Acetylacetone
- Formula: C5H8O2
- Molecular weight: 100.1158
- IUPAC Standard InChIKey: YRKCREAYFQTBPV-UHFFFAOYSA-N
- CAS Registry Number: 123-54-6
- 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. - Other names: 2,4-Pentanedione; Acetoacetone; Diacetylmethane; Pentane-2,4-dione; 2-Propanone, acetyl-; 2,4-Dioxopentane; 2,4-Pentadione; CH3COCH2COCH3; Acetone, acetyl-; ACAC; Pentanedione; Pentanedione-2,4; Acetyl 2-propanone; UN 2310; 2,4-Pentandione; Pentan-2,4-dione; NSC 5575
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Reaction thermochemistry data
Go To: Top, Gas phase ion energetics data, Gas Chromatography, 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:
B - John E. Bartmess
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
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
C5H7O2- + =
By formula: C5H7O2- + H+ = C5H8O2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1438. ± 8.8 | kJ/mol | G+TS | Taft and Bordwell, 1988 | gas phase; at 330K: neutral enol/keto ratio should be 8:1 ( Strohmeier and Höhne, 1952); B |
ΔrH° | 1438. ± 9.6 | kJ/mol | G+TS | Cumming and Kebarle, 1978 | gas phase; At 500K: neutral enol/keto ratio is 1.7:1, Folkendt, Weiss-Lopez, et al., 1989. ΔH=-4.7 kcal/mol, enol favored. Carbonyls anti in anion, via calc: Irikura, 1999; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1409. ± 8.4 | kJ/mol | IMRE | Taft and Bordwell, 1988 | gas phase; at 330K: neutral enol/keto ratio should be 8:1 ( Strohmeier and Höhne, 1952); B |
ΔrG° | 1408. ± 8.4 | kJ/mol | IMRE | Cumming and Kebarle, 1978 | gas phase; At 500K: neutral enol/keto ratio is 1.7:1, Folkendt, Weiss-Lopez, et al., 1989. ΔH=-4.7 kcal/mol, enol favored. Carbonyls anti in anion, via calc: Irikura, 1999; B |
By formula: C5H8O2 = C5H8O2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -7.9 ± 0.4 | kJ/mol | Kin | Schweig, Vermeer, et al., 1974 | liquid phase; Photoelectron spectroscopy; ALS |
ΔrH° | -10. ± 0.8 | kJ/mol | Eqk | Thompson and Allred, 1971 | liquid phase; solvent: Cyclohexane; NMR, UV; ALS |
ΔrH° | -12. ± 0.8 | kJ/mol | Eqk | Calmon, 1969 | liquid phase; ALS |
By formula: Cl- + C5H8O2 = (Cl- • C5H8O2)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrG° | 56.07 | kJ/mol | TDEq | French, Ikuta, et al., 1982 | gas phase; B |
Free energy of reaction
ΔrG° (kJ/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
46.0 | 421. | PHPMS | French, Ikuta, et al., 1982 | gas phase; M |
By formula: I- + C5H8O2 = (I- • C5H8O2)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 63.2 ± 4.2 | kJ/mol | TDAs | Caldwell, Masucci, et al., 1989 | gas phase; B,M |
By formula: C5H8O2 = C6H10O3
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -19.5 ± 0.75 | kJ/mol | Eqk | Folkendt, Weiss-Lopez, et al., 1985 | gas phase; NMR; ALS |
By formula: C5H8O2 = C5H8O2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 16.8 | kJ/mol | Eqk | Mines and Thompson, 1975 | gas phase; ALS |
Gas phase ion energetics data
Go To: Top, Reaction thermochemistry data, Gas Chromatography, 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
L - Sharon G. Lias
Data compiled as indicated in comments:
B - John E. Bartmess
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 |
---|---|---|---|---|---|
IE (evaluated) | 8.85 ± 0.02 | eV | N/A | N/A | L |
Quantity | Value | Units | Method | Reference | Comment |
Proton affinity (review) | 873.5 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 836.8 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
8.85 ± 0.05 | PE | Houk, Davis, et al., 1973 | LLK |
8.82 ± 0.02 | PI | Shigorin, Filyugina, et al., 1967 | RDSH |
8.87 ± 0.03 | PI | Watanabe, Nakayama, et al., 1962 | RDSH |
9.63 ± 0.01 | PE | Hush, Livett, et al., 1987 | Vertical value; LBLHLM |
9.15 | PE | Cauletti, Furlani, et al., 1980 | Vertical value; LLK |
9.00 | PE | Schweig, Vermeer, et al., 1974, 2 | Vertical value; LLK |
9.18 ± 0.07 | PE | Evans, Hamnett, et al., 1972 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C4H5O2+ | 10.7 ± 0.1 | CH3 | EI | Reichert and Westmore, 1969 | RDSH |
C4H5O2+ | 10.24 | CH3 | PI | Shigorin, Filyugina, et al., 1967 | RDSH |
De-protonation reactions
C5H7O2- + =
By formula: C5H7O2- + H+ = C5H8O2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1438. ± 8.8 | kJ/mol | G+TS | Taft and Bordwell, 1988 | gas phase; at 330K: neutral enol/keto ratio should be 8:1 ( Strohmeier and Höhne, 1952); B |
ΔrH° | 1438. ± 9.6 | kJ/mol | G+TS | Cumming and Kebarle, 1978 | gas phase; At 500K: neutral enol/keto ratio is 1.7:1, Folkendt, Weiss-Lopez, et al., 1989. ΔH=-4.7 kcal/mol, enol favored. Carbonyls anti in anion, via calc: Irikura, 1999; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1409. ± 8.4 | kJ/mol | IMRE | Taft and Bordwell, 1988 | gas phase; at 330K: neutral enol/keto ratio should be 8:1 ( Strohmeier and Höhne, 1952); B |
ΔrG° | 1408. ± 8.4 | kJ/mol | IMRE | Cumming and Kebarle, 1978 | gas phase; At 500K: neutral enol/keto ratio is 1.7:1, Folkendt, Weiss-Lopez, et al., 1989. ΔH=-4.7 kcal/mol, enol favored. Carbonyls anti in anion, via calc: Irikura, 1999; B |
Gas Chromatography
Go To: Top, Reaction thermochemistry data, 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: NIST Mass Spectrometry Data Center, William E. Wallace, director
Kovats' RI, non-polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Capillary | DB-5 | 130. | 786.6 | Mijin and Antonovic, 2004 | 60. m/0.321 mm/0.25 μm, N2 |
Capillary | DB-5 | 150. | 787.25 | Mijin and Antonovic, 2004 | 60. m/0.321 mm/0.25 μm, N2 |
Capillary | DB-5 | 170. | 763.43 | Mijin and Antonovic, 2004 | 60. m/0.321 mm/0.25 μm, N2 |
Capillary | DB-5 | 190. | 791. | Mijin and Antonovic, 2004 | 60. m/0.321 mm/0.25 μm, N2 |
Packed | SE-30 | 150. | 775. | Tiess, 1984 | Ar, Gas Chrom Q (80-100 mesh); Column length: 3. m |
Packed | Apiezon L | 120. | 754. | Bogoslovsky, Anvaer, et al., 1978 | Celite 545 |
Packed | Apiezon L | 160. | 771. | Bogoslovsky, Anvaer, et al., 1978 | Celite 545 |
Packed | SE-30 | 150. | 779. | Haken, Ho, et al., 1975 | Column length: 3.7 m |
Packed | Squalane | 180. | 771. | Vernon and Edwards, 1975 | N2, Celite; Column length: 1. m |
Van Den Dool and Kratz RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | HP-5MS | 783. | Pino, Mesa, et al., 2005 | 30. m/0.25 mm/0.25 μm, He, 60. C @ 2. min, 4. K/min, 250. C @ 20. min |
Capillary | BP-5 | 787. | Whitfield and Mottram, 1999 | He, 60. C @ 5. min, 4. K/min; Column length: 50. m; Column diameter: 0.32 mm; Tend: 250. C |
Capillary | DB-5 | 782. | Madruga and Mottram, 1998 | 30. m/0.32 mm/1. μm, 60. C @ 5. min, 4. K/min, 250. C @ 20. min |
Capillary | HP-1 | 795. | Kuo and Ho, 1992 | 50. m/0.32 mm/1.05 μm, He, 2. K/min; Tstart: 40. C; Tend: 260. C |
Capillary | DB-1 | 756. | Zhang and Ho, 1991 | 60. m/0.25 mm/0.25 μm, He, 2. K/min, 220. C @ 10. min; Tstart: 40. C |
Capillary | DB-1 | 760. | Zhang and Ho, 1991, 2 | 60. m/0.25 mm/0.25 μm, He, 2. K/min, 220. C @ 10. min; Tstart: 40. C |
Capillary | DB-1 | 753. | Flath, Light, et al., 1990 | 50. C @ 0.1 min, 4. K/min; Column length: 60. m; Column diameter: 0.32 mm; Tend: 250. C |
Van Den Dool and Kratz RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-5 | 799. | Parker, Hassell, et al., 2000 | 50. m/0.32 mm/0.5 μm, He; Program: oC(5min) => 60C/min => 60C (5min) => 4C/min => 250C |
Van Den Dool and Kratz RI, polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Supelcowax-10 | 1196. | Bianchi, Careri, et al., 2007 | 30. m/0.25 mm/0.25 μm, He; Program: 35C(8min) => 4C/min => 60C => 6C/min => 160C => 20C/min => 200C(1min) |
Normal alkane RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | VF-5 MS | 778. | Leffingwell and Alford, 2011 | 60. m/0.32 mm/0.25 μm, Helium, 2. K/min, 260. C @ 28. min; Tstart: 30. C |
Capillary | VF-5 MS | 782. | Leffingwell and Alford, 2011 | 60. m/0.32 mm/0.25 μm, Helium, 2. K/min, 260. C @ 28. min; Tstart: 30. C |
Capillary | HP-5 MS | 783. | Radulovic, Blagojevic, et al., 2010 | 30. m/0.25 mm/0.25 μm, Helium, 5. K/min, 290. C @ 10. min; Tstart: 70. C |
Capillary | SPB-1 | 760. | Frerot, Velluz, et al., 2008 | 30. m/0.25 mm/1.0 μm, Helium, 60. C @ 5. min, 5. K/min; Tend: 250. C |
Capillary | DB-5 | 786. | Pino, Marbot, et al., 2003 | 30. m/0.25 mm/0.25 μm, H2, 60. C @ 10. min, 4. K/min, 280. C @ 40. min |
Normal alkane RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Squalane | 779. | Chen, 2008 | Program: not specified |
Capillary | SPB-1 | 764. | Flanagan, Streete, et al., 1997 | 60. m/0.53 mm/5. μm, He; Program: 40C(6min) => 5C/min => 80C => 10C/min => 200C |
Capillary | SPB-1 | 764. | Strete, Ruprah, et al., 1992 | 60. m/0.53 mm/5.0 μm, Helium; Program: 40 0C (6 min) 5 0C/min -> 80 0C 10 0C/min -> 200 0C |
Capillary | SPB-1 | 790. | Strete, Ruprah, et al., 1992 | 60. m/0.53 mm/5.0 μm, Helium; Program: not specified |
Capillary | Polydimethyl siloxanes | 775. | Schutz and Wollrab A., 1988 | Program: not specified |
Capillary | OV-1 | 804. | Ramsey and Flanagan, 1982 | Program: not specified |
Normal alkane RI, polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | AT-Wax | 1167. | Kiss, Csoka, et al., 2011 | 60. m/0.25 mm/0.25 μm, Helium, 4. K/min; Tstart: 60. C; Tend: 280. C |
Capillary | Carbowax 20M | 1200. | Seifert and King, 1982 | He, 50. C @ 10. min, 1. K/min, 170. C @ 60. min; Column length: 150. m; Column diameter: 0.64 mm |
Normal alkane RI, polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Carbowax 20M | 1230. | Ramsey and Flanagan, 1982 | Program: not specified |
References
Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, Gas Chromatography, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Taft and Bordwell, 1988
Taft, R.W.; Bordwell, F.G.,
Structural and Solvent Effects Evaluated from Acidities Measured in Dimethyl Sulfoxide and in the Gas Phase,
Acc. Chem. Res., 1988, 21, 12, 463, https://doi.org/10.1021/ar00156a005
. [all data]
Strohmeier and Höhne, 1952
Strohmeier, W.; Höhne, I.,
Keto-Enol-Umwandlung des Acetylacteons in Gaszustand,
Z. Naturfor., 1952, 7B, 184. [all data]
Cumming and Kebarle, 1978
Cumming, J.B.; Kebarle, P.,
Summary of gas phase measurements involving acids AH. Entropy changes in proton transfer reactions involving negative ions. Bond dissociation energies D(A-H) and electron affinities EA(A),
Can. J. Chem., 1978, 56, 1. [all data]
Folkendt, Weiss-Lopez, et al., 1989
Folkendt, M.M.; Weiss-Lopez, B.E.; Chauvel, J.P., Jr.; True, N.S.,
Gas-Phase 1H NMR Studies of Keto-Enol Tautomerization of Acetylacetone, Methyl Acetoacetate, and Ethyl Acetoacetate,
J. Phys. Chem., 1989, 89, 15, 3347, https://doi.org/10.1021/j100261a038
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Irikura, 1999
Irikura, K.K.,
Acetylacetonate (acac) anion in the gas phase: predicted structures, vibrational spectra, and photodetachment energies,
Int. J. Mass Spectrom., 1999, 187, 577-587, https://doi.org/10.1016/S1387-3806(98)14192-1
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Schweig, Vermeer, et al., 1974
Schweig, A.; Vermeer, H.; Weidner, U.,
A photoelectron spectroscopic study of keto-enol tautomerism in acetylacetones - a new application of photoelectron spectroscopy,
Chem. Phys. Lett., 1974, 26, 229-233. [all data]
Thompson and Allred, 1971
Thompson, D.W.; Allred, A.L.,
Keto-enol equilibria in 2,4-Pentanedione and 3,3-dideuterio-2,4-pentanedione,
J. Phys. Chem., 1971, 75, 433-435. [all data]
Calmon, 1969
Calmon, J.P.,
Thermodynamic functions of enolization of aliphatic β-diketones,
C. R. Acad. Sci. Paris, 1969, 268, 1435-1438. [all data]
French, Ikuta, et al., 1982
French, M.A.; Ikuta, S.; Kebarle, P.,
Hydrogen bonding of O-H and C-H hydrogen donors to Cl-. Results from mass spectrometric measurement of the ion-molecule equilibria RH + Cl- = RHCl-,
Can. J. Chem., 1982, 60, 1907. [all data]
Caldwell, Masucci, et al., 1989
Caldwell, G.W.; Masucci, J.A.; Ikonomou, M.G.,
Negative Ion Chemical Ionization Mass Spectrometry - Binding of Molecules to Bromide and Iodide Anions,
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Folkendt, Weiss-Lopez, et al., 1985
Folkendt, M.M.; Weiss-Lopez, B.E.; Chauvel, J.P., Jr.; True, N.S.,
Gas-phase 1H NMR studies of keto-enol tautomerism of acetylacetone, methyl acetoacetate, and ethyl acetoacetate,
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Mines and Thompson, 1975
Mines, G.W.; Thompson, H.,
Infrared and photoelectron spectra, and keto-enol tautomerism of acetylacetones and acetoacetic esters,
Proc. Roy. Soc. London A, 1975, 342, 327-339. [all data]
Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G.,
Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update,
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Houk, Davis, et al., 1973
Houk, K.N.; Davis, L.P.; Newkome, G.R.; Duke, R.E., Jr.; Nauman, R.V.,
Photoelectron spectroscopy of cyclic β-diketones their enolone tautomers,
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Shigorin, Filyugina, et al., 1967
Shigorin, D.N.; Filyugina, A.D.; Potapov, V.K.,
Role of intramolecular hydrogen bonding in the ionisation and dissociation of compounds,
Zh. Fiz. Khim., 1967, 41, 2336, In original 1255. [all data]
Watanabe, Nakayama, et al., 1962
Watanabe, K.; Nakayama, T.; Mottl, J.,
Ionization potentials of some molecules,
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Hush, Livett, et al., 1987
Hush, N.S.; Livett, M.K.; Peel, J.B.; Willett, G.D.,
Variable-temperature ultraviolet photoelectron spectroscopy of the keto-enol tautomers of pentane-2,4-dione,
Aust. J. Chem., 1987, 40, 599. [all data]
Cauletti, Furlani, et al., 1980
Cauletti, C.; Furlani, C.; Storto, G.,
Coordinative bond d-shell ionisations in the UV photoelectron spectra of bis({beta}-diketonato) cobalt (II) copper (II) complexes, their thio analogues,
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Schweig, Vermeer, et al., 1974, 2
Schweig, A.; Vermeer, H.; Weidner, U.,
A photoelectron spectroscopic study of keto-enol tautomerism in acetylacetones - a new application of photoelectron spectroscopy,
Chem. Phys. Lett., 1974, 26, 229. [all data]
Evans, Hamnett, et al., 1972
Evans, S.; Hamnett, A.; Orchard, A.F.; Lloyd, D.R.,
Study of the metal-oxygen bond in simple tris-chelate complexes by He(I) photoelectron spectroscopy,
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Reichert and Westmore, 1969
Reichert, C.; Westmore, J.B.,
Mass spectral studies of metal chelates. IV.Mass spectra, appearance potentials, and coordinate bond energies of bis(acetylacetonate)metal(II) complexes of the first transition series,
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Mijin and Antonovic, 2004
Mijin, D.Z.; Antonovic, D.G.,
Temperature dependence of the Kovats retention indices for alkyl 1,3-diketones on a DB-5 capillary column,
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Tiess, 1984
Tiess, D.,
Gaschromatographische Retentionsindices von 125 leicht- bis mittelflüchtigen organischen Substanzen toxikologisch-analytischer Relevanz auf SE-30,
Wiss. Z. Wilhelm-Pieck-Univ. Rostock Math. Naturwiss. Reihe, 1984, 33, 6-9. [all data]
Bogoslovsky, Anvaer, et al., 1978
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Chromatographic constants in gas chromatography (in Russian), Standards Publ. House, Moscow, 1978, 192. [all data]
Haken, Ho, et al., 1975
Haken, J.K.; Ho, D.K.M.; Vaughan, C.E.,
Gas chromatography of homologous esters. VII. The retention behaviour of pyruvate esters and related carbonyl and carboxyl compounds,
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Vernon and Edwards, 1975
Vernon, F.; Edwards, G.T.,
Gas-liquid chromatography on fluorinated stationary phases. II. Fluorinated compounds containing a functional group,
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Pino, Mesa, et al., 2005
Pino, J.A.; Mesa, J.; Muñoz, Y.; Martí, M.P.; Marbot, R.,
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Whitfield and Mottram, 1999
Whitfield, F.B.; Mottram, D.S.,
Investigation of the reaction between 4-hydroxy-5-methyl-3(2H)-furanone and cysteine or hydrogen sulfide at pH 4.5,
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Madruga and Mottram, 1998
Madruga, M.S.; Mottram, D.S.,
The effect of pH on the formation of volatile compounds produced by heating a model system containing 5'-imp and cysteine,
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Kuo and Ho, 1992
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Volatile constituents of the solvent extracts of Welsh onions (Allium fistulosum L. variety Maichuon) and scallions (A. fistulosum L. variety caepitosum),
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Zhang and Ho, 1991
Zhang, Y.; Ho, C.-T.,
Formation of meatlike aroma compounds from thermal reaction of inosine 5'-monophosphate with cysteine and glutathione,
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Comparison of the volatile compounds formed from the thermal reaction of glucose with cysteine and glutathione,
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Flath, Light, et al., 1990
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Headspace Examination of Volatile Emissions from Ripening Papaya (Carica papaya L., Solo Variety),
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Parker, Hassell, et al., 2000
Parker, J.K.; Hassell, G.M.E.; Mottram, D.S.; Guy, R.C.E.,
Sensory and instrumental analyses of volatiles generated during the extrusion cooking of oat flours,
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Retention indices in the analysis of food aroma volatile compounds in temperature-programmed gas chromatography: Database creation and evaluation of precision and robustness,
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Leffingwell and Alford, 2011
Leffingwell, J.; Alford, E.D.,
Volatile constituents of the giant pufball mushroom (Calvatia gigantea),
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Radulovic, Blagojevic, et al., 2010
Radulovic, N.; Blagojevic, P.; Palic, R.,
Comparative study of the leaf volatiles of Arctostaphylos uva-ursi (L.) Spreng. and Vaccinium vitis-idaea L. (Ericaceae),
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Notes
Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, Gas Chromatography, References
- Symbols used in this document:
AE Appearance energy IE (evaluated) Recommended ionization energy T Temperature 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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