Tyrosine
- Formula: C9H11NO3
- Molecular weight: 181.1885
- IUPAC Standard InChI: InChI=1S/C9H11NO3/c10-8(9(12)13)5-6-1-3-7(11)4-2-6/h1-4,8,11H,5,10H2,(H,12,13)/t8-/m1/s1
- 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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Gas phase ion energetics data
Go To: Top, 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) | 221. | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
| Quantity | Value | Units | Method | Reference | Comment |
| Gas basicity | 213.2 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
De-protonation reactions
+
=
By formula: C9H10NO3- + H+ = C9H11NO3
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 340.6 ± 1.8 | kcal/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° | 337.7 ± 2.6 | kcal/mol | CIDC | Jones, Bernier, et al., 2007 | gas phase; B |
| ΔrH° | 337.6 ± 3.1 | kcal/mol | G+TS | O'Hair, Bowie, et al., 1992 | gas phase; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 332.5 ± 1.5 | kcal/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° | 329.5 ± 3.0 | kcal/mol | CIDC | O'Hair, Bowie, et al., 1992 | gas phase; B |
References
Go To: Top, 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.
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, Gas phase ion energetics data, References
- Symbols used in this document:
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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