Dicyclopentadiene
- Formula: C10H12
- Molecular weight: 132.2023
- IUPAC Standard InChI: InChI=1S/C10H12/c1-2-9-7-4-5-8(6-7)10(9)3-1/h1-2,4-5,7-10H,3,6H2/t7?,8?,9-,10+/m1/s1
- IUPAC Standard InChIKey: HECLRDQVFMWTQS-BMNUFHGDSA-N
- CAS Registry Number: 77-73-6
- 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. - Stereoisomers:
- Other names: 4,7-Methano-1H-indene, 3a,4,7,7a-tetrahydro-; 4,7-Methanoindene, 3a,4,7,7a-tetrahydro-; Bicyclopentadiene; Bis[cyclopentadiene]; Cyclopentadiene dimer; 3a,4,7,7a-Tetrahydro-4,7-methanoindene; 3a,4,7,7a-Tetrahydro-4,7-methano-1H-indene; Tricyclo[5.2.1.02,6]deca-3,8-diene; 1,3-Cyclopentadiene, dimer; Dicyklopentadien; Dimer cyklopentadienu; UN 2048; NSC 7352; Tricyclo[5.2.1.0<2,6>]deca-3,8-diene
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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
AC - William E. Acree, Jr., James S. Chickos
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| Tboil | 443.2 | K | N/A | Aldrich Chemical Company Inc., 1990 | BS |
| Tboil | 359.2 | K | N/A | Kistiakowsky, Ruhoff, et al., 1936 | Uncertainty assigned by TRC = 50. K; this value inconsistent with other reported values; TRC |
| Quantity | Value | Units | Method | Reference | Comment |
| Tfus | 306.8 | K | N/A | Kistiakowsky, Ruhoff, et al., 1936 | Uncertainty assigned by TRC = 0.5 K; Note: the boiling point reported for this compound was incorrect; TRC |
| Tfus | 305. | K | N/A | Stobbe and Reuss, 1912 | Uncertainty assigned by TRC = 4. K; TRC |
| Quantity | Value | Units | Method | Reference | Comment |
| Ttriple | 304.8 | K | N/A | Lebedev and Lityagov, 1977 | Crystal phase 1 phase; Uncertainty assigned by TRC = 0.2 K; TRC |
Enthalpy of vaporization
| ΔvapH (kcal/mol) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 10.1 | 322. | Stull, 1947 | Based on data from 307. to 440. K.; AC |
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 by: 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
= 2
By formula: C10H12 = 2C5H6
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 17.300 | kcal/mol | Cm | Baur and Frater, 1941 | gas phase; Heat of dissociation |
References
Go To: Top, Phase change data, Reaction thermochemistry data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc.,
Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [all data]
Kistiakowsky, Ruhoff, et al., 1936
Kistiakowsky, G.B.; Ruhoff, J.R.; Smith, H.A.; Vaughan, W.E.,
Heats of Organic Reactions IV. Hydrogenation of Some Dienes and of Benzene,
J. Am. Chem. Soc., 1936, 58, 146-53. [all data]
Stobbe and Reuss, 1912
Stobbe, H.; Reuss, F.,
Polymerization of Cyclopentadienes,
Justus Liebigs Ann. Chem., 1912, 391, 151. [all data]
Lebedev and Lityagov, 1977
Lebedev, B.V.; Lityagov, V.Ya.,
Thermodynamics of polypentenamer synthesis reactions crystalline polytetrahydrofuran at 0 K,
Vysokomol. Soedin., Ser. B, 1977, 19, 558. [all data]
Stull, 1947
Stull, Daniel R.,
Vapor Pressure of Pure Substances. Organic and Inorganic Compounds,
Ind. Eng. Chem., 1947, 39, 4, 517-540, https://doi.org/10.1021/ie50448a022
. [all data]
Baur and Frater, 1941
Baur, E.; Frater, S.,
Kinetik der bildung und des zerfalls von dicyclopentadien,
Helv. Chim. Acta, 1941, 24, 768-783. [all data]
Notes
Go To: Top, Phase change data, Reaction thermochemistry data, References
- Symbols used in this document:
Tboil Boiling point Tfus Fusion (melting) point Ttriple Triple point temperature ΔrH° Enthalpy of reaction at standard conditions ΔvapH Enthalpy of vaporization - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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