2,5-Piperazinedione

• Formula: C₄H₆N₂O₂
• Molecular weight: 114.1026
• IUPAC Standard InChI: InChI=1S/C4H6N2O2/c7-3-1-5-4(8)2-6-3/h1-2H2,(H,5,8)(H,6,7) Copy

  
• IUPAC Standard InChIKey: BXRNXXXXHLBUKK-UHFFFAOYSA-N Copy
• CAS Registry Number: 106-57-0
• 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: Cyclo(glycylglycyl); Cyclic(glycylglycyl); α,γ-Diacipiperazine; Cyclodiglycine; Cycloglycylglycine; Diglycolyl diamide; Diketopiperazine; Glycine, bimol. cyclic peptide; Glycine, N-glycyl-, cyclic peptide; Glycylglycine lactam; 2,5-Diketopiperazine; 2,5-Dioxopiperazine; Piperazine-2,5-dione; NSC 26345
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Condensed phase thermochemistry data
  • Phase change data
  • Ion clustering data
  • References
  • Notes
• Other data available:
  • Reaction thermochemistry data
  • IR Spectrum
  • Mass spectrum (electron ionization)
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• NIST / TRC Web Thermo Tables, professional edition (thermophysical and thermochemical data)

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Condensed 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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing

Constant pressure heat capacity of solid

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: William E. Acree, Jr., James S. Chickos

Enthalpy of sublimation

Ion clustering 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 C. Dunbar

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. Searches may be limited to ion clustering reactions. A general reaction search form is also available.

Clustering reactions

 +  = ( • )

By formula: Na⁺ + C₄H₆N₂O₂ = (Na⁺ • C₄H₆N₂O₂)

References

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Lebedev, Kulagina, et al., 1982
Lebedev, B.V.; Kulagina, T.G.; Kiparisova, E.G., Thermodynamics of dl-lactide, ethylene oxalate, and 2,5-dioxopiperazine in the range 0-330 K., Russ. J. Phys. Chem. (Engl. Transl.), 1982, 56, 1641-1643. [all data]

Lebedev, Kulagina, et al., 1981
Lebedev, B.V.; Kulagina, T.G.; Kiparisova, E.G., Thermodynamics of 2,5-piperazinedione in the range 0-330 K, J. Gen. Chem. USSR, 1981, 51, 174-177. [all data]

Wrede, 1911
Wrede, F., Uber die Bestimmung von Berbrennungswarmen mittels der kalorimetrischen Bombe unter Benutzung des Platinwiderstandsthermometers, Z. Phys. Chem. (Leipzig), 1911, 81-94. [all data]

Fischer and Wrede, 1904
Fischer, E.; Wrede, F., Uber die Verbrennungswarme einiger organischer Verbindungen, Sitzungsber. Dtsch. Akad. Wiss. Berlin Kl. Math. Phys. Tech., 1904, 687-715. [all data]

Lemoult, 1904
Lemoult, M.P., Remarques sur une serie recenie de determinations calorimetriques, Compt. Rend., 1904, 663-635. [all data]

Lebedev, Kulagina, et al., 1982, 2
Lebedev, B.V.; Kulagina, T.G.; Kiparisova, Y.G., Thermodynamics of dl-lactide, ethylene oxalate, and 2,5-dioxopiperazine in the range 0-330 K, Zhur. Fiz. Khim., 1982, 56, 2665-2669. [all data]

Lebedev, Kulagina, et al., 1981, 2
Lebedev, B.V.; Kulagina, T.G.; Kiparisova, Y.G., Thermodynamics of 2,5-diketopiperazine in the 0-330K range, Zhur. Obshch. Khim., 1981, 51, 199-203. [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]

Cerda, Hoyau, et al., 1998
Cerda, B.A.; Hoyau, S.; Ohanessian, G.; Wesdemiotis, C., PAs of Peptides, J. Am. Chem. Soc., 1998, 120, 2437. [all data]

Notes

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• 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)
  ΔcH°solid	Enthalpy of combustion of solid at standard conditions
  ΔfH°solid	Enthalpy of formation of solid at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔsubH	Enthalpy of sublimation

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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