Carbic anhydride

• Formula: C₉H₈O₃
• Molecular weight: 164.1580
• IUPAC Standard InChI: InChI=1S/C9H8O3/c10-8-6-4-1-2-5(3-4)7(6)9(11)12-8/h1-2,4-7H,3H2/t4-,5-,6-,7+/m0/s1 Copy

  
• IUPAC Standard InChIKey: KNDQHSIWLOJIGP-ZTYPAOSTSA-N Copy
• CAS Registry Number: 129-64-6
• 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:
  • (1α,2α,3β,6β)-1,2,3,6-tetrahydro-3,6-methanophthalic anhydride
• Other names: (3aα,4α,7α,7aα)-3a,4,7,7a-Tetrahydro-4,7-methano-isobenzofuran-1,3-dione; 4,7-Methanoisobenzofuran-1,3-dione, 3a,4,7,7a-tetrahydro-, (3aα,4α,7α,7aα)-; 8,9,10-Trinorborn-5-ene-2,3-dicarboxylic anhydride; endo-Himic acid anhydride; endo-3,6-Methylene-1,2,3,6-tetrahydrophthalic anhydride; endo-5-Norbornene-2,3-dicarboxylic anhydride; endo,cis-5-Norbornene-2,3-dicarboxylic anhydride; Endic anhydride; Nadic anhydride; 3,6-Endomethylene-δ4-tetrahydrophthalic anhydride; 5-Norbornene-endo-2,3-dicarboxylic anhydride; 5-Norbornene-2,3-dicarboxylic anhydride, cis-endo-; 4,7-Methanoisobenzofuran-1,3-dione, 3a,4,7,7a-tetrahydro-, (3aR,4S,7R,7aS)-rel-; Bicyclo[2.2.1hept-5-ene-2-endo,3-endo-dicarboxylic anhydride; Bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid endo-cis-anhydride; cis-5-Norbornene-endo-2,3-dicarboxylic anhydride; NSC 102277
• 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
  • References
  • Notes
• Other data available:
  • Mass spectrum (electron ionization)
• Options:
  • Switch to SI units

Data at NIST subscription sites:

• NIST / TRC Web Thermo Tables, professional edition (thermophysical and thermochemical data)

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.

Phase change data

Go To: Top, 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:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos

Enthalpy of fusion

Reaction thermochemistry data

Go To: Top, 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

 +  =

By formula: C₄H₂O₃ + C₅H₆ = C₉H₈O₃

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.

Weinstein, Leffler, et al., 1984
Weinstein, D.I.; Leffler, A.J.; Currie, J.A., Phase Transitions in Bicyclic Compounds, Mol. Cryst. Liq. Cryst., 1984, 104, 95. [all data]

Rogers and Quan, 1973
Rogers, F.E.; Quan, S.W., Thermochemistry of the Diels-Alder reaction. III. Heat of addition of cyclopentadience to maleic anhydride, J. Phys. Chem., 1973, 77, 828-831. [all data]

Pedley and Rylance, 1977
Pedley, J.B.; Rylance, J., , Computer Analysed Thermochemical Data: Organic and Organometallic Compounds, University of Sussex, Brighton, 1977. [all data]

Pincock, Wilson, et al., 1967
Pincock, Richard E.; Wilson, Keith R.; Kiovsky, Thomas E., Thermal isomerization in polycrystalline exo- and endo-5-norbornene-2,3-dicarboxylic anhydrides, J. Am. Chem. Soc., 1967, 89, 26, 6890-6897, https://doi.org/10.1021/ja01002a015 . [all data]

Breslauer and Kabakoff, 1974
Breslauer, K.J.; Kabakoff, D.S., Enthalpy of the Diels-Alder reaction of cyclopentadiene and maleic anhydride, J. Org. Chem., 1974, 39, 721-722. [all data]

Notes

Go To: Top, Phase change data, Reaction thermochemistry data, References

• Symbols used in this document:
  

  Ttriple	Triple point temperature
  ΔfusH	Enthalpy of fusion
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔsubH°	Enthalpy of sublimation at standard conditions

• 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.