endo-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-KYXWUPHJSA-N
- CAS Registry Number: 1755-01-7
- 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. - Stereoisomers:
- Other names: (3aα,4α,7α,7aα)-3a,4,7,7a-Tetrahydro-4,7-methano-1H-indene; 4,7-Methano-1H-indene, 3a,4,7,7a-tetrahydro-, (3aα,4α,7α,7aα)-
- Permanent link for this species. Use this link for bookmarking this species for future reference.
- Information on this page:
- Data at other public NIST sites:
- Options:
Data at NIST subscription sites:
NIST subscription sites provide data under the NIST Standard Reference Data Program, but require an annual fee to access. The purpose of the fee is to recover costs associated with the development of data collections included in such sites. Your institution may already be a subscriber. Follow the links above to find out more about the data in these sites and their terms of usage.
Condensed phase thermochemistry data
Go To: Top, Phase change data, Reaction thermochemistry 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:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔcH°solid | -5766.8 ± 5.9 | kJ/mol | Ccb | Becker and Roth, 1934 | Reanalyzed by Cox and Pilcher, 1970, Original value = -5767.2 kJ/mol; Corresponding ΔfHºsolid = 116.7 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| S°solid,1 bar | 230.0 | J/mol*K | N/A | Lebedev and Lityagov, 1977 | DH |
Constant pressure heat capacity of solid
| Cp,solid (J/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 188.7 | 298.15 | Lebedev and Lityagov, 1977 | T = 14 to 330 K.; DH |
Phase change data
Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry 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:
AC - William E. Acree, Jr., James S. Chickos
DH - Eugene S. Domalski and Elizabeth D. Hearing
Enthalpy of vaporization
| ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 43.6 | 365. | A | Stephenson and Malanowski, 1987 | Based on data from 350. to 446. K.; AC |
Enthalpy of fusion
| ΔfusH (kJ/mol) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 1.79 | 304.7 | Smirnova, Lebedev, et al., 1997 | AC |
| 2.22 | 304.8 | Domalski and Hearing, 1996 | AC |
Enthalpy of phase transition
| ΔHtrs (kJ/mol) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
|---|---|---|---|---|---|
| 9.660 | 216. | crystaline, II | crystaline, I | Lebedev and Lityagov, 1977 | DH |
| 2.220 | 304.8 | crystaline, I | liquid | Lebedev and Lityagov, 1977 | DH |
Entropy of phase transition
| ΔStrs (J/mol*K) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
|---|---|---|---|---|---|
| 40.0 | 216. | crystaline, II | crystaline, I | Lebedev and Lityagov, 1977 | DH |
| 6.1 | 304.8 | crystaline, I | liquid | Lebedev and Lityagov, 1977 | DH |
Reaction thermochemistry data
Go To: Top, Condensed 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 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
+
= C16H16N4O2
By formula: C6H4N4O2 + C10H12 = C16H16N4O2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -151. | kJ/mol | Cm | Samuilov, Movchan, et al., 1985 | solid phase; solvent: Chlorobenzene |
+
= C16H17N3
By formula: C10H12 + C6H5N3 = C16H17N3
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -161. | kJ/mol | Cm | Samuilov, Movchan, et al., 1985 | solid phase; solvent: Chlorobenzene |
2 =
By formula: 2C5H6 = C10H12
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -195.1 | kJ/mol | Eqk | Lenz and Vaughan, 1989 | gas phase |
References
Go To: Top, Condensed phase thermochemistry data, 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.
Becker and Roth, 1934
Becker, G.; Roth, W.A.,
Verbrennungswarmen einiger cyclischer kohlenwasserstoffe,
Ber., 1934, 67, 627-632. [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]
Lebedev and Lityagov, 1977
Lebedev, B.V.; Lityagov, V.Ya.,
Thermodynamics of polypentenamer synthesis reactions,
Vysokomol. Soedin., 1977, B19, 558-560. [all data]
Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw,
Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2
. [all data]
Smirnova, Lebedev, et al., 1997
Smirnova, N.N.; Lebedev, B.V.; Kiparisova, E.G.; Makovetskii, K.L.; Ostrovskaya, I.Ya.,
Thermodynamics of endo- and exo-dicyclopentadienes, their metathesis and addition polymerizations, and the resulting polymers,
Poly. Sci., Ser. A, 1997, 39, 8, 893. [all data]
Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D.,
Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III,
J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985
. [all data]
Samuilov, Movchan, et al., 1985
Samuilov, Ya.D.; Movchan, A.I.; Solov'eva, S.E.; Konovalov, A.I.,
Thermochemical and kinetic study of 1,3-dipolar cycloadditions involving aryl azides and nitrones,
Zh. Org. Khim., 1985, 21, 1772-1776. [all data]
Lenz and Vaughan, 1989
Lenz, T.G.; Vaughan, J.D.,
Employing force-field calculations to predict equilibrium constants and other thermodynamic properties for the dimerization of 1,3-cyclopentadiene,
J. Phys. Chem., 1989, 93, 1592-1596. [all data]
Notes
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, References
- Symbols used in this document:
Cp,solid Constant pressure heat capacity of solid S°solid,1 bar Entropy of solid at standard conditions (1 bar) ΔHtrs Enthalpy of phase transition ΔStrs Entropy of phase transition ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔfusH Enthalpy of fusion ΔrH° Enthalpy of reaction at standard conditions ΔvapH Enthalpy of vaporization - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
- The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment. However, NIST makes no warranties to that effect, and NIST shall not be liable for any damage that may result from errors or omissions in the Database.
- Customer support for NIST Standard Reference Data products.