Proline
- Formula: C5H9NO2
- Molecular weight: 115.1305
- IUPAC Standard InChIKey: ONIBWKKTOPOVIA-SCSAIBSYSA-N
- CAS Registry Number: 147-85-3
- Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
The 3d structure may be viewed using Java or Javascript. - Stereoisomers:
- Other names: L-Proline; Proline, L-; (-)-(S)-Proline; L-(-)-Proline; 2-Pyrrolidinecarboxylic acid; 2-Pyrrolidinecarboxylic acid, (S)-
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Gas 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
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | -87.52 ± 0.96 | kcal/mol | Ccb | Sabbah and Laffitte, 1978 | see Sabbath and Laffitte, 1978 |
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
C5H8NO2- + =
By formula: C5H8NO2- + H+ = C5H9NO2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 340.2 ± 3.1 | kcal/mol | G+TS | O'Hair, Bowie, et al., 1992 | gas phase |
ΔrH° | 342.0 ± 2.2 | kcal/mol | CIDC | Jones, Bernier, et al., 2007 | gas phase |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 333.4 ± 3.0 | kcal/mol | CIDC | O'Hair, Bowie, et al., 1992 | gas phase |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Mass spectrum (electron ionization), References, Notes
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)
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Proton affinity (review) | 220.0 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 211.8 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Proton affinity at 298K
Proton affinity (kcal/mol) | Reference | Comment |
---|---|---|
221.3 ± 0.38 | Bouchoux and Salpin, 2003 | T = 298K; MM |
223.7 | Mezzache, Afonso, et al., 2003 | T = T(eff) = 315K; MM |
219.9 | Mirza, Prabhakar, et al., 2001 | T = T(eff) = 559-809K; Amino acids used as reference compounds. T(eff) at collision energies of 20 - 60 eV are 559-809 K.; MM |
224.4 | Bojesen and Breindahl, 1994 | PA increased by 2.0 kcal/mol for referencing values to Hunter and Lias, 1998; MM |
Gas basicity at 298K
Gas basicity (review) (kcal/mol) | Reference | Comment |
---|---|---|
214.1 ± 0.38 | Bouchoux and Salpin, 2003 | T = 298K; MM |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
8.3 | PE | Cannington and Ham, 1983 | LBLHLM |
9.36 | CTS | Slifkin and Allison, 1967 | RDSH |
9.0 | PE | Cannington and Ham, 1983 | Vertical value; LBLHLM |
De-protonation reactions
C5H8NO2- + =
By formula: C5H8NO2- + H+ = C5H9NO2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 340.2 ± 3.1 | kcal/mol | G+TS | O'Hair, Bowie, et al., 1992 | gas phase; B |
ΔrH° | 342.0 ± 2.2 | kcal/mol | CIDC | Jones, Bernier, et al., 2007 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 333.4 ± 3.0 | kcal/mol | CIDC | O'Hair, Bowie, et al., 1992 | gas phase; B |
Mass spectrum (electron ionization)
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, References, Notes
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
View image of digitized spectrum (can be printed in landscape orientation).
Due to licensing restrictions, this spectrum cannot be downloaded.
Owner | NIST Mass Spectrometry Data Center Collection (C) 2014 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
---|---|
Origin | Japan AIST/NIMC Database- Spectrum MS-NW-2505 |
NIST MS number | 228120 |
References
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Sabbah and Laffitte, 1978
Sabbah, R.; Laffitte, M.,
Thermodynamique de composes azotes. IV. Etude thermochimique de la sarcosine et de la L-proline,
Bull. Soc. Chim. Fr., 1978, 1, 50-52. [all data]
Sabbath and Laffitte, 1978
Sabbath, R.; Laffitte, M.,
Enthalpy of formation of solid L-proline,
J. Chem. Thermodyn., 1978, 10, 101-102. [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]
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]
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 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]
Mezzache, Afonso, et al., 2003
Mezzache, S.; Afonso, C.; Pepe, C.; Karoyan, P.; Fournier, F.; Tabet, J.C.,
Proton Affinity of Proline and Modified Prolines Using the Kinetic Method: Role of the Conformation Investigated by ab intio Calculations,
Rapid Comm. Mass Spectrometry, 2003, 17, 1626. [all data]
Mirza, Prabhakar, et al., 2001
Mirza, S.P.; Prabhakar, S.; Vairamani, M.,
Estimation of proton affinity of proline and tryptophan under electrospray ionization conditions using the extended kinetic method,
Rapid Comm. Mass Spectrometry, 2001, 15, 957. [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]
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]
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]
Notes
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), References
- Symbols used in this document:
ΔfH°gas Enthalpy of formation of gas 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
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