Bicyclo[4.4.1]undeca-1,3,5,7,9-pentaene

• Formula: C₁₁H₁₀
• Molecular weight: 142.1971
• IUPAC Standard InChI: InChI=1S/C11H10/c1-2-6-11-8-4-3-7-10(5-1)9-11/h1-8H,9H2 Copy

  
• IUPAC Standard InChIKey: OORRQYZWSVJKSO-UHFFFAOYSA-N Copy
• CAS Registry Number: 2443-46-1
• Chemical structure:
  This structure is also available as a 2d Mol file or as a computed 3d SD file
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• Other names: 1,6-Methano[10]annulene
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• Information on this page:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • Gas phase ion energetics data
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
  • References
  • Notes
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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

Constant pressure heat capacity of gas

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

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
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.

Reduced pressure boiling point

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 compiled as indicated in comments:
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

View reactions leading to C₁₁H₁₀⁺ (ion structure unspecified)

Ionization energy determinations

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

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, Alexander N. Yermakov, Alexy A. Usov, Antonina A. Goncharova, Axlexander N. Leskin, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina

Spectrum

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Additional Data

References

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

Roth, Klarner, et al., 1992
Roth, W.R.; Klarner, F.-G.; Siepert, G.; Lennartz, H.-W., Zur Frage der Homoaromatizitat von Norcaradien und Cycloheptatrien, Chem. Ber., 1992, 125, 217-224. [all data]

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]

Bremser, Hagen, et al., 1969
Bremser, W.; Hagen, R.; Heilbronner, E.; Vogel, E., 48. Die Bildungsenthalpie 1,6-uberbruckter [10]Annulene, Helv. Chim. Acta, 1969, 52, 418-431. [all data]

Espinosa-Muller A., 1978
Espinosa-Muller A., Conformational and thermodynamical prediction of the 1,5-methano(10)-annulene, 1,6-methano(10)-annulene, and some benzo derivatives, J. Chem. Phys., 1978, 69, 367-372. [all data]

Buckingham and Donaghy, 1982
Buckingham, J.; Donaghy, S.M., Dictionary of Organic Compounds: Fifth Edition, Chapman and Hall, New York, 1982, 1. [all data]

Andrea, Cerfontain, et al., 1984
Andrea, R.R.; Cerfontain, H.; Lamberchts, H.J.A.; Louwen, J.N.; Oskam, A., He I and He II photoelectron spectra and CNDO/S and MNDO MO calculations of some bridged [10] annulenes, J. Am. Chem. Soc., 1984, 106, 2531. [all data]

Boschi, Schmidt, et al., 1972
Boschi, R.; Schmidt, W.; Gfeller, J.-C., The electronic structure of 1,6-methano-cyclodecapentaene, Tetrahedron Lett., 1972, 40, 4107. [all data]

Vogel and Roth, 1966
Vogel, E.; Roth, H.D., UV atlas of organic compounds, 1966, 1, A15/5. [all data]

Notes

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• Symbols used in this document:
  

  Cp,gas	Constant pressure heat capacity of gas
  Tboil	Boiling point
  Tfus	Fusion (melting) point
  ΔcH°liquid	Enthalpy of combustion of liquid at standard conditions
  ΔfH°gas	Enthalpy of formation of gas at standard conditions
  ΔfH°liquid	Enthalpy of formation of liquid at standard conditions
  ΔvapH°	Enthalpy of vaporization at standard conditions

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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