Valine
- Formula: C5H11NO2
- Molecular weight: 117.1463
- IUPAC Standard InChIKey: KZSNJWFQEVHDMF-SCSAIBSYSA-N
- CAS Registry Number: 72-18-4
- Chemical structure:
This structure is also available as a 2d Mol file - Stereoisomers:
- Other names: L-Valine; Valine, L-; Butanoic acid, 2-amino-3-methyl-; Butanoic acid, 2-amino-3-methyl-, (S)-; L-(+)-α-Aminoisovaleric acid; 2-Amino-3-methylbutanoic acid; 2-Amino-3-methylbutyric acid; L-iso-C3H7CH(NH2)COOH; (S)-2-Amino-3-methylbutanoic acid; (S)-2-Amino-3-methylbutyric acid; (S)-Valine; NSC 76038
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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 |
---|---|---|---|---|---|
ΔfH°solid | -628.9 ± 1.9 | kJ/mol | Ccb | Vasil'ev, Borodin, et al., 1991 | ALS |
ΔfH°solid | -618.0 | kJ/mol | Ccb | Hutchens, Cole, et al., 1963 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°solid | -2910.7 ± 1.9 | kJ/mol | Ccb | Vasil'ev, Borodin, et al., 1991 | ALS |
ΔcH°solid | -2920.1 ± 0.54 | kJ/mol | Ccb | Tsuzuki and Hunt, 1957 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°solid,1 bar | 178.87 | J/mol*K | N/A | Hutchens, Cole, et al., 1963 | DH |
Constant pressure heat capacity of solid
Cp,solid (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
168.5 | 298.15 | Spink and Wads, 1975 | DH |
168.82 | 298.15 | Hutchens, Cole, et al., 1963 | T = 11 to 310 K.; 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
Enthalpy of sublimation
ΔsubH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
163. ± 0.8 | 455. | V | Svec and Clyde, 1965 | ALS |
163. ± 8. | 455. | ME | Svec and Clyde, 1965, 2 | See also Clyde and Svec, 1964 and Chiarelli and Gross, 1989.; AC |
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
C5H10NO2- + =
By formula: C5H10NO2- + H+ = C5H11NO2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1431. ± 7.9 | kJ/mol | CIDC | Jones, Bernier, et al., 2007 | gas phase |
ΔrH° | 1420. ± 13. | kJ/mol | G+TS | O'Hair, Bowie, et al., 1992 | gas phase |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1391. ± 13. | kJ/mol | CIDC | O'Hair, Bowie, et al., 1992 | gas 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)
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Proton affinity (review) | 910.6 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 876.7 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Gas basicity at 298K
Gas basicity (review) (kJ/mol) | Reference | Comment |
---|---|---|
873. ± 3. | Wu and Lebrilla, 1995 | T = 300K; MM |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
8.71 | PE | Klasinc, 1976 | LLK |
De-protonation reactions
C5H10NO2- + =
By formula: C5H10NO2- + H+ = C5H11NO2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1431. ± 7.9 | kJ/mol | CIDC | Jones, Bernier, et al., 2007 | gas phase; B |
ΔrH° | 1420. ± 13. | kJ/mol | G+TS | O'Hair, Bowie, et al., 1992 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1391. ± 13. | kJ/mol | CIDC | O'Hair, Bowie, et al., 1992 | gas phase; B |
IR Spectrum
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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: Coblentz Society, Inc.
Condensed Phase Spectrum
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Notice: Except where noted, spectra from this collection were measured on dispersive instruments, often in carefully selected solvents, and hence may differ in detail from measurements on FTIR instruments or in other chemical environments. More information on the manner in which spectra in this collection were collected can be found here.
Notice: Concentration information is not available for this spectrum and, therefore, molar absorptivity values cannot be derived.
Additional Data
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Owner | COBLENTZ SOC. Collection (C) 2018 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
---|---|
Source reference | COBLENTZ NO. 05139 |
Date | 1961/08/08 |
Name(s) | valine 2-AMINO-3-METHYL-BUTANOIC ACID |
State | SOLID (KBr DISC) |
Instrument | PERKIN-ELMER 21 (GRATING) |
Instrument parameters | FILTER AT ABOUT 10 MICRONS |
Path length | SPECTRAL FEATURE AT 1000 CM-1 IS AN ARTIFACT CAUSED BY FILTER CHANGE |
Resolution | 2 |
Sampling procedure | TRANSMISSION |
Data processing | DIGITIZED BY COBLENTZ SOCIETY (BATCH I) FROM HARD COPY |
Melting point | 315 C |
Mass spectrum (electron ionization)
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, 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: NIST Mass Spectrometry Data Center, William E. Wallace, director
Spectrum
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Additional Data
View image of digitized spectrum (can be printed in landscape orientation).
Due to licensing restrictions, this spectrum cannot be downloaded.
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 | H.FR.GRUTZMACHER HAMBURG UNIV., HAMBURG, GERMANY, F.R.G. |
NIST MS number | 26146 |
References
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, 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.
Vasil'ev, Borodin, et al., 1991
Vasil'ev, V.P.; Borodin, V.A.; Kopnyshev, S.B.,
Calculation of the standard enthalpies of combustion and of formation of crystalline organic acids and complexones from the energy contributions of atomic groups,
Russ. J. Phys. Chem. (Engl. Transl.), 1991, 65, 29-32. [all data]
Hutchens, Cole, et al., 1963
Hutchens, J.O.; Cole, A.G.; Stout, J.W.,
Heat capacities from 11 to 305°K., entropies, and free energies of formation of L-valine, L-isoleucine, and L-leucine,
J. Phys. Chem., 1963, 67, 1128-1130. [all data]
Tsuzuki and Hunt, 1957
Tsuzuki, T.; Hunt, H.,
Heats of combustion. VI. The heats of combustion of some amino acids,
J. Phys. Chem., 1957, 61, 1668. [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]
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]
Svec and Clyde, 1965, 2
Svec, H.J.; Clyde, D.D.,
Vapor Pressures of Some α-Amino Acids.,
J. Chem. Eng. Data, 1965, 10, 2, 151-152, https://doi.org/10.1021/je60025a024
. [all data]
Clyde and Svec, 1964
Clyde, D.D.; Svec, H.,
, U. S. Atomic Energy Comm. IS-790, 1964, 1. [all data]
Chiarelli and Gross, 1989
Chiarelli, M. Paul.; Gross, Michael L.,
Amino acid and tripeptide mixture analysis by laser desorption Fourier-transform mass spectrometry,
Anal. Chem., 1989, 61, 17, 1895-1900, https://doi.org/10.1021/ac00192a023
. [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]
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]
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]
Notes
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), 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 ΔsubH Enthalpy of sublimation - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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