Tyrosine
- Formula: C9H11NO3
- Molecular weight: 181.1885
- IUPAC Standard InChIKey: OUYCCCASQSFEME-MRVPVSSYSA-N
- CAS Registry Number: 60-18-4
- 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-Tyrosine; Tyrosine, L-; α-Amino-β-(4-hydroxyphenyl)propionic acid; (-)-α-Amino-p-hydroxyhydrocinnamic acid; p-Tyrosine; Benzenepropanoic acid, α-amino-4-hydroxy-, (S)-; L-p-Tyrosine; L-Phenylalanine, 4-hydroxy-; Propanoic acid, 2-amino-3-(4-hydroxyphenyl)-, (S)-; L-2-Amino-3-p-hydroxyphenylpropanoic acid; (S)-α-Amino-4-hydroxybenzenepropanoic acid; (S)-Tyrosine; NSC 82624
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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 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 |
---|---|---|---|---|---|
ΔfH°solid | -685.6 ± 1.5 | kJ/mol | Ccb | Huffman, Fox, et al., 1937 | Author's hf298=-165.54 kcal/mol; ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°solid | -4428.1 ± 1.5 | kJ/mol | Ccb | Huffman, Fox, et al., 1937 | Author's hf298=-165.54 kcal/mol; ALS |
ΔcH°solid | -4481.7 | kJ/mol | Ccb | Emery and Benedict, 1911 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°solid,1 bar | 214.01 | J/mol*K | N/A | Cole, Hutchens, et al., 1963 | DH |
S°solid,1 bar | 221.8 | J/mol*K | N/A | Huffman and Ellis, 1937 | Extrapolation below 90 K. 64.56 J/mol*K.; DH |
Constant pressure heat capacity of solid
Cp,solid (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
216.44 | 298.15 | Cole, Hutchens, et al., 1963 | DH |
214.30 | 294.6 | Huffman and Ellis, 1937 | T = 87 to 295 K. Value is unsmoothed experimental datum.; DH |
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:
HL - Edward P. Hunter and Sharon G. Lias
Data compiled as indicated in comments:
B - John E. Bartmess
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Proton affinity (review) | 926. | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 892.1 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
De-protonation reactions
By formula: C9H10NO3- + H+ = C9H11NO3
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1425. ± 7.5 | kJ/mol | G+TS | Tian, Wang, et al., 2009 | gas phase; Probes indicate 70% phenoxide, 30% carboxylate (0.5 kcal/mol). dSacid calc at B3LYP, mixture of anions; B |
ΔrH° | 1413. ± 11. | kJ/mol | CIDC | Jones, Bernier, et al., 2007 | gas phase; B |
ΔrH° | 1413. ± 13. | kJ/mol | G+TS | O'Hair, Bowie, et al., 1992 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1391. ± 6.3 | kJ/mol | N/A | Tian, Wang, et al., 2009 | gas phase; Probes indicate 70% phenoxide, 30% carboxylate (0.5 kcal/mol). dSacid calc at B3LYP, mixture of anions; B |
ΔrG° | 1379. ± 13. | kJ/mol | CIDC | O'Hair, Bowie, et al., 1992 | gas phase; B |
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.
Huffman, Fox, et al., 1937
Huffman, H.M.; Fox, S.W.; Ellis, E.L.,
Thermal data. VII. The heats of combustion of seven amino acids,
J. Am. Chem. Soc., 1937, 59, 2144-21. [all data]
Emery and Benedict, 1911
Emery, A.G.; Benedict, F.G.,
The heat of combustion of compounds of physiological importance,
Am. J. Physiol., 1911, 28, 301-307. [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 Ellis, 1937
Huffman, H.M.; Ellis, E.L.,
Thermal data. VIII. The heat capacities, entropies and free energies of some amino acids,
J. Am. Chem. Soc., 1937, 59, 2150-2152. [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]
Tian, Wang, et al., 2009
Tian, Z.X.; Wang, X.B.; Wang, L.S.; Kass, S.R.,
Are Carboxyl Groups the Most Acidic Sites in Amino Acids? Gas-Phase Acidities, Photoelectron Spectra, and Computations on Tyrosine, p-Hydroxybenzoic Acid, and Their Conjugate Bases,
J. Am. Chem. Soc., 2009, 131, 3, 1174-1181, https://doi.org/10.1021/ja807982k
. [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]
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]
Notes
Go To: Top, Condensed phase thermochemistry data, Gas phase ion energetics data, References
- Symbols used in this document:
Cp,solid Constant pressure heat capacity of solid S°solid,1 bar Entropy of solid at standard conditions (1 bar) ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔfH°solid Enthalpy of formation of solid 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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