Isoquinoline

• Formula: C₉H₇N
• Molecular weight: 129.1586
• IUPAC Standard InChI: InChI=1S/C9H7N/c1-2-4-9-7-10-6-5-8(9)3-1/h1-7H Copy

  
• IUPAC Standard InChIKey: AWJUIBRHMBBTKR-UHFFFAOYSA-N Copy
• CAS Registry Number: 119-65-3
• 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: β-Quinoline; Benzopyridine; Benzo[c]pyridine; Leucoline; 2-Azanaphthalene; 2-Benzazine; 2-Benzanine; Isochinolin; NSC 3395
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Gas phase thermochemistry data
  • Phase change data
  • Gas phase ion energetics data
  • References
  • Notes
• Other data available:
  • Condensed phase thermochemistry data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
  • Gas Chromatography
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
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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.

Phase change 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:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
DRB - Donald R. Burgess, Jr.
AC - William E. Acree, Jr., James S. Chickos
DH - Eugene S. Domalski and Elizabeth D. Hearing

Reduced pressure boiling point

Enthalpy of vaporization

Antoine Equation Parameters

log₁₀(P) = A − (B / (T + C))
    P = vapor pressure (bar)
    T = temperature (K)

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Enthalpy of fusion

Temperature of phase transition

Enthalpy of phase transition

Entropy of phase transition

Gas phase ion energetics 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 evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias
L - Sharon G. Lias

Data compiled as indicated in comments:
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)

Ionization energy determinations

References

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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]

Good, 1972
Good, W.D., Enthalpies of combustion of nine organic nitrogen compounds related to petroleum, J. Chem. Eng. Data, 1972, 17, 28-31. [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]

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]

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]

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]

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]

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., 1975
Schafer, W.; Schweig, A.; Vermeer, H.; Bickel-haupt, F.; De Graaf, H., On the nature of the "free electron pair" on phosphorus in aromatic phosphorus compounds: the photoelectron spectrum of 2-phosphanaphthalene, J. Electron Spectrosc. Relat. Phenom., 1975, 6, 91. [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]

Yencha and El-Sayed, 1968
Yencha, A.J.; El-Sayed, M.A., Lowest ionization potentials of some nitrogen heterocyclics, J. Chem. Phys., 1968, 48, 3469. [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]

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

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• Symbols used in this document:
  

  IE (evaluated)	Recommended ionization energy
  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
  ΔfH°gas	Enthalpy of formation of gas at standard conditions
  ΔfusH	Enthalpy 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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