L-Asparagine

• Formula: C₄H₈N₂O₃
• Molecular weight: 132.1179
• IUPAC Standard InChI: InChI=1S/C4H8N2O3/c5-2(4(8)9)1-3(6)7/h2H,1,5H2,(H2,6,7)(H,8,9)/t2-/m1/s1 Copy

  
• IUPAC Standard InChIKey: DCXYFEDJOCDNAF-UWTATZPHSA-N Copy
• CAS Registry Number: 70-47-3
• Chemical structure:
  This structure is also available as a 2d Mol file or as a computed 3d SD file
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• Other names: Asparagine, L-; (-)-Asparagine; Agedoite; Altheine; Asparagine; Butanoic acid, 2,4-diamino-4-oxo-, (S)-; L-β-Asparagine; (S)-2,4-Diamino-4-oxobutanoic acid; Asn; Asparamide; Aspartic acid β amide; (S)-Asparagine; Asparagine acid; Aspartamic acid; Crystal VI; L-2,4-Diamino-4-oxobutanoic acid; NSC 82391; α-Aminosuccinamic acid; Asparagine l(-)
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • Ion clustering data
  • UV/Visible spectrum
  • References
  • Notes
• Other data available:
  • Condensed phase thermochemistry data
  • IR Spectrum
  • Mass spectrum (electron ionization)
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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:
B - John E. Bartmess
RCD - 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

C₄H₇N₂O₃^- +  =

By formula: C₄H₇N₂O₃^- + H⁺ = C₄H₈N₂O₃

 +  = ( • )

By formula: Na⁺ + C₄H₈N₂O₃ = (Na⁺ • C₄H₈N₂O₃)

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 as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias

Data compiled as indicated in comments:
B - John E. Bartmess
MM - Michael M. Meot-Ner (Mautner)

Proton affinity at 298K

Gas basicity at 298K

Protonation entropy at 298K

De-protonation reactions

C₄H₇N₂O₃^- +  =

By formula: C₄H₇N₂O₃^- + H⁺ = C₄H₈N₂O₃

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⁺ + C₄H₈N₂O₃ = (Na⁺ • C₄H₈N₂O₃)

UV/Visible 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: Victor Talrose, Alexander N. Yermakov, Alexy A. Usov, Antonina A. Goncharova, Axlexander N. Leskin, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina

Spectrum

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Additional Data

References

Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, UV/Visible spectrum, Notes

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

Jones, Bernier, et al., 2007
Jones, C.M.; Bernier, M.; Carson, E.; Colyer, K.E.; Metz, R.; Pawlow, A.; Wischow, E.D.; Webb, I.; Andriole, E.J.; Poutsma, J.C., Gas-phase Acities of the 20 Protein Amino Acids, Int. J. Mass Spectrom., 2007, 267, 1-3, 54-62, https://doi.org/10.1016/j.ijms.2007.02.018 . [all data]

O'Hair, Bowie, et al., 1992
O'Hair, R.J.; Bowie, J.H.; Gronert, S., Gas Phase Acidity of the alpha-Amino Acids, Int. J. Mass Spectrom. Ion Proc., 1992, 117, 23, https://doi.org/10.1016/0168-1176(92)80083-D . [all data]

Kish, Ohanessian, et al., 2003
Kish, M.M.; Ohanessian, G.; Wesdemiotis, C., The Na+ affinities of a-amino acids: side-chain substituent effects, Int. J. Mass Spectrom., 2003, 227, 3, 509, https://doi.org/10.1016/S1387-3806(03)00082-4 . [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]

Bouchoux, Buisson, et al., 2004
Bouchoux, G.; Buisson, D.A.; Colas, C.; Sablier, M., Protonation thermochemistry of alpha-amino acids bearing a basic residue, European J. Mass Spectrom., 2004, 10, 977. [all data]

Bojesen and Breindahl, 1994
Bojesen, G.; Breindahl, T., On the Proton Affinity od Some Alpha-Amino Acids and the Theory of the Kinetic Method., J. Chem. Soc. Perkin 2, 1994, 1029. [all data]

Saidel and Waldman, 1952
Saidel, L.J.; Waldman, S., J. Biol. Chem., 1952, 197, 285. [all data]

Notes

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• Symbols used in this document:
  

  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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