Azulene
- Formula: C10H8
- Molecular weight: 128.1705
- IUPAC Standard InChIKey: CUFNKYGDVFVPHO-UHFFFAOYSA-N
- 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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Condensed phase thermochemistry data
Go To: Top, Phase change data, 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: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔcH°liquid | -5293. ± 3. | kJ/mol | Ccb | Quitzsch, Schaffernicht, et al., 1963 | Corresponding ΔfHºliquid = 215. kJ/mol (simple calculation by NIST; no Washburn corrections) |
Quantity | Value | Units | Method | Reference | Comment |
ΔfH°solid | 212. | kJ/mol | Ccb | Kovats, Gunthard, et al., 1957 | Correction to Kovats, Gunthard, et al., 1955 |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°solid | -5290.7 | kJ/mol | Ccb | Kovats, Gunthard, et al., 1957 | Correction to Kovats, Gunthard, et al., 1955; Corresponding ΔfHºsolid = 212. kJ/mol (simple calculation by NIST; no Washburn corrections) |
Phase change data
Go To: Top, Condensed phase thermochemistry data, 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 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 |
---|---|---|---|---|---|
Tboil | 515.2 | K | N/A | Aldrich Chemical Company Inc., 1990 | BS |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 373. | K | N/A | Turner, Meador, et al., 1957 | Uncertainty assigned by TRC = 2. K; TRC |
Tfus | 303.65 | K | N/A | Birrrell, 1935 | Uncertainty assigned by TRC = 1. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 52.8 | kJ/mol | CGC | Chickos, Hesse, et al., 1998 | AC |
ΔvapH° | 63.8 ± 0.2 | kJ/mol | V | Bauder and Gunthard, 1962 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 80. ± 20. | kJ/mol | AVG | N/A | Average of 7 values; Individual data points |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
53.0 | 384. | A | Stephenson and Malanowski, 1987 | Based on data from 369. to 515. K.; AC |
51.2 | 457. | EB | Meyer and Gens, 1977 | Based on data from 442. to 534. K.; AC |
55.5 | 373. | N/A | Bauder and G«65533»nthard, 1962 | Based on data from 373. to 423. K.; AC |
Enthalpy of sublimation
ΔsubH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
78.4 ± 1.3 | 303. | HSA | Chickos, Hesse, et al., 1998 | Based on data from 283. to 326. K.; AC |
82.8 | 305. | S | Stephenson and Malanowski, 1987 | Based on data from 290. to 372. K.; AC |
75.8 | 273. | N/A | Hoyer and Peperle, 1958 | Based on data from 253. to 293. K.; AC |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
17.53 | 373.5 | DSC | Chickos, Hesse, et al., 1998 | AC |
Gas phase ion energetics data
Go To: Top, Condensed phase thermochemistry data, Phase change 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 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 ± 0.02 | eV | N/A | N/A | L |
Quantity | Value | Units | Method | Reference | Comment |
Proton affinity (review) | 925.2 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 896. | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Electron affinity determinations
EA (eV) | Method | Reference | Comment |
---|---|---|---|
0.7900 ± 0.0080 | LPES | Schiedt, Knott, et al., 2000 | B |
0.69 ± 0.10 | TDEq | Chowdhury, Heinis, et al., 1986 | ΔGea(423 K) = -18.0 kcal/mol; ΔSea = +4.5 eu.; B |
0.80 ± 0.10 | LPES | Ando, Mitsui, et al., 2008 | Stated electron affinity is the Vertical Detachment Energy; B |
0.690 ± 0.040 | ECD | Chen, Chen, et al., 1992 | B |
0.681 ± 0.043 | Kine | Grimsrud, Chowdhury, et al., 1985 | B |
0.6560 ± 0.0080 | ECD | Becker and Chen, 1966 | B |
<0.520 ± 0.013 | ECD | Wojnarovits and Foldiak, 1981 | EA is an upper limit: Chen and Wentworth, 1989. G3MP2B3 calculations indicate an EA of ca. 0.6 eV.; B |
>0.460008 | ES | Chaney, Christophorou, et al., 1970 | Lifetime: Compton and Huebner, 1969; B |
Proton affinity at 298K
Proton affinity (kJ/mol) | Reference | Comment |
---|---|---|
927.6 | Aue, Guidoni, et al., 2000 | Experimental literature data re-evaluated by the authors using ab initio protonation entropies; MM |
Gas basicity at 298K
Gas basicity (review) (kJ/mol) | Reference | Comment |
---|---|---|
896.6 | Aue, Guidoni, et al., 2000 | Experimental literature data re-evaluated by the authors using ab initio protonation entropies; MM |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
7.38 ± 0.03 | PI | Jochims, Rasekh, et al., 1992 | LL |
7.32 ± 0.05 | EQ | Mautner(Meot-Ner), Nelsen, et al., 1984 | LBLHLM |
7.41 ± 0.05 | EQ | Mautner(Meot-Ner), 1980 | LLK |
7.43 ± 0.04 | PE | Boschi, Clar, et al., 1974 | LLK |
7.43 ± 0.01 | PE | Dewar and Worley, 1969 | RDSH |
7.42 ± 0.05 | PE | Eland and Danby, 1968 | RDSH |
7.41 | PI | Kitagawa, Inokuchi, et al., 1966 | RDSH |
7.408 | S | Kitagawa, Harada, et al., 1966 | RDSH |
7.431 ± 0.006 | S | Clark, 1965 | RDSH |
7.4 | CTS | Finch, 1964 | RDSH |
7.42 | PE | Dougherty, Lewis, et al., 1980 | Vertical value; LLK |
7.44 ± 0.03 | PE | Heilbronner, Hoshi, et al., 1976 | Vertical value; LLK |
Appearance energy determinations
De-protonation reactions
C10H7- + =
By formula: C10H7- + H+ = C10H8
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1538. ± 10. | kJ/mol | TDEq | Meot-ner, Liebman, et al., 1988 | gas 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 |
ΔrG° | 1507. ± 8.4 | kJ/mol | TDEq | Meot-ner, Liebman, et al., 1988 | gas 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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Additional Data
View image of digitized spectrum (can be printed in landscape orientation).
Due to licensing restrictions, this spectrum cannot be downloaded.
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 |
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,
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Birrrell, 1935
Birrrell, K.S.,
Studies in the Chemistry of Azulene,
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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,
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. [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,
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. [all data]
Meyer and Gens, 1977
Meyer, Edwin F.; Gens, Timothy H.,
Vapor pressure of azulene between 114 and 261.degree.C,
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. [all data]
Bauder and G«65533»nthard, 1962
Bauder, A.; G«65533»nthard, Hs.H.,
Dampfdruck von Azulen,
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. [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,
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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,
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. [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,
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. [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,
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Becker and Chen, 1966
Becker, R.S.; Chen, E.,
Extension of Electron Affinities and Ionization Potentials of Aromatic Hydrocarbons,
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Wojnarovits and Foldiak, 1981
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Electron capture detection of aromatic hydrocarbons,
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Chen and Wentworth, 1989
Chen, E.C.M.; Wentworth, W.E.,
Experimental Determination of Electron Affinities of Organic Molecules,
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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,
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. [all data]
Compton and Huebner, 1969
Compton, R.N.; Huebner, R.H.,
Temporary Attachment of Electrons to Azulene-h8 and Azulene-d8,
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. [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,
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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,
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Special effects of an unusually large neutral to radical cation geometry change. Adiabatic ionization energies and proton affinities of alkylhydrazines,
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Ion thermochemistry of low volatility compounds in the gas phase. 3. Polycyclic aromatics: Ionization energies, proton, and hydrogen affinities. Extrapolations to graphite,
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Inner ionization potentials of aromatic compounds,
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Photoionization of polycyclic aromatic compounds in vacuum ultraviolet region. Azulene,
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Kitagawa, Harada, et al., 1966
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Absorption spectrum of vapor phase azulene in vacuum ultraviolet region,
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Clark, 1965
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Ionization potential of azulene,
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Finch, 1964
Finch, A.C.M.,
Charge-transfer spectra and the ionization energy of azulene,
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Dougherty, Lewis, et al., 1980
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Photoelectron spectroscopy of azulenes,
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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,
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A mass spectrometric investigation of nickel tetracarbonyl and iron pentacarbonyl,
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. [all data]
Notes
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), References
- Symbols used in this document:
AE Appearance energy EA Electron affinity IE (evaluated) Recommended ionization energy Tboil Boiling point Tfus Fusion (melting) point ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔfH°solid Enthalpy of formation of solid at standard conditions ΔfusH Enthalpy of fusion ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔsubH Enthalpy of sublimation ΔsubH° Enthalpy of sublimation at standard conditions 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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