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. |
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 |
|---|---|---|---|---|---|
| ΔfH°liquid | 60.7 ± 0.5 | kcal/mol | Ccb | Bremser, Hagen, et al., 1969 | |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°liquid | -1436.90 | kcal/mol | Ccb | Bremser, Hagen, et al., 1969 | Corresponding ΔfHºliquid = 60.76 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
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
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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
| 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 |
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.
Spectrum
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Additional Data
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| Source | Vogel and Roth, 1966 |
|---|---|
| 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. 19934 |
| Instrument | Cary 14 |
| Melting point | 28-29 |
| Boiling point | 76-78 |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, 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, 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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