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
  • Reaction thermochemistry data
  • Ion clustering data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • References
  • Notes
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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

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)

IR Spectrum

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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: Coblentz Society, Inc.

Condensed Phase Spectrum

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Notice: Except where noted, spectra from this collection were measured on dispersive instruments, often in carefully selected solvents, and hence may differ in detail from measurements on FTIR instruments or in other chemical environments. More information on the manner in which spectra in this collection were collected can be found here.

Notice: Concentration information is not available for this spectrum and, therefore, molar absorptivity values cannot be derived.

Additional Data

Mass spectrum (electron ionization)

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

Spectrum

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Additional Data

References

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Ion clustering data, IR Spectrum, 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]

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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