Azulene

• Formula: C₁₀H₈
• Molecular weight: 128.1705
• IUPAC Standard InChI: InChI=1S/C10H8/c1-2-5-9-7-4-8-10(9)6-3-1/h1-8H Copy

  
• IUPAC Standard InChIKey: CUFNKYGDVFVPHO-UHFFFAOYSA-N Copy
• CAS Registry Number: 275-51-4
• 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: Bicyclo[5.3.0]decapentaene; Cyclopentacycloheptene; Azunamic; Bicyclo(5.3.0)-1,3,5,7,9-decapentaene; Bicyclo(0.3.5)deca-1,3,5,7,9-pentaene; BICYCLO(5.3.0)-DECA-2,4,6,8,10-PENTAENE; Azusalen [as sodium sulfonate]
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• Information on this page:
  • Gas phase ion energetics data
  • Mass spectrum (electron ionization)
  • Gas Chromatography
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry data
  • Ion clustering data
  • IR Spectrum
  • UV/Visible spectrum
• Data at other public NIST sites:
  • Microwave spectra (on physics lab web site)
  • Gas Phase Kinetics Database
  • NIST Polycyclic Aromatic Hydrocarbon Structure Index
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Gas phase ion energetics data

Go To: Top, Mass spectrum (electron ionization), 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
MM - Michael M. Meot-Ner (Mautner)
LL - Sharon G. Lias and Joel F. Liebman
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
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 C₁₀H₈⁺ (ion structure unspecified)

Electron affinity determinations

Proton affinity at 298K

Gas basicity at 298K

Ionization energy determinations

Appearance energy determinations

De-protonation reactions

C₁₀H₇^- +  =

By formula: C₁₀H₇^- + H⁺ = C₁₀H₈

Mass spectrum (electron ionization)

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: NIST Mass Spectrometry Data Center, William E. Wallace, director

Spectrum

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Additional Data

Gas Chromatography

Go To: Top, Gas phase ion energetics data, Mass spectrum (electron ionization), 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

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Van Den Dool and Kratz RI, non-polar column, temperature ramp

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Van Den Dool and Kratz RI, polar column, temperature ramp

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Normal alkane RI, non-polar column, temperature ramp

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Normal alkane RI, polar column, temperature ramp

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Normal alkane RI, polar column, custom temperature program

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Lee's RI, non-polar column, temperature ramp

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References

Go To: Top, Gas phase ion energetics data, Mass spectrum (electron ionization), Gas Chromatography, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

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]

Schiedt, Knott, et al., 2000
Schiedt, J.; Knott, W.J.; Le Barbu, K.; Schlag, E.W.; Weinkauf, R., Microsolvation of similar-sized aromatic molecules: Photoelectron spectroscopy of bithiophene-, azulene-, and naphthalene-water anion clusters, J. Chem. Phys., 2000, 113, 21, 9470-9478, https://doi.org/10.1063/1.1319874 . [all data]

Chowdhury, Heinis, et al., 1986
Chowdhury, S.; Heinis, T.; Grimsrud, E.P.; Kebarle, P., Entropy Changes and Electron Affinities from Gas-Phase Electron Transfer Equilibria: A^- + B = A + B^-, J. Phys. Chem., 1986, 90, 12, 2747, https://doi.org/10.1021/j100403a037 . [all data]

Ando, Mitsui, et al., 2008
Ando, N.; Mitsui, M.; Nakajima, A., Photoelectron spectroscopy of cluster anions of naphthalene and related aromatic hydrocarbons, J. Chem. Phys., 2008, 128, 15, 154318, https://doi.org/10.1063/1.2903473 . [all data]

Chen, Chen, et al., 1992
Chen, E.C.M.; Chen, E.S.; Milligan, M.S.; Wentworth, W.E.; Wiley, J.R., Experimental Determination of the Electron Affinities of Nitrobenzene, Nitrotoluenes, Pentafluoronitrobenzene, and Isotopic Nitrobenzenes an, J. Phys. Chem., 1992, 96, 5, 2385, https://doi.org/10.1021/j100184a069 . [all data]

Grimsrud, Chowdhury, et al., 1985
Grimsrud, E.P.; Chowdhury, S.; Kebarle, P., Thermal energy electron detachment rate constants. The electron detachment from azulene- and the electron affinity of azulene, J. Chem. Phys., 1985, 83, 3983. [all data]

Becker and Chen, 1966
Becker, R.S.; Chen, E., Extension of Electron Affinities and Ionization Potentials of Aromatic Hydrocarbons, J. Chem. Phys., 1966, 45, 7, 2403, https://doi.org/10.1063/1.1727954 . [all data]

Wojnarovits and Foldiak, 1981
Wojnarovits, L.; Foldiak, G., Electron capture detection of aromatic hydrocarbons, J. Chromatogr. Sci., 1981, 206, 511. [all data]

Chen and Wentworth, 1989
Chen, E.C.M.; Wentworth, W.E., Experimental Determination of Electron Affinities of Organic Molecules, Mol. Cryst. Liq. Cryst., 1989, 171, 271. [all data]

Chaney, Christophorou, et al., 1970
Chaney, E.L.; Christophorou, L.G.; Collins, P.M.; Carter, J.C., Electron Attachment in the Field of the Ground and Excited States of the Azulene Molecule, J. Chem. Phys., 1970, 52, 9, 4413, https://doi.org/10.1063/1.1673666 . [all data]

Compton and Huebner, 1969
Compton, R.N.; Huebner, R.H., Temporary Attachment of Electrons to Azulene-h₈ and Azulene-d₈, J. Chem. Phys., 1969, 51, 7, 3132, https://doi.org/10.1063/1.1672468 . [all data]

Aue, Guidoni, et al., 2000
Aue, D.H.; Guidoni, M.; Betowski, L.D., Ab initio calculated gas-phase basicities of polynuclear aromatic hydrocarbons, Int. J. Mass Spectrom., 2000, 201, 283. [all data]

Jochims, Rasekh, et al., 1992
Jochims, H.-W.; Rasekh, H.; Ruhl, E.; Baumgartel, H.; Leach, S., The photofragmentation of naphthalene and azulene monocations in the energy range 7-22 eV, Chem. Phys., 1992, 168, 159. [all data]

Mautner(Meot-Ner), Nelsen, et al., 1984
Mautner(Meot-Ner), M.; Nelsen, S.F.; Willi, M.R.; Frigo, T.B., Special effects of an unusually large neutral to radical cation geometry change. Adiabatic ionization energies and proton affinities of alkylhydrazines, J. Am. Chem. Soc., 1984, 106, 7384. [all data]

Mautner(Meot-Ner), 1980
Mautner(Meot-Ner), M., Ion thermochemistry of low volatility compounds in the gas phase. 3. Polycyclic aromatics: Ionization energies, proton, and hydrogen affinities. Extrapolations to graphite, J. Phys. Chem., 1980, 84, 2716. [all data]

Boschi, Clar, et al., 1974
Boschi, R.; Clar, E.; Schmidt, W., Photoelectron spectra of polynuclear aromatics. III. The effect of nonplanarity in sterically overcrowded aromatic hydrocarbons, J. Chem. Phys., 1974, 60, 4406. [all data]

Dewar and Worley, 1969
Dewar, M.J.S.; Worley, S.D., Photoelectron spectra of molecules. I. Ionization potentials of some organic molecules and their interpretation, J. Chem. Phys., 1969, 50, 654. [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]

Kitagawa, Inokuchi, et al., 1966
Kitagawa, T.; Inokuchi, H.; Kodera, K., Photoionization of polycyclic aromatic compounds in vacuum ultraviolet region. Azulene, J.Mol. Spectry., 1966, 21, 267. [all data]

Kitagawa, Harada, et al., 1966
Kitagawa, T.; Harada, Y.; Inokuchi, H.; Kodera, K., Absorption spectrum of vapor phase azulene in vacuum ultraviolet region, J. Mol. Spectry., 1966, 19, 1. [all data]

Clark, 1965
Clark, L.B., Ionization potential of azulene, J. Chem. Phys., 1965, 43, 2566. [all data]

Finch, 1964
Finch, A.C.M., Charge-transfer spectra and the ionization energy of azulene, J. Chem. Soc., 1964, 2272. [all data]

Dougherty, Lewis, et al., 1980
Dougherty, D.; Lewis, J.; Nauman, R.V.; McGlynn, S.P., Photoelectron spectroscopy of azulenes, J. Electron Spectrosc. Relat. Phenom., 1980, 19, 21. [all data]

Heilbronner, Hoshi, et al., 1976
Heilbronner, E.; Hoshi, T.; von Rosenberg, J.L.; Hafner, K., Alkyl-induced, natural hypsochromic shifts of the ²A←²X and ²B←²X transitions of azulene and naphthalene radical cations, Nouv. J. Chim., 1976, 1, 105. [all data]

VanBrunt and Wacks, 1964
VanBrunt, R.J.; Wacks, M.E., Electron-impact studies of aromatic hydrocarbons. III. Azulene and naphthalene, J. Chem. Phys., 1964, 41, 3195. [all data]

Winters and Kiser, 1964
Winters, R.E.; Kiser, R.W., A mass spectrometric investigation of nickel tetracarbonyl and iron pentacarbonyl, Inorg. Chem., 1964, 3, 699. [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]

Dallos, Sisak, et al., 2000
Dallos, A.; Sisak, A.; Kulcsár, Z.; Kováts, E., Pair-wise interactions by gas chromatography VII. Interaction free enthalpies of solutes with secondary alcohol groups, J. Chromatogr. A, 2000, 904, 2, 211-242, https://doi.org/10.1016/S0021-9673(00)00908-0 . [all data]

Reddy, Dutoit, et al., 1992
Reddy, K.S.; Dutoit, J.-Cl.; Kovats, E. sz., Pair-wise interactions by gas chromatography. I. Interaction free enthalpies of solutes with non-associated primary alcohol groups, J. Chromatogr., 1992, 609, 1-2, 229-259, https://doi.org/10.1016/0021-9673(92)80167-S . [all data]

Engewald, Wennrich, et al., 1979
Engewald, W.; Wennrich, L.; Ritter, E., Molekülstruktur und Retentionsverhalten. XII. Zur Retention von Alkylnaphthalinen Bei der Gasverteilungs- und Gas-Adsorptions-Chromatographie, J. Chromatogr., 1979, 174, 2, 315-323, https://doi.org/10.1016/S0021-9673(00)86005-7 . [all data]

Rostad and Pereira, 1986
Rostad, C.E.; Pereira, W.E., Kovats and Lee retention indices determined by gas chromatography/mass spectrometry for organic compounds of environmental interest, J. Hi. Res. Chromatogr. Chromatogr. Comm., 1986, 9, 6, 328-334, https://doi.org/10.1002/jhrc.1240090603 . [all data]

Carugno and Rossi, 1967
Carugno, N.; Rossi, S., Evaluation of polynuclear hydrocarbons in cigarette smoke by glass capillary columns, J. Gas Chromatogr., 1967, 5, 2, 103-106, https://doi.org/10.1093/chromsci/5.2.103 . [all data]

Shimoda, Wu, et al., 1996
Shimoda, M.; Wu, Y.; Osajima, Y., Aroma compounds from aqueous solution of Haze (Rhus succedanea) honey determined by adsorptive column chromatography, J. Agric. Food Chem., 1996, 44, 12, 3913-3918, https://doi.org/10.1021/jf9601168 . [all data]

Nadim, Malik, et al., 2011
Nadim, M.M.; Malik, A.A.; Ahmad, J.; Bakshi, S.K., The essential oil composition of Achillea millefolium L. cultivated under tropical conditions in India, World J. Agricultural Sci., 2011, 7, 5, 561-565. [all data]

Piyachaiseth, Jirapakkul, et al., 2011
Piyachaiseth, T.; Jirapakkul, W.; Chaiseri, S., Aroma compounds of flash-fried rice, Kasetsart J. (Nat. Sci.), 2011, 45, 717-729. [all data]

Kaypak and Avsar, 2008
Kaypak, D.; Avsar, Y.K., Volatile and odor-active compounds of tuzlu yoghurt, Asian J. Chem., 2008, 20, 5, 3641-3648. [all data]

Lee and Kim, 2002
Lee, D.-S.; Kim, N.-S., Identification of fragrances from chestnut blossom by gas chromatography-ion trap mass spectrometry, Bull. Korean Chem. Soc., 2002, 23, 11, 1647-1650, https://doi.org/10.5012/bkcs.2002.23.11.1647 . [all data]

Vernin, 1991
Vernin, G., Volatile constituents of the essential oil of Santolina chamaecyparissus L., J. Essent. Oil Res., 1991, 3, 1, 49-53, https://doi.org/10.1080/10412905.1991.9697907 . [all data]

Lee, Vassilaros, et al., 1979
Lee, M.L.; Vassilaros, D.L.; White, C.M.; Novotny, M., Retention Indices for Programmed-Temperature Capillary-Column Gas Chromatography of Polycyclic Aromatic Hydrocarbons, Anal. Chem., 1979, 51, 6, 768-773, https://doi.org/10.1021/ac50042a043 . [all data]

Notes

Go To: Top, Gas phase ion energetics data, Mass spectrum (electron ionization), Gas Chromatography, References

• Symbols used in this document:
  

  AE	Appearance energy
  EA	Electron affinity
  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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