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
- IUPAC Standard InChIKey: OORRQYZWSVJKSO-UHFFFAOYSA-N
- 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
The 3d structure may be viewed using Java or Javascript. - Other names: 1,6-Methano[10]annulene
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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 |
|---|---|---|---|---|---|
| ΔfH°gas | 77.1 | kcal/mol | Chyd | Roth, Klarner, et al., 1992 | see Roth, Bohm, et al., 1983; ALS |
| ΔfH°gas | 75.2 ± 0.6 | kcal/mol | Ccb | Bremser, Hagen, et al., 1969 | ALS |
Constant pressure heat capacity of gas
| Cp,gas (cal/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 11.33 | 100. | Espinosa-Muller A., 1978 | These values were calculated by a method of force field; their uncertainties may exceed 5-10 J/mol*K.; GT |
| 22.18 | 200. | ||
| 34.651 | 298.15 | ||
| 34.880 | 300. | ||
| 47.070 | 400. | ||
| 57.720 | 500. | ||
| 66.561 | 600. | ||
| 73.891 | 700. | ||
| 80.010 | 800. | ||
| 85.151 | 900. | ||
| 89.491 | 1000. |
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.
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| Tfus | 301. to 302. | K | N/A | Buckingham and Donaghy, 1982 | BS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔvapH° | 14.52 | kcal/mol | V | Bremser, Hagen, et al., 1969 | ALS |
| ΔvapH° | 14.6 | kcal/mol | N/A | Bremser, Hagen, et al., 1969 | DRB |
Reduced pressure boiling point
| Tboil (K) | Pressure (atm) | Reference | Comment |
|---|---|---|---|
| 341. to 345. | 0.001 | Buckingham and Donaghy, 1982 | BS |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry data, Phase change 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 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
| IE (eV) | Method | Reference | Comment |
|---|---|---|---|
| 7.7 | PE | Andrea, Cerfontain, et al., 1984 | LBLHLM |
| 7.92 | PE | Andrea, Cerfontain, et al., 1984 | Vertical value; LBLHLM |
| 7.90 | PE | Boschi, Schmidt, et al., 1972 | Vertical value; LLK |
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]
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 ΔfH°gas Enthalpy of formation of gas at standard conditions ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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