Lysine

• Formula: C₆H₁₄N₂O₂
• Molecular weight: 146.1876
• IUPAC Standard InChI: InChI=1S/C6H14N2O2/c7-4-2-1-3-5(8)6(9)10/h5H,1-4,7-8H2,(H,9,10)/t5-/m1/s1 Copy

  
• IUPAC Standard InChIKey: KDXKERNSBIXSRK-RXMQYKEDSA-N Copy
• CAS Registry Number: 56-87-1
• Chemical structure:
  This structure is also available as a 2d Mol file
• Species with the same structure:
  • L-Lysine, hydrate (1:1)
• Stereoisomers:
  • dl-Lysine
• Other names: L-Lysine; Lysine, L-; (S)-α,ε-Diaminocaproic acid; Hexanoic acid, 2,6-diamino-, (S)-; L-(+)-Lysine; Lysine acid; 2,6-Diaminohexanoic acid; α,ε-Diaminocaproic acid; L-H2N(CH2)4CH(NH2)COOH; Aminutrin; (S)-2,6-Diaminohexanoic acid; α-Lysine; (S)-Lysine; Lys; h-Lys-oh; L-Norleucine, 6-amino-
• Information on this page:
  • Condensed phase thermochemistry data
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • References
  • Notes
• Other data available:
  • Mass spectrum (electron ionization)
• Options:
  • Switch to calorie-based units

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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

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: 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

C₆H₁₃N₂O₂^- +  =

By formula: C₆H₁₃N₂O₂^- + H⁺ = C₆H₁₄N₂O₂

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
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard

Ionization energy determinations

De-protonation reactions

C₆H₁₃N₂O₂^- +  =

By formula: C₆H₁₃N₂O₂^- + H⁺ = C₆H₁₄N₂O₂

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.

Vasil'ev, Borodin, et al., 1991
Vasil'ev, V.P.; Borodin, V.A.; Kopnyshev, S.B., Calculation of the standard enthalpies of combustion and of formation of crystalline organic acids and complexones from the energy contributions of atomic groups, Russ. J. Phys. Chem. (Engl. Transl.), 1991, 65, 29-32. [all data]

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]

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]

Cannington and Ham, 1983
Cannington, P.H.; Ham, N.S., He(I) and He(II) photoelectron spectra of glycine and related molecules, J. Electron Spectrosc. Relat. Phenom., 1983, 32, 139. [all data]

Notes

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• Symbols used in this document:
  

  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
• The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment. However, NIST makes no warranties to that effect, and NIST shall not be liable for any damage that may result from errors or omissions in the Database.
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