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 Copy

  
• IUPAC Standard InChIKey: HECLRDQVFMWTQS-BMNUFHGDSA-N Copy
• 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:
  • endo-Dicyclopentadiene
  • Dicyclopentadiene (endo)
  • Dicyclopentadiene, exo
  • endo-Dicyclopentadiene
• 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[5.2.1.0^2,6]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
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Phase change data
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • IR Spectrum
  • References
  • Notes
• Other data available:
  • Mass spectrum (electron ionization)
  • Gas Chromatography
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
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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

Enthalpy of vaporization

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

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 by: Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

View reactions leading to C₁₀H₁₂⁺ (ion structure unspecified)

Ionization energy determinations

IR Spectrum

Go To: Top, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, References, Notes

Data compiled by: Coblentz Society, Inc.

• LIQUID; Not specified, most likely a prism, grating, or hybrid spectrometer.; DIGITIZED BY NIST FROM HARD COPY; 4 cm^-1 resolution
• SOLUTION (10% CCl4 FOR 3800-1330, 10% CS2 FOR 1330-450 CM^-1); Not specified, most likely a prism, grating, or hybrid spectrometer.; DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 4 cm^-1 resolution

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

• gas

References

Go To: Top, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, 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]

Baker, Betteridge, et al., 1970
Baker, A.D.; Betteridge, D.; Kemp, N.R.; Kirby, R.E., Application of photoelectron spectrometry to pesticide analysis. Photoelectron spectra of fivemembered heterocycles and related molecules, Anal. Chem., 1970, 42, 1064. [all data]

Notes

Go To: Top, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, 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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