Alanine

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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
Δsub34.6 ± 1.0kcal/molCNgauv, Sabbah, et al., 1977ALS
Δsub34.6 ± 1.0kcal/molN/ANguon Ngauv, Sabbah, et al., 1977AC

Enthalpy of sublimation

ΔsubH (kcal/mol) Temperature (K) Method Reference Comment
31.7 ± 0.2414.TE,MEde Kruif, Voogd, et al., 1979AC
31.64 ± 0.31433.CNguon Ngauv, Sabbah, et al., 1977Based on data from 413. to 450. K.; AC
33.0 ± 0.2455.VSvec and Clyde, 1965ALS

Gas phase ion energetics data

Go To: Top, Phase change data, 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
L - Sharon G. Lias

Data compiled as indicated in comments:
B - John E. Bartmess
MM - Michael M. Meot-Ner (Mautner)
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

Quantity Value Units Method Reference Comment
IE (evaluated)8.88eVN/AN/AL
Quantity Value Units Method Reference Comment
Proton affinity (review)215.5kcal/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity207.4kcal/molN/AHunter and Lias, 1998HL

Proton affinity at 298K

Proton affinity (kcal/mol) Reference Comment
213.8 ± 0.1Bouchoux and Salpin, 2003T = 298K; MM
215.6 ± 1.Hahn and Wesdemiotis, 2003MM

Gas basicity at 298K

Gas basicity (review) (kcal/mol) Reference Comment
206.8 ± 0.1Bouchoux and Salpin, 2003T = 298K; MM
206.5 ± 1.5Cassady, Carr, et al., 1995T = 298K; GB> dimethylformamide, ≈ 3-methylaniline, < 3-fluropyridine; MM
206.4 ± 1.6Wu and Lebrilla, 1995T = 300K; MM

Ionization energy determinations

IE (eV) Method Reference Comment
8.88PEKlasinc, 1976LLK
8.8PEDebies and Rabalais, 1974LLK
9.63CTSSlifkin and Allison, 1967RDSH

De-protonation reactions

C3H6NO2- + Hydrogen cation = Alanine

By formula: C3H6NO2- + H+ = C3H7NO2

Quantity Value Units Method Reference Comment
Δr341.8 ± 1.9kcal/molCIDCJones, Bernier, et al., 2007gas phase; B
Δr340.7 ± 2.1kcal/molG+TSLocke and McIver, 1983gas phase; B
Quantity Value Units Method Reference Comment
Δr334.8 ± 2.0kcal/molH-TSJones, Bernier, et al., 2007gas phase; B
Δr333.7 ± 2.0kcal/molIMRELocke and McIver, 1983gas phase; B

References

Go To: Top, Phase change data, Gas phase ion energetics data, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Ngauv, Sabbah, et al., 1977
Ngauv, S.N.; Sabbah, R.; Laffitte, M., Thermodynamique de composes azotes. III. Etude thermochimique de la glycine et de la l-α-alanine, Thermochim. Acta, 1977, 20, 371-380. [all data]

Nguon Ngauv, Sabbah, et al., 1977
Nguon Ngauv, Song; Sabbah, Raphael; Laffitie, Marc, Thermodynamique de composes azotes III. Etude Thermochimique de la glycine et de la l-α-alanine, Thermochimica Acta, 1977, 20, 3, 371-380, https://doi.org/10.1016/0040-6031(77)85091-0 . [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]

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]

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]

Hahn and Wesdemiotis, 2003
Hahn, I.S.; Wesdemiotis, C., Protonation Thermochemistry of beta-Alanine. An Evaluation of Proton Affinities and Entropies Determined by the Extended Kinetic Method, Int. J. Mass Spectrometry, 2003, 222, 465. [all data]

Cassady, Carr, et al., 1995
Cassady, C.J.; Carr, S.R.; Zhang, K.; Chung-Phillips, C., Experimental and Ab Intio Studies of Protonations of Alanine and Samll Peptides of Alanine and Glycine, J. Org. Chem., 1995, 60, 1704. [all data]

Wu and Lebrilla, 1995
Wu, J.; Lebrilla, C.B., Intrinsic Basicity of Oligomeric Peptides that Contain Glycine, Alanine, and Valine - The Effects of the Alkyl Side Chain on Proton Transfer Reactions, J. Am. Soc. Mass Spectrom., 1995, 6, 91. [all data]

Klasinc, 1976
Klasinc, L., Application of photoelectron spectroscopy to biologically active molecules and their constituent parts, J. Electron Spectrosc. Relat. Phenom., 1976, 8, 161. [all data]

Debies and Rabalais, 1974
Debies, T.P.; Rabalais, J.W., Electronic structure of amino acids and ureas, J. Electron Spectrosc. Relat. Phenom., 1974, 3, 315. [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]

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]

Locke and McIver, 1983
Locke, M.J.; McIver, R.T., Jr., Effect of Solvation on the Acid/Base Properties of Glycine, J. Am. Chem. Soc., 1983, 105, 4226. [all data]


Notes

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