Histidine

• Formula: C₆H₉N₃O₂
• Molecular weight: 155.1546
• IUPAC Standard InChI: InChI=1S/C6H9N3O2/c7-5(6(10)11)1-4-2-8-3-9-4/h2-3,5H,1,7H2,(H,8,9)(H,10,11)/t5-/m1/s1 Copy

  
• IUPAC Standard InChIKey: HNDVDQJCIGZPNO-RXMQYKEDSA-N Copy
• CAS Registry Number: 71-00-1
• Chemical structure:
  This structure is also available as a 2d Mol file
• Other names: L-Histidine; Histidine, L-; Glyoxaline-5-alanine; L-(-)-Histidine; 1H-Imidazole-4-propanoic acid, α-amino-, (S)-; 4-(2-Amino-2-carboxyethyl)imidazole; Anti-rheuma
• 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
  • IR Spectrum
  • References
  • Notes
• Other data available:
  • Condensed phase thermochemistry data
  • Phase change data
  • 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

C₆H₈N₃O₂^- +  =

By formula: C₆H₈N₃O₂^- + H⁺ = C₆H₉N₃O₂

 +  = ( • )

By formula: Na⁺ + C₆H₉N₃O₂ = (Na⁺ • C₆H₉N₃O₂)

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

C₆H₈N₃O₂^- +  =

By formula: C₆H₈N₃O₂^- + H⁺ = C₆H₉N₃O₂

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⁺ + C₆H₉N₃O₂ = (Na⁺ • C₆H₉N₃O₂)

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: Timothy J. Johnson, Tanya L. Myers, Yin-Fong Su, Russell G. Tonkyn, Molly Rose K. Kelly-Gorham, and Tyler O. Danby

Condensed Phase Spectrum

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Additional Data

References

Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR 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]

Bouchoux and Salpin, 2003
Bouchoux, G.; Salpin, J.Y., Gas-phase basicity of glycine, alanine, proline, serine, lysine, histidine and some of their peptides by the thermokinetic method, European J. Mass Spectrometry, 2003, 9, 391-402. [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]

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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