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
Δfgas308.kJ/molChydRoth, Bohm, et al., 1983ALS
Δfgas280.kJ/molCcbKovats, Gunthard, et al., 1957Correction to Kovats, Gunthard, et al., 1955; ALS

Constant pressure heat capacity of gas

Cp,gas (J/mol*K) Temperature (K) Reference Comment
81.96200.Kovats E., 1955GT
128.41298.15
129.41300.
176.36400.
216.27500.
248.19600.
274.30700.
295.35800.
312.75900.
327.361000.

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:


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
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

C6H7N+ + Azulene = (C6H7N+ • Azulene)

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

Bond type: Charge transfer bond (positive ion)

Quantity Value Units Method Reference Comment
Δr58.6kJ/molPHPMSMeot-Ner (Mautner) and El-Shall, 1986gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Δr110.J/mol*KN/AMeot-Ner (Mautner) and El-Shall, 1986gas phase; Entropy change calculated or estimated; M

Free energy of reaction

ΔrG° (kJ/mol) T (K) Method Reference Comment
24.315.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
Δr-414.1 ± 0.54kJ/molChydTurner, Meador, et al., 1957, 2liquid phase; solvent: Acetic acid; ALS

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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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

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)

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, 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]

Nozoe, Seto, et al., 1962
Nozoe, T.; Seto, S.; Matsumura, S.; Murase, Y., The synthesis of azulene derivatives from troponoids, Bull. Chem. Soc. Jpn., 1962, 35, 7, 1179-1188. [all data]


Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, References