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Azulene

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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
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow

Quantity Value Units Method Reference Comment
Deltafgas73.5kcal/molChydRoth, Bohm, et al., 1983ALS
Deltafgas66.9kcal/molCcbKovats, Gunthard, et al., 1957Correction to Kovats, Gunthard, et al., 1955; ALS

Constant pressure heat capacity of gas

Cp,gas (cal/mol*K) Temperature (K) Reference Comment
19.59200.Kovats E., 1955GT
30.691298.15
30.930300.
42.151400.
51.690500.
59.319600.
65.559700.
70.590800.
74.749900.
78.2411000.

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
Deltacliquid-1265.1 ± 0.6kcal/molCcbQuitzsch, Schaffernicht, et al., 1963Corresponding «DELTA»fliquid = 51.3 kcal/mol (simple calculation by NIST; no Washburn corrections)
Quantity Value Units Method Reference Comment
Deltafsolid50.7kcal/molCcbKovats, Gunthard, et al., 1957Correction to Kovats, Gunthard, et al., 1955
Quantity Value Units Method Reference Comment
Deltacsolid-1264.5kcal/molCcbKovats, Gunthard, et al., 1957Correction to Kovats, Gunthard, et al., 1955; Corresponding «DELTA»fsolid = 50.7 kcal/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
Deltavap12.6kcal/molCGCChickos, Hesse, et al., 1998AC
Deltavap15.24 ± 0.05kcal/molVBauder and Gunthard, 1962ALS
Quantity Value Units Method Reference Comment
Deltasub19. ± 5.kcal/molAVGN/AAverage of 7 values; Individual data points

Enthalpy of vaporization

DeltavapH (kcal/mol) Temperature (K) Method Reference Comment
12.7384.AStephenson and Malanowski, 1987Based on data from 369. - 515. K.; AC
12.2457.EBMeyer and Gens, 1977Based on data from 442. - 534. K.; AC
13.3373.N/ABauder and G«65533»nthard, 1962Based on data from 373. - 423. K.; AC

Enthalpy of sublimation

DeltasubH (kcal/mol) Temperature (K) Method Reference Comment
18.7 ± 0.31303.HSAChickos, Hesse, et al., 1998Based on data from 283. - 326. K.; AC
19.8305.SStephenson and Malanowski, 1987Based on data from 290. - 372. K.; AC
18.1273.N/AHoyer and Peperle, 1958Based on data from 253. - 293. K.; AC

Enthalpy of fusion

DeltafusH (kcal/mol) Temperature (K) Method Reference Comment
4.190373.5DSCChickos, 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:


Reaction 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:
B - John E. Bartmess
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. A general reaction search form is also available. Future versions of this site may rely on reaction search pages in place of the enumerated reaction displays seen below.

Individual Reactions

C10H7- + Hydrogen cation = Azulene

By formula: C10H7- + H+ = C10H8

Quantity Value Units Method Reference Comment
Deltar367.7 ± 2.5kcal/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
Deltar360.2 ± 2.0kcal/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

C6H7N+ + Azulene = (C6H7N+ bullet Azulene)

By formula: C6H7N+ + C10H8 = (C6H7N+ bullet C10H8)

Bond type: Charge transfer bond (positive ion)

Quantity Value Units Method Reference Comment
Deltar14.0kcal/molPHPMSMeot-Ner (Mautner) and El-Shall, 1986gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Deltar26.cal/mol*KN/AMeot-Ner (Mautner) and El-Shall, 1986gas phase; Entropy change calculated or estimated; M

Free energy of reaction

DeltarG° (kcal/mol) T (K) Method Reference Comment
5.8315.PHPMSMeot-Ner (Mautner) and El-Shall, 1986gas phase; Entropy change calculated or estimated; M

5Hydrogen + Azulene = Bicyclo[5.3.0]decane

By formula: 5H2 + C10H8 = C10H18

Quantity Value Units Method Reference Comment
Deltar-98.98 ± 0.13kcal/molChydTurner, Meador, et al., 1957, 2liquid phase; solvent: Acetic acid; ALS

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)221.1kcal/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity214.kcal/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., 1986«DELTA»Gea(423 K) = -18.0 kcal/mol; «DELTA»Sea = +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 (kcal/mol) Reference Comment
221.7Aue, Guidoni, et al., 2000Experimental literature data re-evaluated by the authors using ab initio protonation entropies; MM

Gas basicity at 298K

Gas basicity (review) (kcal/mol) Reference Comment
214.3Aue, 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
Deltar367.7 ± 2.5kcal/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
Deltar360.2 ± 2.0kcal/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

Ion clustering data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, NIST Free Links, 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: Michael M. Meot-Ner (Mautner) and Sharon G. Lias

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. Searches may be limited to ion clustering reactions. A general reaction search form is also available.

Clustering reactions

C6H7N+ + Azulene = (C6H7N+ bullet Azulene)

By formula: C6H7N+ + C10H8 = (C6H7N+ bullet C10H8)

Bond type: Charge transfer bond (positive ion)

Quantity Value Units Method Reference Comment
Deltar14.0kcal/molPHPMSMeot-Ner (Mautner) and El-Shall, 1986gas phase; Entropy change calculated or estimated
Quantity Value Units Method Reference Comment
Deltar26.cal/mol*KN/AMeot-Ner (Mautner) and El-Shall, 1986gas phase; Entropy change calculated or estimated

Free energy of reaction

DeltarG° (kcal/mol) T (K) Method Reference Comment
5.8315.PHPMSMeot-Ner (Mautner) and El-Shall, 1986gas phase; Entropy change calculated or estimated

IR Spectrum

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

Gas Phase Spectrum

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IR spectrum
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Additional Data

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Owner NIST Standard Reference Data Program
Collection (C) 2018 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin Sadtler Research Labs Under US-EPA Contract
State gas

This IR spectrum is from the NIST/EPA Gas-Phase Infrared Database .


Mass spectrum (electron ionization)

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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: 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

All mass spectra in this site (plus many more) are available from the NIST/EPA/NIH Mass Spectral Library. Please see the following for information about the library and its accompanying search program.


UV/Visible spectrum

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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: Victor Talrose, Eugeny B. Stern, Antonina A. Goncharova, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina

Spectrum

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UVVis spectrum
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Additional Data

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Source Nozoe, Seto, et al., 1962
Owner INEP CP RAS, NIST OSRD
Collection (C) 2007 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin INSTITUTE OF ENERGY PROBLEMS OF CHEMICAL PHYSICS, RAS
Source reference RAS UV No. 3172
Instrument n.i.g.
Melting point 99
Boiling point 270; 125(10)

Gas Chromatography

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, NIST Free Links, 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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Column type Active phase Temperature (C) I Reference Comment
PackedC78, Branched paraffin130.1326.0Dallos, Sisak, et al., 2000He; Column length: 3.3 m
PackedC78, Branched paraffin130.1329.7Reddy, Dutoit, et al., 1992Chromosorb G HP; Column length: 3.3 m
CapillaryOV-1130.1296.Engewald, Wennrich, et al., 1979Column length: 50. m; Column diameter: 0.23 mm

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

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Column type Active phase I Reference Comment
CapillaryDB-51311.Rostad and Pereira, 198630. m/0.26 mm/0.25 «mu»m, He, 50. C @ 4. min, 6. K/min, 300. C @ 20. min
CapillarySE-521292.Carugno and Rossi, 1967N2, 1.8 K/min; Column length: 65. m; Column diameter: 0.3 mm; Tstart: 100. C; Tend: 300. C

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

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Column type Active phase I Reference Comment
CapillaryDB-Wax1706.Shimoda, Wu, et al., 199660. m/0.25 mm/0.25 «mu»m, He, 3. K/min; Tstart: 50. C; Tend: 230. C

Normal alkane RI, non-polar column, temperature ramp

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Column type Active phase I Reference Comment
CapillaryMethylsiloxane + 5 % Ph-groups1299.Nadim, Malik, et al., 201130. m/0.25 mm/0.25 «mu»m, Helium, 60. C @ 2. min, 7. K/min, 230. C @ 20. min

Normal alkane RI, polar column, temperature ramp

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Column type Active phase I Reference Comment
CapillaryFFAP1729.Piyachaiseth, Jirapakkul, et al., 201160. m/0.25 mm/0.25 «mu»m, Helium, 45. C @ 1. min, 5. K/min, 220. C @ 5. min
CapillaryInnowax1746.Kaypak and Avsar, 200830. m/0.25 mm/0.25 «mu»m, 40. C @ 5. min, 10. K/min, 200. C @ 15. min

Normal alkane RI, polar column, custom temperature program

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Column type Active phase I Reference Comment
CapillarySupelcowax-101736.Lee and Kim, 200230. m/0.32 mm/0.25 «mu»m, Helium; Program: 40 0C (5 min) 4 0C/min -> 150 0C 8 0C/min -> 240 0C
CapillaryCP-Wax 52CB1710.Vernin, 1991Column length: 50. m; Column diameter: 0.32 mm; Program: not specified

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

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Column type Active phase I Reference Comment
CapillaryDB-5223.74Rostad and Pereira, 198630. m/0.26 mm/0.25 «mu»m, He, 50. C @ 4. min, 6. K/min, 300. C @ 20. min
CapillarySE-52219.95Lee, Vassilaros, et al., 197912. m/0.3 mm/0.34 «mu»m, He, 2. K/min; Tstart: 50. C; Tend: 250. C

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, NIST Free Links, Notes

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

Roth, Bohm, et al., 1983
Roth, W.R.; Bohm, M.; Lenhartz, H-W.; Vogel, E., Heats of hydrogenation. Part 5. Resonance energy of bridged [10]annulenes, Angew. Chem., 1983, 95, 1011-1012. [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]

Kovats E., 1955
Kovats E., Thermochemical properties of azulene, Helv. Chim. Acta, 1955, 38, 1912-1919. [all data]

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]

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]

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]

Meot-Ner (Mautner) and El-Shall, 1986
Meot-Ner (Mautner), M.; El-Shall, M.S., Ionic Charge Transfer Complexes. 1. Cationic Complexes with Delocalized and Partially Localized pi Systems, J. Am. Chem. Soc., 1986, 108, 15, 4386, https://doi.org/10.1021/ja00275a026 . [all data]

Turner, Meador, et al., 1957, 2
Turner, R.B.; Meador, W.R.; Doering, W.E.; Knox, L.H.; Mayer, J.R.; Wiley, D.W., Heats of hydrogenation. III. Hydrogenation of cycllooctatetraene and of some seven-membered non-benzenoid aromatic compounds, J. Am. Chem. Soc., 1957, 79, 4127-4133. [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]

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Notes

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