Quinoline
- Formula: C9H7N
- Molecular weight: 129.1586
- IUPAC Standard InChIKey: SMWDFEZZVXVKRB-UHFFFAOYSA-N
- CAS Registry Number: 91-22-5
- 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: B 500; Benzopyridine; Benzo[b]Pyridine; Leucol; Leukol; Quinolin; 1-Azanaphthalene; 1-Benzazine; Chinoline; Chinoleine; Chinolin; Leucoline; USAF EK-218; UN 2656; NSC 3396
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Reaction thermochemistry data
Go To: Top, Gas phase ion energetics data, 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
By formula: C9H6N- + H+ = C9H7N
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1613. ± 8.4 | kJ/mol | TDEq | Meot-ner, Liebman, et al., 1988 | gas phase; anchored to 88MEO scale, not the "87 acidity scale". The Kiefer, Zhang, et al., 1997 BDE is for ortho. |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1577. ± 8.4 | kJ/mol | TDEq | Meot-ner, Liebman, et al., 1988 | gas phase; anchored to 88MEO scale, not the "87 acidity scale". The Kiefer, Zhang, et al., 1997 BDE is for ortho. |
Gas phase ion energetics data
Go To: Top, Reaction thermochemistry data, 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 evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias
L - Sharon G. Lias
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 C9H7N+ (ion structure unspecified)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
IE (evaluated) | 8.63 ± 0.02 | eV | N/A | N/A | L |
Quantity | Value | Units | Method | Reference | Comment |
Proton affinity (review) | 953.2 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 921.4 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
8.62 | PE | Schafer, Schweig, et al., 1973 | LLK |
8.62 | PE | Brogli, Heilbronner, et al., 1972 | LLK |
8.62 | PE | Dewar and Worley, 1969 | RDSH |
8.67 ± 0.05 | PE | Eland and Danby, 1968 | RDSH |
8.3 | PI | Terenin, 1961 | RDSH |
8.62 | PE | Van Den Ham and Van Der Meer, 1972 | Vertical value; LLK |
De-protonation reactions
By formula: C9H6N- + H+ = C9H7N
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1613. ± 8.4 | kJ/mol | TDEq | Meot-ner, Liebman, et al., 1988 | gas phase; anchored to 88MEO scale, not the "87 acidity scale". The Kiefer, Zhang, et al., 1997 BDE is for ortho.; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1577. ± 8.4 | kJ/mol | TDEq | Meot-ner, Liebman, et al., 1988 | gas phase; anchored to 88MEO scale, not the "87 acidity scale". The Kiefer, Zhang, et al., 1997 BDE is for ortho.; B |
Gas Chromatography
Go To: Top, Reaction thermochemistry data, 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 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-101 | 140. | 1231. | Dmitrikov and Nabivach, 1995 | He |
Capillary | OV-101 | 160. | 1246. | Dmitrikov and Nabivach, 1995 | He |
Capillary | HP-1 | 100. | 1206. | Zhang, Li, et al., 1992 | N2; Column length: 25. m; Column diameter: 0.20 mm |
Capillary | HP-1 | 100. | 1207. | Zhang, Li, et al., 1992 | N2; Column length: 25. m; Column diameter: 0.20 mm |
Capillary | OV-101 | 140. | 1231. | Berlizov, Nabivach, et al., 1987 | N2; Column length: 50. m; Column diameter: 0.22 mm |
Capillary | OV-101 | 160. | 1246. | Berlizov, Nabivach, et al., 1987 | N2; Column length: 50. m; Column diameter: 0.22 mm |
Capillary | OV-101 | 140. | 1226. | Berlizov, Berezkin, et al., 1986 | N2; Column length: 15. m; Column diameter: 0.20 mm |
Capillary | OV-101 | 140. | 1226. | Berlizov, Berezkin, et al., 1986 | N2; Column length: 15. m; Column diameter: 0.20 mm |
Capillary | OV-101 | 140. | 1227. | Berlizov, Berezkin, et al., 1986 | N2; Column length: 15. m; Column diameter: 0.20 mm |
Capillary | OV-101 | 140. | 1231. | Berlizov, Berezkin, et al., 1986 | N2; Column length: 15. m; Column diameter: 0.20 mm |
Capillary | OV-101 | 140. | 1233. | Berlizov, Berezkin, et al., 1986 | N2; Column length: 15. m; Column diameter: 0.20 mm |
Capillary | OV-101 | 150. | 1228. | Morishita, Morimoto, et al., 1986 | N2; Column length: 20. m; Column diameter: 0.23 mm |
Capillary | OV-101 | 140. | 1247.7 | 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 | 1247. | Ramsey, Lee, et al., 1980 | He, Chromosorb G HP (80-100 mesh); Column length: 1.5 m; Program: not specified |
Kovats' RI, polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Packed | Carbowax 20M | 160. | 1892. | Kurbatova, Finkelstein, et al., 2004 | Chromaton N-AW; Column length: 1. m |
Capillary | PEG-20M | 140. | 1897. | Dmitrikov and Nabivach, 1995 | He |
Capillary | PEG-20M | 160. | 1924. | Dmitrikov and Nabivach, 1995 | He |
Capillary | PEG-20M | 140. | 1897. | Berlizov, Nabivach, et al., 1987 | N2; Column length: 30. m; Column diameter: 0.25 mm |
Capillary | PEG-20M | 160. | 1924. | Berlizov, Nabivach, et al., 1987 | N2; Column length: 30. m; Column diameter: 0.25 mm |
Capillary | PEG-20M | 140. | 1897. | Buryan, Macák, et al., 1987 | N2; Column length: 30. m; Column diameter: 0.25 mm |
Capillary | PEG-20M | 160. | 1924. | Buryan, Macák, et al., 1987 | N2; Column length: 30. m; Column diameter: 0.25 mm |
Capillary | PEG-20M | 150. | 1920. | Morishita, Morimoto, et al., 1986 | N2; Column length: 20. m; Column diameter: 0.23 mm |
Van Den Dool and Kratz RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-5 | 1224.7 | Song, Lai, et al., 2003 | 30. m/0.25 mm/0.25 μm, He, 2. K/min; Tstart: 40. C; Tend: 310. C |
Capillary | DB-5 | 1233.0 | Song, Lai, et al., 2003 | 30. m/0.25 mm/0.25 μm, He, 4. K/min; Tstart: 40. C; Tend: 310. C |
Capillary | DB-5 | 1237.4 | Song, Lai, et al., 2003 | 30. m/0.25 mm/0.25 μm, He, 6. K/min; Tstart: 40. C; Tend: 310. C |
Capillary | OV-1 | 1203.7 | Gautzsch and Zinn, 1996 | 8. K/min; Tstart: 35. C; Tend: 300. C |
Capillary | DB-5 | 1224.7 | Lai and Song, 1995 | 30. m/0.25 mm/0.25 μm, He, 2. K/min; Tstart: 40. C; Tend: 310. C |
Capillary | DB-5 | 1233. | Lai and Song, 1995 | 30. m/0.25 mm/0.25 μm, He, 4. K/min; Tstart: 40. C; Tend: 310. C |
Capillary | DB-5 | 1237.4 | Lai and Song, 1995 | 30. m/0.25 mm/0.25 μm, He, 6. K/min; Tstart: 40. C; Tend: 310. C |
Capillary | DB-5 | 1239. | Rostad and Pereira, 1986 | 30. m/0.26 mm/0.25 μm, He, 50. C @ 4. min, 6. K/min, 300. C @ 20. min |
Van Den Dool and Kratz RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | 5 % Phenyl methyl siloxane | 1230. | Yasuhara, Shiraishi, et al., 1997 | 25. m/0.31 mm/0.52 μm, He; Program: 50C(2min) => (20C/min) => 120C => (7C/min) => 310C(10min) |
Normal alkane RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Ultra-1 | 1200. | Du, Clery, et al., 2008 | 50. m/0.20 mm/0.33 μm, Helium, 2. K/min, 280. C @ 20. min; Tstart: 50. C |
Capillary | HP-5 | 1242. | Du, Clery, et al., 2008 | 50. m/0.20 mm/0.33 μm, Helium, 10. K/min, 280. C @ 8.5 min; Tstart: 50. C |
Capillary | HP-5 | 1240.3 | Leffingwell and Alford, 2005 | 60. m/0.32 mm/0.25 μm, He, 30. C @ 2. min, 2. K/min, 260. C @ 28. min |
Capillary | ZB-5 | 1224. | Kluchinsky, Sheely, et al., 2002 | 30. m/0.25 mm/0.25 μm, He, 10. K/min, 200. C @ 2. min; Tstart: 40. C |
Capillary | SE-30 | 1221.6 | Bur'yan and Nabivach, 1992 | 1.7 K/min; Tstart: 82. C; Tend: 177. C |
Capillary | SE-30 | 1221.6 | Bur'yan and Nabivach, 1992 | 1.7 K/min; Tstart: 82. C; Tend: 177. C |
Capillary | DB-1 | 1201. | Ishihara, Tsuneya, et al., 1992 | 60. m/0.25 mm/0.25 μm, He, 50. C @ 5. min, 3. K/min; Tend: 240. C |
Capillary | DB-1 | 1206. | Ishihara, Tsuneya, et al., 1992 | 60. m/0.25 mm/0.25 μm, He, 50. C @ 5. min, 3. K/min; Tend: 240. C |
Capillary | Ultra-1 | 1199. | Okumura, 1991 | 25. m/0.32 mm/0.25 μm, He, 3. K/min; Tstart: 80. C; Tend: 260. C |
Capillary | DB-1 | 1199. | Flath, Matsumoto, et al., 1989 | 60. m/0.32 mm/0.25 μm, 4. K/min; Tstart: 50. C; Tend: 250. C |
Capillary | DB-1 | 1200. | Flath, Matsumoto, et al., 1989 | 60. m/0.32 mm/0.25 μm, 4. K/min; Tstart: 50. C; Tend: 250. C |
Capillary | SE-30 | 1203. | Ibrahim and Suffet, 1988 | N2, 50. C @ 8. min, 5. K/min, 275. C @ 10. min; Column length: 60. m; Column diameter: 0.32 mm |
Normal alkane RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Polydimethyl siloxane, unknown content of Ph-groups | 1238. | Geldon, 1989 | Program: not specified |
Capillary | Polydimethyl siloxane, unknown content of Ph-groups | 1242. | Geldon, 1989 | Program: not specified |
Capillary | SE-30 | 1205. | Ibrahim and Suffet, 1988 | N2; Column length: 60. m; Column diameter: 0.32 mm; Program: 50C(8min) => 3C/min => 150C => 35C/min => 275C (10min) |
Capillary | OV-1, SE-30, Methyl silicone, SP-2100, OV-101, DB-1, etc. | 1247. | Waggott and Davies, 1984 | Hydrogen; Column length: 50. m; Column diameter: 0.32 mm; Program: not specified |
Other | Methyl Silicone | 1247. | Ardrey and Moffat, 1981 | Program: not specified |
Normal alkane RI, polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | HP-Innowax | 1903. | Du, Clery, et al., 2008 | 50. m/0.20 mm/0.33 μm, Helium, 10. K/min, 250. C @ 6. min; Tstart: 50. C |
Normal alkane RI, polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-Wax | 1942. | Peng, Yang, et al., 1991 | Program: not specified |
Lee's RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | HP-5 | 210.7 | Wang, Hou, et al., 2007 | 30. m/0.30 mm/0.25 μm, Helium, 50. C @ 5. min, 5. K/min, 200. C @ 15. min |
Capillary | DB-5MS | 210.37 | 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-5 | 206.0 | Durlak, Biswas, et al., 1998 | 30. m/0.25 mm/0.25 μm, 15. K/min; Tstart: 50. C; Tend: 300. C |
Capillary | SE-52 | 210.18 | 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 | 209.51 | 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 | 210.32 | 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 | 210.26 | 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 | 209.70 | 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 | SE-54 | 210.17 | Guillen, Iglesias, et al., 1992 | Program: not specified |
Capillary | SE-52 | 210.26 | Hasegawa, Usami, et al., 1990 | Column length: 12. m; Column diameter: 0.25 mm; Program: not specified |
References
Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, Gas Chromatography, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Meot-ner, Liebman, et al., 1988
Meot-ner, M.; Liebman, J.F.; Kafafi, S.A.,
Ionic Probes of Aromaticity in Annelated Rings,
J. Am. Chem. Soc., 1988, 110, 18, 5937, https://doi.org/10.1021/ja00226a001
. [all data]
Kiefer, Zhang, et al., 1997
Kiefer, J.H.; Zhang, Q.; Kern, R.D.; Yao, J.; Jursic, B.,
Pyrolysis of Aromatic Azines: Pyrazine, Pyrimidine, and Pyridine,
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Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G.,
Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update,
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Schafer, Schweig, et al., 1973
Schafer, W.; Schweig, A.; Markl, G.; Heier, K.-H.,
Zur elektronenstruktur der lambda3- und lambda5-phosphanaphthaline--ungewohnlich grosse MO destabilisierungen,
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Dewar, M.J.S.; Worley, S.D.,
Photoelectron spectra of molecules. II.The ionization potentials of azabenzenes and azanaphthalenes,
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Inner ionization potentials of aromatic compounds,
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Charge transfer in organic solids, induced by light,
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Van Den Ham and Van Der Meer, 1972
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Perfluoro effect in the photoelectron spectra of quinoline and isoquinoline,
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Physico-chemical regularities of quinoline bases retention in gas chromatography,
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Zhang, M.J.; Li, S.D.; Chen, B.J.,
Compositional studies of high-temperature coal tar by GC/FTIR analysis of light oil fractions,
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Capillary gas chromatography of alkylquinolines,
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Investigation of chromatographic properties of gass and quartz capillary columns,
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Prediction of molecular structures of aza-arenes by retention indices and fluorescence spectra,
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Kovats and Lee retention indices determined by gas chromatography/mass spectrometry for organic compounds of environmental interest,
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Freon FC-113, an Alternative to Methylene Chloride for Liquid-Liquid Extraction of Trace Organics from Chlorinated Drinking Water,
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Notes
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- Symbols used in this document:
IE (evaluated) Recommended ionization energy 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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