron spectroscopy of J. Heterocycl. Chem.. Fluorene analogues,
Z. Naturforsch. A:, 1978, 33, 1006. [all data]
Haink, Adams, et al., 1974
Haink, H.J.; Adams, J.E.; Huber, J.R.,
The electronic structure of aromatic amines: photoelectron spectroscopy of diphenylamine, iminobibenzyl, acridan and carbazole,
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Zhang, M.; Chen, B.; Shen, S.; Chen, S.,
Compositional studies of high-temperature coal tar by g.c.-FT-i.r. analysis of middle oil fractions,
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Gerasimenko, Kirilenko, et al., 1981
Gerasimenko, V.A.; Kirilenko, A.V.; Nabivach, V.M.,
Capillary gas chromatography of aromatic compounds found in coal tar fractions,
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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,
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Zhang, Shen, et al., 2000
Zhang, M.-J.; Shen, S.-D.; Chen, S.-Y.; Sun, Y.-H.,
Analysis of heavy oil fractions in high-temperature coal tar by capillary gas chromatography/fourier transform infrared spectrometry,
Chin. J. Chromatogr., 2000, 18, 3, 241-246. [all data]
Peng, Ding, et al., 1988
Peng, C.T.; Ding, S.F.; Hua, R.L.; Yang, Z.C.,
Prediction of Retention Indexes I. Structure-Retention Index Relationship on Apolar Columns,
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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,
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Weber, 1986
Weber, L.,
Utilization of the Sadtler standard RI system in micropollution analyses,
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Beernaert, 1979
Beernaert, H.,
Gas Chromatographic Analysis of Polyclylic Aromatic Hydrocarbons,
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Cantuti, Cartoni, et al., 1965
Cantuti, V.; Cartoni, G.P.; Liberti, A.; Torri, A.G.,
Improved evaluation of polynuclear hydrocarbons in atmospheric dust by gas chromatography,
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Yasuhara, Shiraishi, et al., 1997
Yasuhara, A.; Shiraishi, H.; Nishikawa, M.; Yamamoto, T.; Uehiro, T.; Nakasugi, O.; Okumura, T.; Kenmotsu, K.; Fukui, H.; Nagase, M.; Ono, Y.; Kawagoshi, Y.; Baba, K.; Noma, Y.,
Determination of organic components in leachates from hazardous waste disposal sites in Japan by gas chromatography-mass spectrometry,
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Oda, Ichikawa, et al., 1996
Oda, J.; Ichikawa, S.; Mori, T.,
Analysis of polycyclic aromatic hydrocarbons in airborne particulates by capillary GC/MS method with programmed temperature relative retention index,
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Grung, Lichtenthaler, et al., 2007
Grung, M.; Lichtenthaler, R.; Ahel, M.; Tollefsen, K.-E.; Langford, K.; Thomas, K.V.,
Effects-directed analysis of organic toxicants in wastewater effluent from Zagreb, Croatia,
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Elizalde-González, Hutfliess, et al., 1996
Elizalde-González, M.P.; Hutfliess, M.; Hedden, K.,
Retention index system, adsorption characteristics, and sructure correlations of polycyclic aromatic hydrocarbons in fuels,
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Okumura, 1991
Okumura, T.,
retention indices of environmental chemicals on methyl silicone capillary column,
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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]
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,
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Chen, Keeran, et al., 2002
Chen, P.H.; Keeran, W.S.; Van Ausdale, W.A.; Schindler, D.R.; Roberts, D.W.,
Application of Lee retention indices to the confirmation of tentatively identified compounds from GC/MS analysis of environmental samples, Technical paper, Analytical Services Division, Environmental ScienceEngineering, Inc, PO Box 1703, Gainesville, FL 32602, 2002, 11. [all data]
Chen, 1996
Chen, J.,
GC and GC/MS methods for the analysis of polycyclic aromatic hydrocarbon (PAH) in sediment of the grand canal of China,
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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,
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Wise, Benner, et al., 1988
Wise, S.A.; Benner, B.A.; Byrd, G.D.; Chesler, S.N.; Rebbert, R.E.; Schantz, M.M.,
Determination of polycyclic aromatic hydrocarbons in a coal tar standard reference material,
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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,
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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,
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Wang, Li, et al., 2007
Wang, Z.; Li, K.; Lambert, P.; Yang, C.,
Identification, characterization and quantitation of pyrogenic polycylic aromatic hydrocarbons and other organic compounds in tire fire products,
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Wang, Li, et al., 2007, 2
Wang, Z.; Li, K.; Lambert, P.; Brown, C.E.; Yang, C.; Hollebone, B.P.,
Identification and characterization of polycyclic aromatic compounds in tire fire products and differentiation of pyrogenic PAHs from petrogenic PAHs
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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,
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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,
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Tucminen, Wickstrom, et al., 1986
Tucminen, A.; Wickstrom, K.; Pyysalo, H.,
Determination of Polycyclic Aromatic Compounds by GLC-Selected Ion Monitoring (SIM) Technique,
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. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), Gas Chromatography, References
- Symbols used in this document:
ΔfH°gas Enthalpy of formation of gas 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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