N-Glycylglycine

• Formula: C₄H₈N₂O₃
• Molecular weight: 132.1179
• IUPAC Standard InChI: InChI=1S/C4H8N2O3/c5-1-3(7)6-2-4(8)9/h1-2,5H2,(H,6,7)(H,8,9) Copy

  
• IUPAC Standard InChIKey: YMAWOPBAYDPSLA-UHFFFAOYSA-N Copy
• CAS Registry Number: 556-50-3
• Chemical structure:
  This structure is also available as a 2d Mol file
• Other names: Glycine, N-glycyl-; Diglycine; Glycylglycine; Glycine dipeptide
• 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
  • Gas phase ion energetics data
  • References
  • Notes
• Other data available:
  • Ion clustering data
  • Mass spectrum (electron ionization)
• Options:
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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 as indicated in comments:
RCD - Robert C. Dunbar
B - John E. Bartmess

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⁺ + C₄H₈N₂O₃ = (Na⁺ • C₄H₈N₂O₃)

Free energy of reaction

CAS Reg. No. 23372-53-4 +  = C₈H₁₅N₄O₆^-

By formula: CAS Reg. No. 23372-53-4 + C₄H₈N₂O₃ = C₈H₁₅N₄O₆^-

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 evaluated by: Edward P. Hunter and Sharon G. Lias

References

Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Notes

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

Diaz, Domalski, et al., 1992
Diaz, E.L.; Domalski, E.S.; Colbert, J.C., Enthalpies of combustion of glycylglycine and DL-alanyl-DL-alamine, J. Chem. Thermodyn., 1992, 24, 1311-1318. [all data]

Huffman, 1942
Huffman, H.M., Thermal data. XV. The heats of combustion and free energies of some compounds containing the peptide bond, J. Phys. Chem., 1942, 46, 885-891. [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]

Hutchens, Cole, et al., 1969
Hutchens, J.O.; Cole, A.G.; Stout, J.W., Heat capacities from 11 to 305°K, entropies and free energy of formation of glycylglycine, J. Biol. Chem., 1969, 244, 33-35. [all data]

Huffman, 1941
Huffman, H.M., Thermal data. XIV. The heat capacities and entropies of some compounds having the peptide bond, J. Am. Chem. Soc., 1941, 63, 688-689. [all data]

Badelin, Kulikov, et al., 1990
Badelin, V.G.; Kulikov, O.V.; Batagin, V.S.; Udzig, E.; Zielenkiewicz, A.; Zielenkiewicz, W.; Krestov, G.A., Physico-chemical properties of peptides and their solutions, Thermochim. Acta, 1990, 169, 81-93. [all data]

Kulikov, Kozlov, et al., 1989
Kulikov, O.V.; Kozlov, V.A.; Malenkina, L.I.; Badelin, V.G., Heat capacities of amino acids and peptides and excess characteristics ot their aqueous solutions, Sbornik Nauch. Trud., Termodin. Rast. neelect., Ivanovo, Inst. nevod. rast., 1989, Akad. [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]

Klassen, Anderson, et al., 1996
Klassen, J.S.; Anderson, S.G.; Blades, A.T.; Kebarle, P., Reaction Enthalpies for M+L = M+ + L, Where M+ = Na+ and K+ and L = Acetamide, N-Methylacetamide, N,N-Dimethylacetamide, Glycine, and Glycylglycine, from Determinations of the Collision-Induced Dissociation Thresholds, J. Phys. Chem., 1996, 100, 33, 14218, https://doi.org/10.1021/jp9608382 . [all data]

Feng, Gronert, et al., 1999
Feng, W.Y.; Gronert, S.; Lebrilla, C.B., Lithium and sodium ion binding energies of N-acetyl and N-glycyl amino acids, J. Am. Chem. Soc., 1999, 121, 6, 1365, https://doi.org/10.1021/ja983116s . [all data]

Liu, Wyttenbacj, et al., 2004
Liu, D.; Wyttenbacj, T.; Carpenter, C.J.; Bowers, M.T., Investigation of Non-Covalent Interactions in Deprotonated Peptides: Structural and Energetic Competition between Aggregation and Hydration, J. Am. Chem. Soc., 2004, 126, 10, 3261, https://doi.org/10.1021/ja0393628 . [all data]

Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G., Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update, J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018 . [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)
  T	Temperature
  ΔcH°solid	Enthalpy of combustion of solid at standard conditions
  ΔfH°solid	Enthalpy of formation of solid at standard conditions
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions

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