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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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, 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:
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 |
---|---|---|---|---|---|
ΔfH°gas | 73.5 | kcal/mol | Chyd | Roth, Bohm, et al., 1983 | ALS |
ΔfH°gas | 66.9 | kcal/mol | Ccb | Kovats, Gunthard, et al., 1957 | Correction to Kovats, Gunthard, et al., 1955; ALS |
Constant pressure heat capacity of gas
Cp,gas (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
19.59 | 200. | Kovats E., 1955 | GT |
30.691 | 298.15 | ||
30.930 | 300. | ||
42.151 | 400. | ||
51.690 | 500. | ||
59.319 | 600. | ||
65.559 | 700. | ||
70.590 | 800. | ||
74.749 | 900. | ||
78.241 | 1000. |
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 |
---|---|---|---|---|---|
ΔcH°liquid | -1265.1 ± 0.6 | kcal/mol | Ccb | Quitzsch, Schaffernicht, et al., 1963 | Corresponding ΔfHºliquid = 51.3 kcal/mol (simple calculation by NIST; no Washburn corrections) |
Quantity | Value | Units | Method | Reference | Comment |
ΔfH°solid | 50.7 | kcal/mol | Ccb | Kovats, Gunthard, et al., 1957 | Correction to Kovats, Gunthard, et al., 1955 |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°solid | -1264.5 | kcal/mol | Ccb | Kovats, Gunthard, et al., 1957 | Correction to Kovats, Gunthard, et al., 1955; Corresponding ΔfHºsolid = 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 |
---|---|---|---|---|---|
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° | 12.6 | kcal/mol | CGC | Chickos, Hesse, et al., 1998 | AC |
ΔvapH° | 15.24 ± 0.05 | kcal/mol | V | Bauder and Gunthard, 1962 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 19. ± 5. | kcal/mol | AVG | N/A | Average of 7 values; Individual data points |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
12.7 | 384. | A | Stephenson and Malanowski, 1987 | Based on data from 369. to 515. K.; AC |
12.2 | 457. | EB | Meyer and Gens, 1977 | Based on data from 442. to 534. K.; AC |
13.3 | 373. | N/A | Bauder and G«65533»nthard, 1962 | Based on data from 373. to 423. K.; AC |
Enthalpy of sublimation
ΔsubH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
18.7 ± 0.31 | 303. | HSA | Chickos, Hesse, et al., 1998 | Based on data from 283. to 326. K.; AC |
19.8 | 305. | S | Stephenson and Malanowski, 1987 | Based on data from 290. to 372. K.; AC |
18.1 | 273. | N/A | Hoyer and Peperle, 1958 | Based on data from 253. to 293. K.; AC |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
4.190 | 373.5 | DSC | Chickos, Hesse, et al., 1998 | AC |
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- + =
By formula: C10H7- + H+ = C10H8
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 367.7 ± 2.5 | kcal/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° | 360.2 ± 2.0 | kcal/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 |
By formula: C6H7N+ + C10H8 = (C6H7N+ • C10H8)
Bond type: Charge transfer bond (positive ion)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 14.0 | kcal/mol | PHPMS | Meot-Ner (Mautner) and El-Shall, 1986 | gas phase; Entropy change calculated or estimated; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 26. | cal/mol*K | N/A | Meot-Ner (Mautner) and El-Shall, 1986 | gas phase; Entropy change calculated or estimated; M |
Free energy of reaction
ΔrG° (kcal/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
5.8 | 315. | PHPMS | Meot-Ner (Mautner) and El-Shall, 1986 | gas phase; Entropy change calculated or estimated; M |
By formula: 5H2 + C10H8 = C10H18
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -98.98 ± 0.13 | kcal/mol | Chyd | Turner, Meador, et al., 1957, 2 | liquid 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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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 |
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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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 |
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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Additional Data
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Download spectrum in JCAMP-DX format.
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
- Symbols used in this document:
Cp,gas Constant pressure heat capacity of gas T Temperature 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°gas Enthalpy of formation of gas 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 ΔrS° Entropy 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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