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, Phase change 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 |
Phase change data
Go To: Top, Condensed phase 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 compiled as indicated in comments:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
AC - William E. Acree, Jr., James S. Chickos
DH - Eugene S. Domalski and Elizabeth D. Hearing
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
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 511. ± 2. | K | AVG | N/A | Average of 18 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 256. ± 6. | K | AVG | N/A | Average of 19 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 258.360 | K | N/A | Steele, Archer, et al., 1988, 2 | Crystal phase 1 phase; Uncertainty assigned by TRC = 0.002 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 782.15 | K | N/A | Ambrose, 1963 | Uncertainty assigned by TRC = 3. K; TRC |
Tc | 800.15 | K | N/A | Glaser and Ruland, 1957 | Uncertainty assigned by TRC = 3. K; TRC |
Tc | 793.55 | K | N/A | Livingston, Morgan, et al., 1908 | Uncertainty assigned by TRC = 10. K; calculation based on extrap. of density and surface tension; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Pc | 57.04 | atm | N/A | Glaser and Ruland, 1957 | Uncertainty assigned by TRC = 3.0000 atm; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 14.18 ± 0.048 | kcal/mol | V | Steele, Archer, et al., 1988 | ALS |
ΔvapH° | 14.2 | kcal/mol | N/A | Steele, Archer, et al., 1988 | DRB |
ΔvapH° | 13.9 | kcal/mol | GS | Van de Rostyne and Prausnitz, 1980 | Based on data from 286. to 309. K.; AC |
ΔvapH° | 11.34 | kcal/mol | C | Glaser and Ruland, 1957 | ALS |
Reduced pressure boiling point
Tboil (K) | Pressure (atm) | Reference | Comment |
---|---|---|---|
387.2 | 0.022 | Weast and Grasselli, 1989 | BS |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
11.2 | 588. | DSC | Back, Grzyll, et al., 1996 | Based on data from 573. to 668. K.; AC |
11.1 | 519. | N/A | Lee, Chen, et al., 1992 | Based on data from 504. to 616. K.; AC |
13.8 ± 0.02 | 320. | IP,EB | Steele, Archer, et al., 1988 | Based on data from 298. to 559. K.; AC |
13.3 ± 0.02 | 360. | IP,EB | Steele, Archer, et al., 1988 | Based on data from 298. to 559. K.; AC |
12.7 ± 0.02 | 400. | IP,EB | Steele, Archer, et al., 1988 | Based on data from 298. to 559. K.; AC |
12.1 ± 0.02 | 440. | IP,EB | Steele, Archer, et al., 1988 | Based on data from 298. to 559. K.; AC |
11.6 ± 0.05 | 480. | IP,EB | Steele, Archer, et al., 1988 | Based on data from 298. to 559. K.; AC |
11.0 ± 0.07 | 520. | IP,EB | Steele, Archer, et al., 1988 | Based on data from 298. to 559. K.; AC |
11.0 | 478. | A | Stephenson and Malanowski, 1987 | Based on data from 463. to 794. K.; AC |
11.8 | 448. | EB | Stephenson and Malanowski, 1987 | Based on data from 433. to 511. K. See also Malanowski, 1961.; AC |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (atm)
T = temperature (K)
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Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
437.82 to 511.09 | 3.93472 | 1667.104 | -87.085 | Malanowski, 1961, 2 | Coefficents calculated by NIST from author's data. |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
2.5631 | 257.93 | Mastrangelo, 1957 | DH |
2.548 | 258.4 | Domalski and Hearing, 1996 | AC |
2.5810 | 258.4 | Parks, Todd, et al., 1936 | DH |
Entropy of fusion
ΔfusS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
9.988 | 258.4 | Parks, Todd, et al., 1936 | DH |
Entropy of fusion
ΔfusS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
0.074 | 220. | Domalski and Hearing, 1996 | CAL |
9.864 | 258.4 |
Temperature of phase transition
Ttrs (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|
220.093 | crystaline, II | crystaline, I | Steele, Chirico, et al., 1986 | DH |
258.369 | crystaline, I | liquid | Steele, Chirico, et al., 1986 | DH |
290. | liquid | liquid | Jalabert, Robert, et al., 1990 | DH |
Enthalpy of phase transition
ΔHtrs (kcal/mol) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
0.01630 | 220.000 | crystaline, II | crystaline, I | Steele, Archer, et al., 1988 | DH |
2.548495 | 258.369 | crystaline, I | liquid | Steele, Archer, et al., 1988 | DH |
Entropy of phase transition
ΔStrs (cal/mol*K) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
0.0741 | 220.000 | crystaline, II | crystaline, I | Steele, Archer, et al., 1988 | DH |
9.864 | 258.369 | crystaline, I | liquid | Steele, Archer, et al., 1988 | DH |
References
Go To: Top, Condensed phase thermochemistry data, Phase change 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]
Steele, Archer, et al., 1988, 2
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, 1233-64. [all data]
Ambrose, 1963
Ambrose, D.,
Critical Temperatures of Some Phenols and Other Organic Compounds,
Trans. Faraday Soc., 1963, 59, 1988. [all data]
Glaser and Ruland, 1957
Glaser, F.; Ruland, H.,
Untersuchungsen über dampfdruckkurven und kritische daten einiger technisch wichtiger organischer substanzen,
Chem. Ing. Techn., 1957, 29, 772. [all data]
Livingston, Morgan, et al., 1908
Livingston, J.; Morgan, R.; Higgins, E.,
The Weight of Falling Drops and Tate's Laws. Determination of Molecular Weights and Critical Temp. of Liquids Using Drop Weights: II.,
Z. Phys. Chem., Stoechiom. Verwandtschaftsl., 1908, 64, 170. [all data]
Van de Rostyne and Prausnitz, 1980
Van de Rostyne, Catherine; Prausnitz, John M.,
Vapor pressures of some nitrogen-containing, coal-derived liquids,
J. Chem. Eng. Data, 1980, 25, 1, 1-3, https://doi.org/10.1021/je60084a008
. [all data]
Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [all data]
Back, Grzyll, et al., 1996
Back, Dwight D.; Grzyll, Lawrence R.; Corrigan, Mary,
DSC enthalpy of vaporization measurements of high temperature two-phase working fluids,
Thermochimica Acta, 1996, 272, 53-63, https://doi.org/10.1016/0040-6031(95)02615-0
. [all data]
Lee, Chen, et al., 1992
Lee, Chang Ha; Chen, Quen; Mohamed, Rahoma S.; Holder, Gerald D.,
Vapor-liquid equilibria in the system of toluene/aniline, aniline/naphthalene, and naphthalene/quinoline,
J. Chem. Eng. Data, 1992, 37, 2, 179-183, https://doi.org/10.1021/je00006a011
. [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]
Malanowski, 1961
Malanowski, S.,
Bull. Acad. Pol. Sci. Ser. Sci. Chim., 1961, 9, 71. [all data]
Malanowski, 1961, 2
Malanowski, S.,
Vapour Pressures and Boiling Temperatures of Some Quinoline Bases,
Bull. Acad. Pol. Sci. Ser. Sci. Chim., 1961, 9, 2, 71-76. [all data]
Mastrangelo, 1957
Mastrangelo, S.V.R.,
Adiabatic calorimeter for determination of cryoscopic data,
Anal. Chem., 1957, 29(5), 841-845. [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]
Jalabert, Robert, et al., 1990
Jalabert, D.; Robert, J.B.; Roux-Buisson, H.,
Comportment anormal en temperature de la quinline liquide,
Calorim. Anal. Therm., 1990, 20-21, 441-447. [all data]
Notes
Go To: Top, Condensed phase thermochemistry data, Phase change data, References
- Symbols used in this document:
Cp,liquid Constant pressure heat capacity of liquid Pc Critical pressure S°liquid Entropy of liquid at standard conditions Tboil Boiling point Tc Critical temperature Tfus Fusion (melting) point Ttriple Triple point temperature Ttrs Temperature of phase transition ΔHtrs Enthalpy of phase transition ΔStrs Entropy of phase transition ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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