DL-Phenylalanine
- Formula: C9H11NO2
- Molecular weight: 165.1891
- IUPAC Standard InChI: InChI=1S/C9H11NO2/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-5,8H,6,10H2,(H,11,12)
- IUPAC Standard InChIKey: COLNVLDHVKWLRT-UHFFFAOYSA-N
- CAS Registry Number: 150-30-1
- 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: DL-β-Phenylalanine; β-Phenylalanine, dl-; (.+/-.)-Phenylalanine; Alanine, phenyl-, DL-; DL-α-Amino-β-phenylpropionic acid; DL-β-Phenyl-α-alanine; DL-2-Amino-3-phenylpropanoic acid; DL-3-Phenylalanine; DLPA; 2-Amino-3-phenylpropionic acid, dl-; NSC 9959; Phenylalanine; L-Phenylalanine
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Condensed phase thermochemistry data
Go To: Top, 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: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°solid | -460.6 ± 2.6 | kJ/mol | Ccb | Breitenbach, Derkosch, et al., 1952 | Reanalyzed by Cox and Pilcher, 1970, Original value = -459.0 kJ/mol |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°solid | -4653.0 ± 2.5 | kJ/mol | Ccb | Breitenbach, Derkosch, et al., 1952 | Reanalyzed by Cox and Pilcher, 1970, Original value = -4653.9 kJ/mol |
| ΔcH°solid | -4664.3 | kJ/mol | Ccb | Fischer and Wrede, 1904 | Heat of combustion corrected for pressure |
Gas phase ion energetics data
Go To: Top, Condensed phase thermochemistry 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:
L - Sharon G. Lias
Data compiled as indicated in comments:
LL - Sharon G. Lias and Joel F. Liebman
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 |
|---|---|---|---|---|---|
| IE (evaluated) | 8.4 | eV | N/A | N/A | L |
Ionization energy determinations
| IE (eV) | Method | Reference | Comment |
|---|---|---|---|
| 8.5 | PE | Campbell, Marzluff, et al., 1994 | LL |
| 8.4 | PE | Cannington and Ham, 1983 | LBLHLM |
| ≤8.4 | PI | Akopyan and Loginov, 1967 | RDSH |
| 8.9 | PE | Campbell, Marzluff, et al., 1994 | Vertical value; LL |
| 9.4 | PE | Cannington and Ham, 1983 | Vertical value; LBLHLM |
References
Go To: Top, Condensed phase thermochemistry 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.
Breitenbach, Derkosch, et al., 1952
Breitenbach, J.W.; Derkosch, J.; Wessely, F.,
Energetik der bildung hochmolekularer polypeptide,
Monatsh. Chem., 1952, 83, 591. [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]
Fischer and Wrede, 1904
Fischer, E.; Wrede, F.,
Uber die Verbrennungswarme einiger organischer Verbindungen,
Sitzungsber. Dtsch. Akad. Wiss. Berlin Kl. Math. Phys. Tech., 1904, 687-715. [all data]
Campbell, Marzluff, et al., 1994
Campbell, S.; Marzluff, E.M.; Rodgers, M.T.; Beauchamp, J.L.; Rempe, M.E.; Schwinck, K.F.; Lichtenberger, D.L.,
Proton affinities and photoelectron spectra of phenylalanine and N-methyl and N,N-dimethylphenylalanine. Correlation of lone pair ionization energies with proton affinities and implications for N-methylation as a method to effect site specific protonation of peptides,
J. Am. Chem. Soc., 1994, 116, 5257. [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]
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]
Notes
Go To: Top, Condensed phase thermochemistry data, Gas phase ion energetics data, References
- Symbols used in this document:
IE (evaluated) Recommended ionization energy ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔfH°solid Enthalpy of formation of solid at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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