Tryptophan

• Formula: C₁₁H₁₂N₂O₂
• Molecular weight: 204.2252
• IUPAC Standard InChI: InChI=1S/C11H12N2O2/c12-9(11(14)15)5-7-6-13-10-4-2-1-3-8(7)10/h1-4,6,9,13H,5,12H2,(H,14,15) Copy

  
• IUPAC Standard InChIKey: QIVBCDIJIAJPQS-UHFFFAOYSA-N Copy
• CAS Registry Number: 54-12-6
• Chemical structure:
  This structure is also available as a 2d Mol file or as a computed 3d SD file
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• Stereoisomers:
  • L-Tryptophan
• Other names: DL-Tryptophan; DL-α-Amino-3-indolepropionic acid; DL-Trytophan; DL-Trytophane; Racemic Tryptophan; Tryptophan, DL-; Tryptophane; (.+/-.)-Tryptophan; NSC 13118; DL-Tryptophane
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• Information on this page:
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • Ion clustering data
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
  • References
  • Notes
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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

 +  =

By formula: C₁₁H₁₁N₂O₂^- + H⁺ = C₁₁H₁₂N₂O₂

 +  = ( • )

By formula: Na⁺ + C₁₁H₁₂N₂O₂ = (Na⁺ • C₁₁H₁₂N₂O₂)

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 compiled as indicated in comments:
B - John E. Bartmess
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

Ionization energy determinations

De-protonation reactions

 +  =

By formula: C₁₁H₁₁N₂O₂^- + H⁺ = C₁₁H₁₂N₂O₂

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⁺ + C₁₁H₁₂N₂O₂ = (Na⁺ • C₁₁H₁₂N₂O₂)

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

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, Mass spectrum (electron ionization), 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]

Gapeev and Dunbar, 2003
Gapeev, A.; Dunbar, R.C., Na+ Affinities of Gas-Phase Amino Acids by Ligand Exchange Equilibrium, Int. J. Mass Spectrom., 2003, 228, 2-3, 825, https://doi.org/10.1016/S1387-3806(03)00242-2 . [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]

Slifkin and Allison, 1967
Slifkin, M.A.; Allison, A.C., Measurement of ionization potentials from contact charge transfer spectra, Nature, 1967, 215, 949. [all data]

Akopyan and Loginov, 1967
Akopyan, M.E.; Loginov, Yy.V., Mass-spectrometric study of the phoionization of free α-aminoacids, High Energy Chem., 1967, 1, 83, In original 97. [all data]

McLean and Glese, 1950
McLean, D.G.; Glese, A.C., J. Biol. Chem., 1950, 187, 537. [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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