1,3-Cyclopentadiene, 1,2,3,4,5-pentamethyl-
- Formula: C10H16
- Molecular weight: 136.2340
- IUPAC Standard InChI: InChI=1S/C10H16/c1-6-7(2)9(4)10(5)8(6)3/h6H,1-5H3
- IUPAC Standard InChIKey: WQIQNKQYEUMPBM-UHFFFAOYSA-N
- CAS Registry Number: 4045-44-7
- 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: Cyclopentadiene, 1,2,3,4,5-pentamethyl-; 1,2,3,4,5-Pentamethylcyclopentadiene; 1,2,3,4,5-Pentamethyl-1,3-cyclopentadiene; Pentamethylcyclopentadiene
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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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°gas | -5.9 | kcal/mol | Chyd | Roth, Adamczak, et al., 1991 |
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 by: Robert L. Brown and Stephen E. Stein
Reduced pressure boiling point
| Tboil (K) | Pressure (atm) | Reference |
|---|---|---|
| 331.2 | 0.017 | Aldrich Chemical Company Inc., 1990 |
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
C10H15- + =
By formula: C10H15- + H+ = C10H16
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 360.8 ± 2.2 | kcal/mol | G+TS | Taft, 1987 | gas phase; value altered from reference due to change in acidity scale; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 355.0 ± 2.0 | kcal/mol | IMRE | Taft, 1987 | gas phase; value altered from reference due to change in acidity scale; B |
2 +
=
By formula: 2H2 + C10H16 = C10H20
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -45.0 ± 0.2 | 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
LL - Sharon G. Lias and Joel F. Liebman
Ionization energy determinations
| IE (eV) | Method | Reference | Comment |
|---|---|---|---|
| 7.17 | PE | Kiselev, Sakhabutdinov, et al., 1992 | LL |
| 7.35 | PE | Kiselev, Sakhabutdinov, et al., 1992 | Vertical value; LL |
De-protonation reactions
C10H15- + =
By formula: C10H15- + H+ = C10H16
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 360.8 ± 2.2 | kcal/mol | G+TS | Taft, 1987 | gas phase; value altered from reference due to change in acidity scale; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 355.0 ± 2.0 | kcal/mol | IMRE | Taft, 1987 | gas phase; value altered from reference due to change in acidity scale; B |
References
Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, 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]
Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc.,
Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [all data]
Taft, 1987
Taft, R.W.,
The Nature and Analysis of Substitutent Electronic Effects,
Personal communication. See also Prog. Phys. Org. Chem., 1987, 16, 1. [all data]
Kiselev, Sakhabutdinov, et al., 1992
Kiselev, V.D.; Sakhabutdinov, A.G.; Shakirov, I.M.; Zverev, V.V.; Konovalov, A.I.,
Bis reactants in Diels-Alder reactions. VII. Preparation and properties of polyadducts of reactions of bis(polymethylcyclopentadienes) and bis(maleimides),
Zh. Org. Khim., 1992, 28, 2244. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, References
- Symbols used in this document:
Tboil Boiling point 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 - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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