1,3-Cyclopentadiene, 5-(1-methylethylidene)-
- Formula: C8H10
- Molecular weight: 106.1650
- IUPAC Standard InChI: InChI=1S/C8H10/c1-7(2)8-5-3-4-6-8/h3-6H,1-2H3
- IUPAC Standard InChIKey: WXACXMWYHXOSIX-UHFFFAOYSA-N
- CAS Registry Number: 2175-91-9
- 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: 1,3-Cyclopentadiene, 5-isopropylidene-; Dimethylfulvene; Isopropylidenecyclopentadiene; 5-Isopropylidene-1,3-cyclopentadiene; 6,6-Dimethylfulvene; 5-(1-Methylethylidene)-1,3-cyclopentadiene; 5-Isopropylidenecyclopentadiene; Fulvene, 6,6-dimethyl
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Gas Chromatography, References, Notes
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°gas | 34.3 | kcal/mol | Chyd | Roth, Adamczak, et al., 1991 |
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 | -1115.5 ± 1.2 | kcal/mol | Ccb | Day and Oestreich, 1957 | Reanalyzed by Cox and Pilcher, 1970, Original value = -1114.5 kcal/mol; Corresponding ΔfHºliquid = 21.52 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
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| Tfus | 274.05 | K | N/A | Murphy and Duggan, 1949 | Uncertainty assigned by TRC = 2. K; TRC |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔvapH° | 10.56 | kcal/mol | V | Day and Oestreich, 1957 | ALS |
Reduced pressure boiling point
| Tboil (K) | Pressure (atm) | Reference | Comment |
|---|---|---|---|
| 349.7 | 0.066 | Aldrich Chemical Company Inc., 1990 | BS |
| 332. to 333. | 0.033 | Frinton Laboratories Inc., 1986 | BS |
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
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
C8H9- + =
By formula: C8H9- + H+ = C8H10
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 354.1 ± 3.2 | kcal/mol | G+TS | Brickhouse and Squires, 1988 | gas phase; Acidity between nPrSH, iPrSH; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 347.5 ± 3.0 | kcal/mol | IMRB | Brickhouse and Squires, 1988 | gas phase; Acidity between nPrSH, iPrSH; B |
3 +
=
By formula: 3H2 + C8H10 = C8H16
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -72.2 ± 0.1 | kcal/mol | Chyd | Roth, Adamczak, et al., 1991 | liquid phase; ALS |
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:
B - John E. Bartmess
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
View reactions leading to C8H10+ (ion structure unspecified)
Ionization energy determinations
| IE (eV) | Method | Reference | Comment |
|---|---|---|---|
| 8.03 | PE | Houk, George, et al., 1974 | Vertical value; LLK |
De-protonation reactions
C8H9- + =
By formula: C8H9- + H+ = C8H10
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 354.1 ± 3.2 | kcal/mol | G+TS | Brickhouse and Squires, 1988 | gas phase; Acidity between nPrSH, iPrSH; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 347.5 ± 3.0 | kcal/mol | IMRB | Brickhouse and Squires, 1988 | gas phase; Acidity between nPrSH, iPrSH; B |
Gas Chromatography
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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
Van Den Dool and Kratz RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | DB-5 | 858. | Wu, Zorn, et al., 2005 | 30. m/0.32 mm/0.25 μm, He, 40. C @ 2. min, 5. K/min, 250. C @ 5. min |
Van Den Dool and Kratz RI, polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | ZB-Wax | 1170. | Wu, Zorn, et al., 2005 | 30. m/0.32 mm/0.25 μm, He, 40. C @ 2. min, 5. K/min, 250. C @ 5. min |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Gas Chromatography, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Roth, Adamczak, et al., 1991
Roth, W.R.; Adamczak, O.; Breuckmann, R.; Lennartz, H.-W.; Boese, R.,
Die Berechnung von Resonanzenergien; das MM2ERW-Kraftfeld,
Chem. Ber., 1991, 124, 2499-2521. [all data]
Day and Oestreich, 1957
Day, J.H.; Oestreich, C.,
Fulvenes: III. Heat of combustion and resonance energy,
J. Org. Chem., 1957, 22, 214-216. [all data]
Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G.,
Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]
Murphy and Duggan, 1949
Murphy, M.T.; Duggan, A.C.,
Pyrolysis of Butadiene,
J. Am. Chem. Soc., 1949, 71, 3347. [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]
Frinton Laboratories Inc., 1986
Frinton Laboratories Inc.,
Catalog Number 11, Frinton Laboratories Inc., Vineland, NJ, 1986, 99. [all data]
Brickhouse and Squires, 1988
Brickhouse, M.D.; Squires, R.R.,
Gas Phase Bronsted vs. Lewis Acid-Base Reactions of 6,6-Dimethylfulvene. A Sensitive Probe of the Electronic Structures of Organic Anions,
J. Am. Chem. Soc., 1988, 110, 9, 2706, https://doi.org/10.1021/ja00217a002
. [all data]
Houk, George, et al., 1974
Houk, K.N.; George, J.K.; Duke, R.E., Jr.,
A frontier molecular orbital treatment of fulvene cycloadditions. Molecular orbital calculations and photoelectron spectra of substituted fulvenes,
Tetrahedron, 1974, 30, 523. [all data]
Wu, Zorn, et al., 2005
Wu, S.; Zorn, H.; Krings, U.; Berger, R.G.,
Characteristic Volatiles from Young and Aged Fruiting Bodies of Wild Polyporus sulfureus (Bull.:Fr.) Fr.,
J. Agric. Food Chem., 2005, 53, 11, 4524-4528, https://doi.org/10.1021/jf0478511
. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Gas Chromatography, References
- Symbols used in this document:
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 ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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