dl-Proline

• Formula: C₅H₉NO₂
• Molecular weight: 115.1305
• IUPAC Standard InChI: InChI=1S/C5H9NO2/c7-5(8)4-2-1-3-6-4/h4,6H,1-3H2,(H,7,8) Copy

  
• IUPAC Standard InChIKey: ONIBWKKTOPOVIA-UHFFFAOYSA-N Copy
• CAS Registry Number: 609-36-9
• Chemical structure:
  This structure is also available as a 2d Mol file
• Stereoisomers:
  • Proline
• Other names: 2-Pyrrolidine carboxylic acid; Proline, DL-
• 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
  • References
  • Notes
• Other data available:
  • Ion clustering data
  • Mass spectrum (electron ionization)
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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 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 as indicated in comments:
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
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

C₅H₁₀NO₂⁺ +  = (C₅H₁₀NO₂⁺ • )

By formula: C₅H₁₀NO₂⁺ + C₅H₉NO₂ = (C₅H₁₀NO₂⁺ • C₅H₉NO₂)

 +  = ( • )

By formula: Na⁺ + C₅H₉NO₂ = (Na⁺ • C₅H₉NO₂)

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.

Ponomarev and Migarskaya, 1960
Ponomarev, V.V.; Migarskaya, L.B., Heats of combustion of some amino-acids, Russ. J. Phys. Chem. (Engl. Transl.), 1960, 34, 1182-1183. [all data]

Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]

Meot-Ner, Hunter, et al., 1979
Meot-Ner, (Mautner); Hunter, E.P.; Field, F.H., Ion Thermochemistry of Low Volatility Compounds in the Gas Phase. I. Intrinsic Basicities of Alpha - Amino Acids, J. Am. Chem. Soc., 1979, 101, 3, 686, https://doi.org/10.1021/ja00497a034 . [all data]

Meot-Ner and Field, 1974
Meot-Ner, (Mautner); Field, F.H., Solvation and Association of Protonated Gaseous Amino Acids, J. Am. Chem. Soc., 1974, 96, 10, 3168, https://doi.org/10.1021/ja00817a024 . [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]

Notes

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• Symbols used in this document:
  

  ΔcH°solid	Enthalpy of combustion of solid at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔrS°	Entropy of reaction at standard conditions

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