Proline

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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
Δfgas-87.52 ± 0.96kcal/molCcbSabbah and Laffitte, 1978see Sabbath and Laffitte, 1978

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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity Value Units Method Reference Comment
Δfsolid-121.3 ± 0.62kcal/molCcbVasilev, Borodin, et al., 1989Uc =-2744.77 kJ/mol; ALS
Δfsolid-123.13 ± 0.12kcal/molCcbSabbath and Laffitte, 1978ALS
Quantity Value Units Method Reference Comment
Δcsolid-656.36 ± 0.60kcal/molCcbVasilev, Borodin, et al., 1989Uc =-2744.77 kJ/mol; ALS
Δcsolid-654.54 ± 0.1kcal/molCcbSabbath and Laffitte, 1978ALS
Quantity Value Units Method Reference Comment
solid,1 bar39.211cal/mol*KN/ACole, Hutchens, et al., 1963DH
solid,1 bar40.80cal/mol*KN/AHuffman and Fox, 1940Extrapolation below 90 K, 56.07 J/mol*K.; DH

Constant pressure heat capacity of solid

Cp,solid (cal/mol*K) Temperature (K) Reference Comment
35.95298.15Spink and Wads, 1975DH
36.130298.15Cole, Hutchens, et al., 1963T = 11 to 305 K.; DH
35.641300.4Huffman and Fox, 1940T = 90 to 298 K. Value is unsmoothed experimental datum.; DH

Phase change 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:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos

Quantity Value Units Method Reference Comment
Δsub35.6 ± 0.5kcal/molCSabbah and Laffitte, 1978see Sabbath and Laffitte, 1978; ALS

Enthalpy of sublimation

ΔsubH (kcal/mol) Temperature (K) Method Reference Comment
30.4 ± 0.2406.TE,MEde Kruif, Voogd, et al., 1979Based on data from 396. to 416. K.; AC
35.6 ± 1.400.CSabbah and Laffite, 1978Based on data from 380. to 420. K.; AC
23.1 ± 0.2455.VSvec and Clyde, 1965ALS

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- + Hydrogen cation = Proline

By formula: C5H8NO2- + H+ = C5H9NO2

Quantity Value Units Method Reference Comment
Δr340.2 ± 3.1kcal/molG+TSO'Hair, Bowie, et al., 1992gas phase
Δr342.0 ± 2.2kcal/molCIDCJones, Bernier, et al., 2007gas phase
Quantity Value Units Method Reference Comment
Δr333.4 ± 3.0kcal/molCIDCO'Hair, Bowie, et al., 1992gas phase

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)
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)220.0kcal/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity211.8kcal/molN/AHunter and Lias, 1998HL

Proton affinity at 298K

Proton affinity (kcal/mol) Reference Comment
221.3 ± 0.38Bouchoux and Salpin, 2003T = 298K; MM
223.7Mezzache, Afonso, et al., 2003T = T(eff) = 315K; MM
219.9Mirza, Prabhakar, et al., 2001T = T(eff) = 559-809K; Amino acids used as reference compounds. T(eff) at collision energies of 20 - 60 eV are 559-809 K.; MM
224.4Bojesen and Breindahl, 1994PA 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 ± 0.38Bouchoux and Salpin, 2003T = 298K; MM

Ionization energy determinations

IE (eV) Method Reference Comment
8.3PECannington and Ham, 1983LBLHLM
9.36CTSSlifkin and Allison, 1967RDSH
9.0PECannington and Ham, 1983Vertical value; LBLHLM

De-protonation reactions

C5H8NO2- + Hydrogen cation = Proline

By formula: C5H8NO2- + H+ = C5H9NO2

Quantity Value Units Method Reference Comment
Δr340.2 ± 3.1kcal/molG+TSO'Hair, Bowie, et al., 1992gas phase; B
Δr342.0 ± 2.2kcal/molCIDCJones, Bernier, et al., 2007gas phase; B
Quantity Value Units Method Reference Comment
Δr333.4 ± 3.0kcal/molCIDCO'Hair, Bowie, et al., 1992gas phase; B

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

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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

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References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change 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]

Vasilev, Borodin, et al., 1989
Vasilev, V.P.; Borodin, V.A.; Kopnyshev, S.B., Standard enthalpies of formation of L-histidine and L-proline, Russ. J. Phys. Chem. (Engl. Transl.), 1989, 63, 891-892. [all data]

Cole, Hutchens, et al., 1963
Cole, A.G.; Hutchens, J.O.; Stout, J.W., Heat capacities from 11 to 305°K. and entropies of L-phenylalanine, L-proline, L-tryptophane, and L-tyrosine. Some free energies of formation, J. Phys. Chem., 1963, 67, 1852-1855. [all data]

Huffman and Fox, 1940
Huffman, H.M.; Fox, S.W., Thermal data. XIII. The heat capacities and entropies of creatine hydrate, DL-citrulline, DL-ornithine, L-proline and taurine, J. Am. Chem. Soc., 1940, 62, 3464-3465. [all data]

Spink and Wads, 1975
Spink, C.H.; Wads, I., Thermochemistry of solutions of biochemical model compounds. 4. The partial molar heat capacities of some amino acids in aqueous solution, J. Chem. Thermodynam., 1975, 7, 561-572. [all data]

de Kruif, Voogd, et al., 1979
de Kruif, C.G.; Voogd, J.; Offringa, J.C.A., Enthalpies of sublimation and vapour pressures of 14 amino acids and peptides, The Journal of Chemical Thermodynamics, 1979, 11, 7, 651-656, https://doi.org/10.1016/0021-9614(79)90030-2 . [all data]

Sabbah and Laffite, 1978
Sabbah, R.; Laffite, M., Bull. Soc. Chim. Fr., 1978, 1, 50. [all data]

Svec and Clyde, 1965
Svec, H.J.; Clyde, D.D., Vapor pressures of some α-amino acids, J. Chem. Eng. Data, 1965, 10, 151. [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, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), References