Azulene

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Condensed 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity Value Units Method Reference Comment
Δcliquid-5293. ± 3.kJ/molCcbQuitzsch, Schaffernicht, et al., 1963Corresponding Δfliquid = 215. kJ/mol (simple calculation by NIST; no Washburn corrections)
Quantity Value Units Method Reference Comment
Δfsolid212.kJ/molCcbKovats, Gunthard, et al., 1957Correction to Kovats, Gunthard, et al., 1955
Quantity Value Units Method Reference Comment
Δcsolid-5290.7kJ/molCcbKovats, Gunthard, et al., 1957Correction to Kovats, Gunthard, et al., 1955; Corresponding Δfsolid = 212. kJ/mol (simple calculation by NIST; no Washburn corrections)

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
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.

Quantity Value Units Method Reference Comment
Tboil515.2KN/AAldrich Chemical Company Inc., 1990BS
Quantity Value Units Method Reference Comment
Tfus373.KN/ATurner, Meador, et al., 1957Uncertainty assigned by TRC = 2. K; TRC
Tfus303.65KN/ABirrrell, 1935Uncertainty assigned by TRC = 1. K; TRC
Quantity Value Units Method Reference Comment
Δvap52.8kJ/molCGCChickos, Hesse, et al., 1998AC
Δvap63.8 ± 0.2kJ/molVBauder and Gunthard, 1962ALS
Quantity Value Units Method Reference Comment
Δsub80. ± 20.kJ/molAVGN/AAverage of 7 values; Individual data points

Enthalpy of vaporization

ΔvapH (kJ/mol) Temperature (K) Method Reference Comment
53.0384.AStephenson and Malanowski, 1987Based on data from 369. to 515. K.; AC
51.2457.EBMeyer and Gens, 1977Based on data from 442. to 534. K.; AC
55.5373.N/ABauder and G«65533»nthard, 1962Based on data from 373. to 423. K.; AC

Enthalpy of sublimation

ΔsubH (kJ/mol) Temperature (K) Method Reference Comment
78.4 ± 1.3303.HSAChickos, Hesse, et al., 1998Based on data from 283. to 326. K.; AC
82.8305.SStephenson and Malanowski, 1987Based on data from 290. to 372. K.; AC
75.8273.N/AHoyer and Peperle, 1958Based on data from 253. to 293. K.; AC

Enthalpy of fusion

ΔfusH (kJ/mol) Temperature (K) Method Reference Comment
17.53373.5DSCChickos, Hesse, et al., 1998AC

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

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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:
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)

Quantity Value Units Method Reference Comment
IE (evaluated)7.42 ± 0.02eVN/AN/AL
Quantity Value Units Method Reference Comment
Proton affinity (review)925.2kJ/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity896.kJ/molN/AHunter and Lias, 1998HL

Electron affinity determinations

EA (eV) Method Reference Comment
0.7900 ± 0.0080LPESSchiedt, Knott, et al., 2000B
0.69 ± 0.10TDEqChowdhury, Heinis, et al., 1986ΔGea(423 K) = -18.0 kcal/mol; ΔSea = +4.5 eu.; B
0.80 ± 0.10LPESAndo, Mitsui, et al., 2008Stated electron affinity is the Vertical Detachment Energy; B
0.690 ± 0.040ECDChen, Chen, et al., 1992B
0.681 ± 0.043KineGrimsrud, Chowdhury, et al., 1985B
0.6560 ± 0.0080ECDBecker and Chen, 1966B
<0.520 ± 0.013ECDWojnarovits and Foldiak, 1981EA is an upper limit: Chen and Wentworth, 1989. G3MP2B3 calculations indicate an EA of ca. 0.6 eV.; B
>0.460008ESChaney, Christophorou, et al., 1970Lifetime: Compton and Huebner, 1969; B

Proton affinity at 298K

Proton affinity (kJ/mol) Reference Comment
927.6Aue, Guidoni, et al., 2000Experimental literature data re-evaluated by the authors using ab initio protonation entropies; MM

Gas basicity at 298K

Gas basicity (review) (kJ/mol) Reference Comment
896.6Aue, Guidoni, et al., 2000Experimental literature data re-evaluated by the authors using ab initio protonation entropies; MM

Ionization energy determinations

IE (eV) Method Reference Comment
7.38 ± 0.03PIJochims, Rasekh, et al., 1992LL
7.32 ± 0.05EQMautner(Meot-Ner), Nelsen, et al., 1984LBLHLM
7.41 ± 0.05EQMautner(Meot-Ner), 1980LLK
7.43 ± 0.04PEBoschi, Clar, et al., 1974LLK
7.43 ± 0.01PEDewar and Worley, 1969RDSH
7.42 ± 0.05PEEland and Danby, 1968RDSH
7.41PIKitagawa, Inokuchi, et al., 1966RDSH
7.408SKitagawa, Harada, et al., 1966RDSH
7.431 ± 0.006SClark, 1965RDSH
7.4CTSFinch, 1964RDSH
7.42PEDougherty, Lewis, et al., 1980Vertical value; LLK
7.44 ± 0.03PEHeilbronner, Hoshi, et al., 1976Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C4H3+20.90 ± 0.102C2H2+C2HPIJochims, Rasekh, et al., 1992LL
C4H4+19.1 ± 0.1C4H2+C2H2PIJochims, Rasekh, et al., 1992LL
C4H4+17.8 ± 0.10?EIVanBrunt and Wacks, 1964RDSH
C5H3+18.5 ± 0.1C3H3+C2H2PIJochims, Rasekh, et al., 1992LL
C5H4+19.63 ± 0.15C3H3+C2HPIJochims, Rasekh, et al., 1992LL
C6H3+19.2 ± 0.15?EIVanBrunt and Wacks, 1964RDSH
C6H4+17.30 ± 0.052C2H2PIJochims, Rasekh, et al., 1992LL
C6H4+16.7 ± 0.15?EIVanBrunt and Wacks, 1964RDSH
C6H5+17.21 ± 0.05C2H2+C2HPIJochims, Rasekh, et al., 1992LL
C6H5+16.9 ± 0.10?EI2Winters and Kiser, 1964RDSH
C6H6+14.25 ± 0.05C4H2PIJochims, Rasekh, et al., 1992LL
C6H6+13.86 ± 0.05?EIVanBrunt and Wacks, 1964RDSH
C8H5+17.7 ± 0.1C2H2+HPIJochims, Rasekh, et al., 1992LL
C8H5+16.3 ± 0.15?EIVanBrunt and Wacks, 1964RDSH
C8H6+13.96 ± 0.05C2H2PIJochims, Rasekh, et al., 1992LL
C8H6+13.6 ± 0.10C2H2EIVanBrunt and Wacks, 1964RDSH
C10H6+14.2 ± 0.1H2PIJochims, Rasekh, et al., 1992LL
C10H6+14.7 ± 0.10H2EIVanBrunt and Wacks, 1964RDSH
C10H7+14.0 ± 0.1HPIJochims, Rasekh, et al., 1992LL
C10H7+14.0 ± 0.10HEIVanBrunt and Wacks, 1964RDSH

De-protonation reactions

C10H7- + Hydrogen cation = Azulene

By formula: C10H7- + H+ = C10H8

Quantity Value Units Method Reference Comment
Δr1538. ± 10.kJ/molTDEqMeot-ner, Liebman, et al., 1988gas phase; Acidity seriously disagrees with high level calculations. Dissociative to acetylide? C-3is most acidic site by G3MP2B3 calns.; B
Quantity Value Units Method Reference Comment
Δr1507. ± 8.4kJ/molTDEqMeot-ner, Liebman, et al., 1988gas phase; Acidity seriously disagrees with high level calculations. Dissociative to acetylide? C-3is most acidic site by G3MP2B3 calns.; B

Mass spectrum (electron ionization)

Go To: Top, Condensed phase thermochemistry data, Phase change 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: NIST Mass Spectrometry Data Center, William E. Wallace, director

Spectrum

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Mass spectrum
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Additional Data

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Owner NIST Mass Spectrometry Data Center
Collection (C) 2014 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin Japan AIST/NIMC Database- Spectrum MS-NW-1983
NIST MS number 227951

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References

Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), Notes

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

Quitzsch, Schaffernicht, et al., 1963
Quitzsch, K.; Schaffernicht, H.; Geiseler, G., Uber ein Mikro-Metallblock-Kalorimeter, Z. Phys. Chem. (Leipzig), 1963, 223, 200-206. [all data]

Kovats, Gunthard, et al., 1957
Kovats, E.; Gunthard, H.; Plattner, A., Die tabellen 4 und 5 enthalten numerische fehler und lanten richtig, Helv. Chim. Acta, 1957, 40, 000. [all data]

Kovats, Gunthard, et al., 1955
Kovats, E.; Gunthard, Hs.H.; Plattner, Pl.A., Thermische eigenschaften von azulenen, Helv. Chim. Acta, 1955, 38, 1912-1919. [all data]

Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc., Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [all data]

Turner, Meador, et al., 1957
Turner, R.B.; Meador, W.R.; Doering, W. vonE.; Knox, L.H.; Mayer, J.R.; Wiley, D.W., Heats of Hydrogenation III. Hydrogenation of Cyclooctatetraene and of Some Seven-membered Non-benzenoid Aromatic Compounds, J. Am. Chem. Soc., 1957, 79, 4127. [all data]

Birrrell, 1935
Birrrell, K.S., Studies in the Chemistry of Azulene, J. Am. Chem. Soc., 1935, 57, 893. [all data]

Chickos, Hesse, et al., 1998
Chickos, James; Hesse, Donald; Hosseini, Sarah; Nichols, Gary; Webb, Paul, Sublimation enthalpies at 298.15K using correlation gas chromatography and differential scanning calorimetry measurements, Thermochimica Acta, 1998, 313, 2, 101-110, https://doi.org/10.1016/S0040-6031(97)00432-2 . [all data]

Bauder and Gunthard, 1962
Bauder, A.; Gunthard, H.Hs., 196. Dampfdruck von azulen, Helv. Chim. Acta, 1962, 62, 1698. [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]

Meyer and Gens, 1977
Meyer, Edwin F.; Gens, Timothy H., Vapor pressure of azulene between 114 and 261.degree.C, J. Chem. Eng. Data, 1977, 22, 1, 30-31, https://doi.org/10.1021/je60072a019 . [all data]

Bauder and G«65533»nthard, 1962
Bauder, A.; G«65533»nthard, Hs.H., Dampfdruck von Azulen, Helv. Chim. Acta, 1962, 45, 5, 1698-1702, https://doi.org/10.1002/hlca.19620450536 . [all data]

Hoyer and Peperle, 1958
Hoyer, H.; Peperle, W., Z. Elektrochem., 1958, 62, 61. [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]

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]


Notes

Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), References