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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Condensed phase thermochemistry data
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 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°liquid | 33.75 ± 0.22 | kcal/mol | Ccr | Steele, Archer, et al., 1988 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -1119.3 ± 0.2 | kcal/mol | Ccr | Steele, Archer, et al., 1988 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°liquid | 52.514 | cal/mol*K | N/A | Steele, Archer, et al., 1988 | DH |
S°liquid | 52.507 | cal/mol*K | N/A | Steele, Chirico, et al., 1986 | DH |
S°liquid | 51.89 | cal/mol*K | N/A | Parks, Todd, et al., 1936 | Extrapolation below 90 K, 54.94 J/mol*K.; DH |
Constant pressure heat capacity of liquid
Cp,liquid (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
46.580 | 298.15 | Steele, Archer, et al., 1988 | T = 5 to 500 K.; DH |
46.582 | 298.15 | Steele, Chirico, et al., 1986 | T = 6 to 450 K.; DH |
48.71 | 298. | Tschamler and Krischai, 1951 | DH |
47.610 | 298.1 | Parks, Todd, et al., 1936 | T = 90 to 300 K.; DH |
46.10 | 302.5 | de Kolossowsky and Udowenko, 1934 | DH |
46.10 | 302.4 | Kolosovskii and Udovenko, 1934 | DH |
39.29 | 290. | Radulescu and Jula, 1934 | DH |
45.51 | 283. | Bramley, 1916 | Mean value, 0 to 20°C.; DH |
Reaction thermochemistry data
Go To: Top, Condensed phase 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: 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° | 385.6 ± 2.0 | kcal/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° | 376.9 ± 2.0 | kcal/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, Condensed phase thermochemistry data, Reaction thermochemistry data, 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) | 227.8 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 220.2 | kcal/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° | 385.6 ± 2.0 | kcal/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° | 376.9 ± 2.0 | kcal/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 |
References
Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Steele, Archer, et al., 1988
Steele, W.V.; Archer, D.G.; Chirico, R.D.; Collier, W.B.; Hossenlopp, I.A.; Nguyen, A.; Smith, N.K.; Gammon, B.E.,
The thermodynamic properties of quinoline and isoquinoline,
J. Chem. Thermodyn., 1988, 20, 1233-1264. [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]
Parks, Todd, et al., 1936
Parks, G.S.; Todd, S.S.; Moore, W.A.,
Thermal data on organic compounds. XVI. Some heat capacity, entropy and free energy data for typical benzene derivatives and heterocyclic compounds,
J. Am. Chem. Soc., 1936, 58, 398-401. [all data]
Tschamler and Krischai, 1951
Tschamler, H.; Krischai, H.,
Chinolin-m-Kresol, ein stark negatives System,
Monatsh. Chem., 1951, 82, 259-270. [all data]
de Kolossowsky and Udowenko, 1934
de Kolossowsky, N.; Udowenko, W.W.,
Determination des chaleurs specifiques des liquides,
Compt. rend., 1934, 198, 1394-1395. [all data]
Kolosovskii and Udovenko, 1934
Kolosovskii, N.A.; Udovenko, W.W.,
Specific heat of liquids. II.,
Zhur. Obshchei Khim., 1934, 4, 1027-1033. [all data]
Radulescu and Jula, 1934
Radulescu, D.; Jula, O.,
Beiträge zur Bestimmung der Abstufung der Polarität des Aminstickstoffes in den organischen Verbindungen,
Z. Phys. Chem., 1934, B26, 390-393. [all data]
Bramley, 1916
Bramley, A.,
The study of binary mixtures. Part IV. Heats of reaction and specific heats,
J. Chem. Soc. (London), 1916, 109, 496-515. [all data]
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,
J. Phys. Chem. A, 1997, 101, 38, 7061, https://doi.org/10.1021/jp970211z
. [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]
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,
Tetrahedron Lett., 1973, 3743. [all data]
Brogli, Heilbronner, et al., 1972
Brogli, F.; Heilbronner, E.; Kobayashi, T.,
Photoelectron spectra of azabenzenes and azanaphthalenes: II. A reinvestigation of azanaphthalenes by high-resolution photoelectron spectroscopy,
Helv. Chim. Acta, 1972, 55, 274. [all data]
Dewar and Worley, 1969
Dewar, M.J.S.; Worley, S.D.,
Photoelectron spectra of molecules. II.The ionization potentials of azabenzenes and azanaphthalenes,
J. Chem. Phys., 1969, 51, 263. [all data]
Eland and Danby, 1968
Eland, J.H.D.; Danby, C.J.,
Inner ionization potentials of aromatic compounds,
Z. Naturforsch., 1968, 23a, 355. [all data]
Terenin, 1961
Terenin, A.,
Charge transfer in organic solids, induced by light,
Proc. Chem. Soc., London, 1961, 321. [all data]
Van Den Ham and Van Der Meer, 1972
Van Den Ham, D.M.W.; Van Der Meer, D.,
Perfluoro effect in the photoelectron spectra of quinoline and isoquinoline,
Chem. Phys. Lett., 1972, 15, 549. [all data]
Notes
Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, References
- Symbols used in this document:
Cp,liquid Constant pressure heat capacity of liquid IE (evaluated) Recommended ionization energy S°liquid Entropy of liquid at standard conditions ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°liquid Enthalpy of formation of liquid 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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