Glycine
- Formula: C2H5NO2
- Molecular weight: 75.0666
- IUPAC Standard InChIKey: DHMQDGOQFOQNFH-UHFFFAOYSA-N
- CAS Registry Number: 56-40-6
- Chemical structure:
This structure is also available as a 2d Mol file - Species with the same structure:
- Other names: Acetic acid, amino-; Aciport; Aminoacetic acid; Aminoethanoic acid; Glicoamin; Glycocoll; Glycolixir; Glycosthene; Padil; NH2CH2COOH; Amitone; Glycine, non-medical; Hampshire glycine; Athenon; Gly; Glycine, free base; Gyn-hydralin; 2-Aminoacetic acid; NSC 25936; Corilin (Salt/Mix)
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible 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: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | -390.5 ± 4.6 | kJ/mol | Ccr | Ngauv, Sabbah, et al., 1977 |
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 | -527.5 ± 0.5 | kJ/mol | Ccb | Vasil'ev, Borodin, et al., 1991 | ALS |
ΔfH°solid | -528.61 | kJ/mol | Ccr | Ngauv, Sabbah, et al., 1977 | ALS |
ΔfH°solid | -537.2 | kJ/mol | Ccb | Hutchens, Cole, et al., 1963 | ALS |
ΔfH°solid | -528.52 ± 0.42 | kJ/mol | Ccb | Huffman, Fox, et al., 1937 | Author's hf298=-126.69 kcal/mol; ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°solid | -975. ± 8. | kJ/mol | AVG | N/A | Average of 8 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
S°solid,1 bar | 103.51 | J/mol*K | N/A | Hutchens, Cole, et al., 1960 | DH |
S°solid,1 bar | 109.2 | J/mol*K | N/A | Parks, Huffman, et al., 1933 | Extrapolation below 90 K, 31.59 J/mol*K.; DH |
Constant pressure heat capacity of solid
Cp,solid (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
95. | 298. | Badelin, Kulikov, et al., 1990 | T = 298, 313, 333, 348 K.; DH |
95.1 | 298. | Kulikov, Kozlov, et al., 1989 | T = 298 to 348 K.; DH |
99.3 | 298.15 | Spink and Wads, 1975 | DH |
99.20 | 298.15 | Hutchens, Cole, et al., 1960 | T = 11 to 305 K.; DH |
100.50 | 299.5 | Parks, Huffman, et al., 1933 | T = 93 to 300 K. Value is unsmoothed experimental datum.; 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
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔsubH° | 138.1 ± 4.6 | kJ/mol | C | Ngauv, Sabbah, et al., 1977 | ALS |
ΔsubH° | 138.1 ± 4.6 | kJ/mol | C | Nguon Ngauv, Sabbah, et al., 1977 | Based on data from 413. to 450. K.; AC |
Enthalpy of sublimation
ΔsubH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
137. ± 2. | 419. | TE,ME | de Kruif, Voogd, et al., 1979 | Based on data from 408. to 431. K.; AC |
136. ± 0.4 | 455. | V | Svec and Clyde, 1965 | ALS |
136.4 ± 4.0 | 462. | ME | Svec and Clyde, 1965, 2 | Based on data from 453. to 471. K. See also Cox and Pilcher, 1970, Clyde and Svec, 1964, and Chiarelli and Gross, 1989.; AC |
131. ± 2. | 414. | ME | Takagi, Chihara, et al., 1959 | Based on data from 412. to 417. K.; AC |
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)
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
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 |
---|---|---|---|---|---|
Proton affinity (review) | 886.5 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 852.2 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Proton affinity at 298K
Proton affinity (kJ/mol) | Reference | Comment |
---|---|---|
886.3 ± 3.1 | Bouchoux, Buisson, et al., 2004 | MM |
883.1 ± 1.9 | Bouchoux and Salpin, 2003 | T = 298K; MM |
Gas basicity at 298K
Gas basicity (review) (kJ/mol) | Reference | Comment |
---|---|---|
855.4 ± 3.6 | Bouchoux, Buisson, et al., 2004 | MM |
851.1 ± 1.9 | Bouchoux and Salpin, 2003 | T = 298K; MM |
856. ± 3. | Wu and Lebrilla, 1995 | T = 300K; MM |
Protonation entropy at 298K
Protonation entropy (J/mol*K) | Reference | Comment |
---|---|---|
2. ± 6. | Bouchoux, Buisson, et al., 2004 | MM |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
8.9 | PE | Cannington and Ham, 1983 | LBLHLM |
8.8 | PE | Debies and Rabalais, 1974 | LLK |
9.21 ± 0.05 | EI | Zaretskii, Sadovskaya, et al., 1971 | LLK |
9.25 ± 0.10 | EI | Svec and Junk, 1967 | RDSH |
9.30 | CTS | Slifkin and Allison, 1967 | RDSH |
10.0 | PE | Cannington and Ham, 1983 | Vertical value; LBLHLM |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
CH4N+ | 10.27 ± 0.05 | ? | EI | Zaretskii, Sadovskaya, et al., 1971 | LLK |
CH4N+ | 10.23 ± 0.09 | ? | EI | Svec and Junk, 1967 | RDSH |
CH4N+ | 10.1 ± 0.2 | ? | EI | Junk and Svec, 1963 | RDSH |
De-protonation reactions
C2H4NO2- + =
By formula: C2H4NO2- + H+ = C2H5NO2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1434. ± 9.2 | kJ/mol | CIDC | Jones, Bernier, et al., 2007 | gas phase; B |
ΔrH° | 1429. ± 8.8 | kJ/mol | G+TS | Caldwell, Renneboog, et al., 1989 | gas phase; B |
ΔrH° | 1433. ± 8.8 | kJ/mol | G+TS | Locke and McIver, 1983 | gas phase; B |
ΔrH° | 1410. ± 5.9 | kJ/mol | EIAE | Muftakhov, Vasil'ev, et al., 1999 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1400. ± 8.4 | kJ/mol | IMRE | Caldwell, Renneboog, et al., 1989 | gas phase; B |
ΔrG° | 1404. ± 8.4 | kJ/mol | IMRE | Locke and McIver, 1983 | gas phase; B |
IR Spectrum
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), UV/Visible spectrum, References, Notes
Data compiled by: Coblentz Society, Inc.
- Not specified, most likely a prism, grating, or hybrid spectrometer.; (NO SPECTRUM, ONLY SCANNED IMAGE IS AVAILABLE)
- SOLID (MULL, KBr DISC) $$INACTIVE KBr PLATES AROUND 300-200 CM-1; PERKIN-ELMER 521 (GRATING); DIGITIZED BY COBLENTZ SOCIETY (BATCH I) FROM HARD COPY; 2 cm-1 resolution
Mass spectrum (electron ionization)
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, UV/Visible 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
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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 | Japan AIST/NIMC Database- Spectrum MS-NW- 601 |
NIST MS number | 229287 |
UV/Visible spectrum
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), References, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Spectrum
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Additional Data
View image of digitized spectrum (can be printed in landscape orientation).
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Download spectrum in JCAMP-DX format.
Source | Pestemer and Alslev-Klinker, 1949 |
---|---|
Owner | INEP CP RAS, NIST OSRD Collection (C) 2007 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
Origin | INSTITUTE OF ENERGY PROBLEMS OF CHEMICAL PHYSICS, RAS |
Source reference | RAS UV No. 11966 |
Instrument | Quartz spectrograph |
Melting point | 262 dec |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, 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]
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]
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]
Hutchens, Cole, et al., 1960
Hutchens, J.O.; Cole, A.G.; Stout, J.W.,
Heat capacities from 11 to 305K. and entropies of L-alanine and glycine,
J. Am. Chem. Soc., 1960, 82, 4813-4815. [all data]
Parks, Huffman, et al., 1933
Parks, G.S.; Huffman, H.M.; Barmore, M.,
Thermal data on organic compounds. XI. The heat capacities,
entropies and free energies of ten compounds containing oxygen or nitrogen. J. Am. Chem. Soc., 1933, 55, 2733-2740. [all data]
Badelin, Kulikov, et al., 1990
Badelin, V.G.; Kulikov, O.V.; Batagin, V.S.; Udzig, E.; Zielenkiewicz, A.; Zielenkiewicz, W.; Krestov, G.A.,
Physico-chemical properties of peptides and their solutions,
Thermochim. Acta, 1990, 169, 81-93. [all data]
Kulikov, Kozlov, et al., 1989
Kulikov, O.V.; Kozlov, V.A.; Malenkina, L.I.; Badelin, V.G.,
Heat capacities of amino acids and peptides and excess characteristics ot their aqueous solutions, Sbornik Nauch. Trud., Termodin. Rast. neelect., Ivanovo,
Inst. nevod. rast., 1989, Akad. [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]
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]
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]
Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G.,
Thermochemistry of Organic and Organometallic Compounds, Academic Press Inc., London, 1970, 643. [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]
Takagi, Chihara, et al., 1959
Takagi, Sadao; Chihara, Hideaki; Seki, Syûzô,
Vapor Pressure of Molecular Crystals. XIII. Vapor Pressure of α-Glycine Crystal. The Energy of Proton Transfer,
Bull. Chem. Soc. Jpn., 1959, 32, 1, 84-88, https://doi.org/10.1246/bcsj.32.84
. [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, Buisson, et al., 2004
Bouchoux, G.; Buisson, D.A.; Colas, C.; Sablier, M.,
Protonation thermochemistry of alpha-amino acids bearing a basic residue,
European J. Mass Spectrom., 2004, 10, 977. [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]
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]
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]
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]
Zaretskii, Sadovskaya, et al., 1971
Zaretskii, V.I.; Sadovskaya, V.L.; Wulfson, N.S.; Sizoy, V.F.; Merimson, V.G.,
Mass spectrometry of steroid systems-XXI. Appearance and ionization potentials for the stereoisomers of the D-homoestrane series,
Org. Mass Spectrom., 1971, 5, 1179. [all data]
Svec and Junk, 1967
Svec, H.J.; Junk, G.A.,
Electron-impact studies of substituted alkanes,
J. Am. Chem. Soc., 1967, 89, 790. [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]
Junk and Svec, 1963
Junk, G.; Svec, H.,
The mass spectra of the α-amino acids,
J. Am. Chem. Soc., 1963, 85, 839. [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]
Caldwell, Renneboog, et al., 1989
Caldwell, G.; Renneboog, R.; Kebarle, P.,
Gas Phase Acidities of Aliphatic Carboxylic Acids, Based on Measurements of Proton Transfer Equilibria,
Can. J. Chem., 1989, 67, 4, 661, https://doi.org/10.1139/v89-092
. [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]
Muftakhov, Vasil'ev, et al., 1999
Muftakhov, M.V.; Vasil'ev, Y.V.; Mazunov, V.A.,
Determination of electron affinity of carbonyl radicals by means of negative ion mass spectrometry,
Rapid Commun. Mass Spectrom., 1999, 13, 12, 1104-1108, https://doi.org/10.1002/(SICI)1097-0231(19990630)13:12<1104::AID-RCM619>3.0.CO;2-C
. [all data]
Pestemer and Alslev-Klinker, 1949
Pestemer, M.; Alslev-Klinker, A.,
Z. Elektrochem, 1949, 53, 387. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, References
- Symbols used in this document:
AE Appearance energy 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°gas Enthalpy of formation of gas 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 ΔsubH° Enthalpy of sublimation at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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