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
  • Reaction thermochemistry data
  • Ion clustering data
  • Mass spectrum (electron ionization)
  • References
  • Notes
• Other data available:
  • Phase change data
  • IR Spectrum
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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

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: Robert C. Dunbar

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: Na⁺ + C₄H₆N₂O₂ = (Na⁺ • C₄H₆N₂O₂)

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)

Mass spectrum (electron ionization)

Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, Ion clustering 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: NIST Mass Spectrometry Data Center, William E. Wallace, director

Spectrum

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Additional Data

References

Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, Ion clustering data, Mass spectrum (electron ionization), Notes

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]

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

Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, Ion clustering data, Mass spectrum (electron ionization), 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)
  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

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