Quinoline

Data at NIST subscription sites:

NIST subscription sites provide data under the NIST Standard Reference Data Program, but require an annual fee to access. The purpose of the fee is to recover costs associated with the development of data collections included in such sites. Your institution may already be a subscriber. Follow the links above to find out more about the data in these sites and their terms of usage.


Phase change data

Go To: Top, 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:
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
Tboil511. ± 2.KAVGN/AAverage of 18 values; Individual data points
Quantity Value Units Method Reference Comment
Tfus256. ± 6.KAVGN/AAverage of 19 values; Individual data points
Quantity Value Units Method Reference Comment
Ttriple258.360KN/ASteele, Archer, et al., 1988Crystal phase 1 phase; Uncertainty assigned by TRC = 0.002 K; TRC
Quantity Value Units Method Reference Comment
Tc782.15KN/AAmbrose, 1963Uncertainty assigned by TRC = 3. K; TRC
Tc800.15KN/AGlaser and Ruland, 1957Uncertainty assigned by TRC = 3. K; TRC
Tc793.55KN/ALivingston, Morgan, et al., 1908Uncertainty assigned by TRC = 10. K; calculation based on extrap. of density and surface tension; TRC
Quantity Value Units Method Reference Comment
Pc57.04atmN/AGlaser and Ruland, 1957Uncertainty assigned by TRC = 3.0000 atm; TRC
Quantity Value Units Method Reference Comment
Δvap14.18 ± 0.048kcal/molVSteele, Archer, et al., 1988, 2ALS
Δvap14.2kcal/molN/ASteele, Archer, et al., 1988, 2DRB
Δvap13.9kcal/molGSVan de Rostyne and Prausnitz, 1980Based on data from 286. to 309. K.; AC
Δvap11.34kcal/molCGlaser and Ruland, 1957ALS

Reduced pressure boiling point

Tboil (K) Pressure (atm) Reference Comment
387.20.022Weast and Grasselli, 1989BS

Enthalpy of vaporization

ΔvapH (kcal/mol) Temperature (K) Method Reference Comment
11.2588.DSCBack, Grzyll, et al., 1996Based on data from 573. to 668. K.; AC
11.1519.N/ALee, Chen, et al., 1992Based on data from 504. to 616. K.; AC
13.8 ± 0.02320.IP,EBSteele, Archer, et al., 1988, 2Based on data from 298. to 559. K.; AC
13.3 ± 0.02360.IP,EBSteele, Archer, et al., 1988, 2Based on data from 298. to 559. K.; AC
12.7 ± 0.02400.IP,EBSteele, Archer, et al., 1988, 2Based on data from 298. to 559. K.; AC
12.1 ± 0.02440.IP,EBSteele, Archer, et al., 1988, 2Based on data from 298. to 559. K.; AC
11.6 ± 0.05480.IP,EBSteele, Archer, et al., 1988, 2Based on data from 298. to 559. K.; AC
11.0 ± 0.07520.IP,EBSteele, Archer, et al., 1988, 2Based on data from 298. to 559. K.; AC
11.0478.AStephenson and Malanowski, 1987Based on data from 463. to 794. K.; AC
11.8448.EBStephenson and Malanowski, 1987Based 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)

View plot Requires a JavaScript / HTML 5 canvas capable browser.

Temperature (K) A B C Reference Comment
437.82 to 511.093.934721667.104-87.085Malanowski, 1961, 2Coefficents calculated by NIST from author's data.

Enthalpy of fusion

ΔfusH (kcal/mol) Temperature (K) Reference Comment
2.5631257.93Mastrangelo, 1957DH
2.548258.4Domalski and Hearing, 1996AC
2.5810258.4Parks, Todd, et al., 1936DH

Entropy of fusion

ΔfusS (cal/mol*K) Temperature (K) Reference Comment
9.988258.4Parks, Todd, et al., 1936DH

Entropy of fusion

ΔfusS (cal/mol*K) Temperature (K) Reference Comment
0.074220.Domalski and Hearing, 1996CAL
9.864258.4

Temperature of phase transition

Ttrs (K) Initial Phase Final Phase Reference Comment
220.093crystaline, IIcrystaline, ISteele, Chirico, et al., 1986DH
258.369crystaline, IliquidSteele, Chirico, et al., 1986DH
290.liquidliquidJalabert, Robert, et al., 1990DH

Enthalpy of phase transition

ΔHtrs (kcal/mol) Temperature (K) Initial Phase Final Phase Reference Comment
0.01630220.000crystaline, IIcrystaline, ISteele, Archer, et al., 1988, 2DH
2.548495258.369crystaline, IliquidSteele, Archer, et al., 1988, 2DH

Entropy of phase transition

ΔStrs (cal/mol*K) Temperature (K) Initial Phase Final Phase Reference Comment
0.0741220.000crystaline, IIcrystaline, ISteele, Archer, et al., 1988, 2DH
9.864258.369crystaline, IliquidSteele, Archer, et al., 1988, 2DH

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:


Gas phase ion energetics 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 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 ± 0.02eVN/AN/AL
Quantity Value Units Method Reference Comment
Proton affinity (review)227.8kcal/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity220.2kcal/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
8.62PESchafer, Schweig, et al., 1973LLK
8.62PEBrogli, Heilbronner, et al., 1972LLK
8.62PEDewar and Worley, 1969RDSH
8.67 ± 0.05PEEland and Danby, 1968RDSH
8.3PITerenin, 1961RDSH
8.62PEVan Den Ham and Van Der Meer, 1972Vertical value; LLK

De-protonation reactions

quinolinide anion + Hydrogen cation = Quinoline

By formula: C9H6N- + H+ = C9H7N

Quantity Value Units Method Reference Comment
Δr385.6 ± 2.0kcal/molTDEqMeot-ner, Liebman, et al., 1988gas 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
Δr376.9 ± 2.0kcal/molTDEqMeot-ner, Liebman, et al., 1988gas 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, Phase change 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, 1233-64. [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]

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, 1233-1264. [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]

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]

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]

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]

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]

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]


Notes

Go To: Top, Phase change data, Gas phase ion energetics data, References