3-Penten-2-one, 4-methyl-

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Gas 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity Value Units Method Reference Comment
Δfgas-178.28 ± 0.64kJ/molCcbSteele, Chirico, et al., 1997 
Δfgas-184.5 ± 2.5kJ/molEqkGuthrie, 1978 

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
L - Sharon G. Lias

Data compiled as indicated in comments:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard

View reactions leading to C6H10O+ (ion structure unspecified)

Quantity Value Units Method Reference Comment
IE (evaluated)9.10 ± 0.02eVN/AN/AL
Quantity Value Units Method Reference Comment
Proton affinity (review)878.7kJ/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity846.9kJ/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
9.11PEMasclet and Mouvier, 1978LLK
9.08 ± 0.03PIWatanabe, Nakayama, et al., 1962RDSH
8.89 ± 0.05EIOmura, Higasi, et al., 1956RDSH

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C5H7O+9.48CH3EIAlai, Attardo, et al., 1985LBLHLM

Gas Chromatography

Go To: Top, Gas phase 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

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Column type Active phase Temperature (C) I Reference Comment
PackedApiezon L120.771.Bogoslovsky, Anvaer, et al., 1978Celite 545

Kovats' RI, non-polar column, temperature ramp

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Column type Active phase I Reference Comment
CapillaryOV-101782.Yamaguchi and Shibamoto, 1981N2, 2. K/min; Column length: 70. m; Column diameter: 0.28 mm; Tstart: 80. C; Tend: 200. C

Kovats' RI, polar column, temperature ramp

View large format table.

Column type Active phase I Reference Comment
CapillaryCarbowax 20M1118.Tressl, Friese, et al., 1978He, 2. K/min; Column length: 50. m; Column diameter: 0.28 mm; Tstart: 70. C; Tend: 190. C

Van Den Dool and Kratz RI, non-polar column, temperature ramp

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Column type Active phase I Reference Comment
CapillaryHP-1778.Zhang, Dorjpalam, et al., 199250. m/0.32 mm/1.5 μm, 2. K/min, 220. C @ 30. min; Tstart: 40. C

Van Den Dool and Kratz RI, polar column, temperature ramp

View large format table.

Column type Active phase I Reference Comment
CapillaryZB-Wax1118.Ledauphin, Saint-Clair, et al., 200430. m/0.25 mm/0.15 μm, He, 35. C @ 5. min, 5. K/min, 220. C @ 10. min
CapillaryFFAP1159.Stephan and Steinhart, 199960. m/0.25 mm/0.5 μm, 50. C @ 3. min, 5. K/min, 230. C @ 15. min
CapillaryDB-Wax1131.Shimoda, Shigematsu, et al., 199560. m/0.25 mm/0.25 μm, 2. K/min; Tstart: 50. C; Tend: 230. C
CapillaryCP-WAX 57CB1136.Salter L.J., Mottram D.S., et al., 198860. C @ 5. min, 4. K/min; Column length: 50. m; Column diameter: 0.32 mm; Tend: 200. C

Van Den Dool and Kratz RI, polar column, custom temperature program

View large format table.

Column type Active phase I Reference Comment
CapillaryDB-Wax1125.Cantergiani, Brevard, et al., 200130. m/0.25 mm/0.25 μm; Program: 20C(30s) => fast => 60C => 4C/min => 220C (20min)

Normal alkane RI, non-polar column, isothermal

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Column type Active phase Temperature (C) I Reference Comment
PackedDC-400150.792.Anderson, 1968Helium, Gas-Pak (60-80 mesh); Column length: 3.0 m

Normal alkane RI, non-polar column, temperature ramp

View large format table.

Column type Active phase I Reference Comment
CapillaryHP-5 MS798.Lazarevic, Radulovic, et al., 201030. m/0.25 mm/0.25 μm, Helium, 5. K/min; Tstart: 70. C; Tend: 290. C
CapillaryHP-5801.1Leffingwell and Alford, 200560. m/0.32 mm/0.25 μm, He, 30. C @ 2. min, 2. K/min, 260. C @ 28. min
CapillaryHP-5778.N/A30. m/0.32 mm/0.25 μm, Helium, 40. C @ 2. min, 5. K/min, 250. C @ 5. min
CapillaryDB-5792.Tellez, Khan, et al., 200230. m/0.25 mm/0.25 μm, He, 3. K/min; Tstart: 60. C; Tend: 240. C
CapillaryDB-5800.Tellez, Canel, et al., 199930. m/0.25 mm/0.25 μm, He, 3. K/min; Tstart: 60. C; Tend: 240. C
CapillaryDB-1780.Tai and Ho, 199860. m/0.32 mm/1.0 μm, He, 2. K/min; Tstart: 40. C; Tend: 280. C
CapillaryOV-101787.Zenkevich and Kulikova, 1993He, 3. K/min; Column length: 54. m; Column diameter: 0.26 mm; Tstart: 50. C; Tend: 230. C

Normal alkane RI, non-polar column, custom temperature program

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Column type Active phase I Reference Comment
CapillaryHP-5798.Zhao, Li, et al., 200830. m/0.25 mm/0.25 μm; Program: 40 0C (2 min) 5 0C/min -> 80 0C 7 oC/min -> 160 0C 9 0C/min -> 200 0C 20 0C/min -> 280 0C (10 min)
CapillaryHP-5804.Zhao, Li, et al., 200830. m/0.25 mm/0.25 μm; Program: not specified
CapillaryDB-5 MS782.Zhu, Li, et al., 200830. m/0.25 mm/0.25 μm, Helium; Program: 50 0C (2.8 min) 5.5 0C/min -> 140 0C (1 min) 4.5 oC/min -> 220 0C -> 225 0C (2 min) 3.4 0C/min -> 265 0C (5 min)
CapillaryDB-5 MS797.Zhu, Li, et al., 200830. m/0.25 mm/0.25 μm, Helium; Program: 50 0C (2.8 min) 5.5 0C/min -> 140 0C (1 min) 4.5 oC/min -> 220 0C -> 225 0C (2 min) 3.4 0C/min -> 265 0C (5 min)
CapillaryRTX-5798.Ádámová, Orinák, et al., 200530. m/0.25 mm/0.25 μm, N2; Program: not specified
CapillaryRTX-5798.Ádámová, Orinák, et al., 200530. m/0.25 mm/0.25 μm, N2; Program: not specified
CapillaryRTX-5 MS802.Machiels and Istasse, 200360. m/0.25 mm/0.5 μm, He; Program: 35C (3min) => 10C/min => 50C => 4C/min => 200C => 50C/min => 250C (10min)
CapillaryBPX-5798.Machiels, van Ruth, et al., 200360. m/0.32 mm/1. μm, He; Program: 40C (4min) => 2C/min => 90C => 4C/min => 130C => 8C/min => 250 C (10min)
CapillaryBPX-5798.Machiels, van Ruth, et al., 200360. m/0.32 mm/1. μm, He; Program: 40C (4min) => 2C/min => 90C => 4C/min => 130C => 8C/min => 250 C (10min)
CapillaryMethyl Silicone783.Zenkevich, 1999Program: not specified
CapillaryHP-5804.Timón, Ventanas, et al., 199850. m/0.32 mm/0.52 μm, He; Program: 35 0C 10 0C/min -> 200 0C (20 min) 5 0C/min -> 230 0C (50 min)
CapillaryPolydimethyl siloxanes783.Zenkevich, 1997Program: not specified

Normal alkane RI, polar column, temperature ramp

View large format table.

Column type Active phase I Reference Comment
CapillaryZB-Wax1114.N/A30. m/0.32 mm/0.25 μm, Helium, 40. C @ 2. min, 5. K/min, 250. C @ 5. min
CapillaryRTX-Wax1152.Galindo-Cuspinera, Lubran, et al., 200260. m/0.25 mm/0.5 μm, He, 40. C @ 5. min, 5. K/min, 180. C @ 20. min
CapillaryDB-Wax1129.Werkhoff, Güntert, et al., 199860. m/0.32 mm/0.25 μm, H2, 3. K/min; Tstart: 60. C; Tend: 220. C
CapillaryDB-Wax1113.Pollak and Berger, 199630. m/0.32 mm/0.5 μm, He, 40. C @ 1. min, 3. K/min, 210. C @ 25. min
CapillaryCarbowax 20M1110.Kawakami, Ganguly, et al., 199560. C @ 4. min, 2. K/min; Column length: 60. m; Column diameter: 0.25 mm; Tend: 180. C
CapillaryCarbowax 20M1110.Kawakami and Kobayashi, 1991He, 60. C @ 4. min, 2. K/min; Column length: 50. m; Column diameter: 0.25 mm; Tend: 180. C
CapillaryDB-Wax1127.Takeoka, Flath, et al., 198860. m/0.25 mm/0.25 μm, H2, 30. C @ 2. min, 2. K/min; Tend: 180. C
CapillaryDB-Wax1127.Takeoka, Flath, et al., 198860. m/0.25 mm/0.25 μm, H2, 30. C @ 2. min, 2. K/min; Tend: 180. C

Normal alkane RI, polar column, custom temperature program

View large format table.

Column type Active phase I Reference Comment
CapillarySOLGel-Wax1140.Johanningsmeier and McFeeters, 201130. m/0.25 mm/0.25 μm, Helium; Program: 40 0C (2 min) 5 0C/min -> 140 0C 10 0C/min -> 250 0C (3 min)
CapillarySOLGel-Wax1131.Johanningsmeier and McFeeters, 201130. m/0.25 mm/0.25 μm, Helium; Program: not specified
CapillaryCP-Wax 52 CB1111.Kaack and Christensen, 200850. m/0.25 mm/0.29 μm, Helium; Program: 33 0C (1 min) 2 0C/min -> 130 0C 10 0C/min -> 220 0C
CapillaryHP-Innowax1127.Narain, Galvao, et al., 200730. m/0.25 mm/0.25 μm, He; Program: 30C(5min) => 7C/min => 100C(5min) => 1C/min => 130C => 10C/min => 195C(45min)
CapillaryHP-Innowax1128.Narain, Galvao, et al., 200730. m/0.25 mm/0.25 μm, He; Program: 30C(5min) => 7C/min => 100C(5min) => 1C/min => 130C => 10C/min => 195C(45min)
CapillarySupelcowax 101125.Castioni and Kapetanidis, 199660. m/0.25 mm/0.25 μm, Helium; Program: 60 0C (10 min) 2 0C/min -> 80 0C 3 0C/min -> 100 0C 4 0C/min -> 220 0C (30 min)
CapillarySupelcowax 101137.Castioni and Kapetanidis, 199660. m/0.25 mm/0.25 μm, Helium; Program: not specified

References

Go To: Top, Gas phase 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.

Steele, Chirico, et al., 1997
Steele, W.V.; Chirico, R.D.; Cowell, A.B.; Knipmeyer, S.E.; Nguyen, A., Thermodynamic properties and ideal-gas enthalpies of formation for 2-aminoisobutyric acid (2-methylalanine), acetic acid, (4-methyl-3-penten-2-one), 4-methylpent-1-ene, 2,2'-bis(phenylthio)propane, and glycidyl phenyl ether (1,2-epoxy-3-phenoxypropane), J. Chem. Eng. Data, 1997, 42, 1052-1066. [all data]

Guthrie, 1978
Guthrie, J.P., Equilibrium constants for a series of simple aldol condensations, and linear free energy relations with other carbonyl addition reactions, Can. J. Chem., 1978, 56, 962-973. [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]

Masclet and Mouvier, 1978
Masclet, P.; Mouvier, G., Etude par spectrometrie photoelectronique d'aldehydes et de cetones ethyleniques conjugues, J. Electron Spectrosc. Relat. Phenom., 1978, 14, 77. [all data]

Watanabe, Nakayama, et al., 1962
Watanabe, K.; Nakayama, T.; Mottl, J., Ionization potentials of some molecules, J. Quant. Spectry. Radiative Transfer, 1962, 2, 369. [all data]

Omura, Higasi, et al., 1956
Omura, I.; Higasi, K.; Baba, H., Ionization potentials of some organic molecules. II. Aliphatic compounds, Bull. Chem. Soc. Japan, 1956, 29, 504. [all data]

Alai, Attardo, et al., 1985
Alai, M.; Attardo, G.G.; Rye, R.T.B., Formation threshold structures of some [C5H7O]+ ions: Use of general schemes for estimation of heats of formation of gas phase ions, Can. J. Chem., 1985, 63, 833. [all data]

Bogoslovsky, Anvaer, et al., 1978
Bogoslovsky, Yu.N.; Anvaer, B.I.; Vigdergauz, M.S., Chromatographic constants in gas chromatography (in Russian), Standards Publ. House, Moscow, 1978, 192. [all data]

Yamaguchi and Shibamoto, 1981
Yamaguchi, K.; Shibamoto, T., Volatile constituents of green tea, Gyokuro (Camellia sinensis L. var Yabukita), J. Agric. Food Chem., 1981, 29, 2, 366-370, https://doi.org/10.1021/jf00104a035 . [all data]

Tressl, Friese, et al., 1978
Tressl, R.; Friese, L.; Fendesack, F.; Köppler, H., Studies of the volatile composition of hops during storage, J. Agric. Food Chem., 1978, 26, 6, 1426-1430, https://doi.org/10.1021/jf60220a036 . [all data]

Zhang, Dorjpalam, et al., 1992
Zhang, Y.; Dorjpalam, B.; Ho, C.-T., Contribution of peptides to volatile formation in the Maillard reaction of casein hydrolysate with glucose, J. Agric. Food Chem., 1992, 40, 12, 2467-2471, https://doi.org/10.1021/jf00024a026 . [all data]

Ledauphin, Saint-Clair, et al., 2004
Ledauphin, J.; Saint-Clair, J.-F.; Lablanquie, O.; Guichard, H.; Founier, N.; Guichard, E.; Barillier, D., Identification of trace volatile compounds in freshly distilled calvados and cognac using preparative separations coupled with gas chromatography-mass spectrometry, J. Agric. Food Chem., 2004, 52, 16, 5124-5134, https://doi.org/10.1021/jf040052y . [all data]

Stephan and Steinhart, 1999
Stephan, A.; Steinhart, H., Identification of character impact odorants of different soybean lecithins, J. Agric. Food Chem., 1999, 47, 7, 2854-2859, https://doi.org/10.1021/jf981387g . [all data]

Shimoda, Shigematsu, et al., 1995
Shimoda, M.; Shigematsu, H.; Shiratsuchi, H.; Osajima, Y., Comparison of the odor concentrates by SDE and adsorptive column method from green tea infusion, J. Agric. Food Chem., 1995, 43, 6, 1616-1620, https://doi.org/10.1021/jf00054a037 . [all data]

Salter L.J., Mottram D.S., et al., 1988
Salter L.J.; Mottram D.S.; Whitfield, Volatile compounds produces in Maillard reactions involving glycine, ribose and phospholid, J. Sci. Food Agric., 1988, 46, 2, 227-242, https://doi.org/10.1002/jsfa.2740460211 . [all data]

Cantergiani, Brevard, et al., 2001
Cantergiani, E.; Brevard, H.; Krebs, Y.; Feria-Morales, A.; Amadò, R.; Yeretzian, C., Characterisation of the aroma of green Mexican coffee and identification of mouldy/earthy defect, Eur. Food Res. Technol., 2001, 212, 6, 648-657, https://doi.org/10.1007/s002170100305 . [all data]

Anderson, 1968
Anderson, D.G., USe of Kovats retention indices and response factors for the qualitative and quantitative analysis of coating solvents, J. Paint Technol., 1968, 40, 527, 549-557. [all data]

Lazarevic, Radulovic, et al., 2010
Lazarevic, J.; Radulovic, N.; Palic, R.; Zlatkovic, B., Chemical Analusis of volatile constituents of Berula erecta (Hudson) Coville subsp. erecta (Apiaceae) from Serbia, J. Essential Oil. Res., 2010, 22, 3, 153-156, https://doi.org/10.1080/10412905.2010.9700290 . [all data]

Leffingwell and Alford, 2005
Leffingwell, J.C.; Alford, E.D., Volatile constituents of Perique tobacco, Electron. J. Environ. Agric. Food Chem., 2005, 4, 2, 899-915. [all data]

Tellez, Khan, et al., 2002
Tellez, M.R.; Khan, I.A.; Kobaisy, M.; Schrader, K.K.; Dayan, F.E.; Osbrink, W., Composition of the essential oil of Lepidium meyenii (Walp.), Phytochemistry, 2002, 61, 2, 149-155, https://doi.org/10.1016/S0031-9422(02)00208-X . [all data]

Tellez, Canel, et al., 1999
Tellez, M.R.; Canel, C.; Rimando, A.M.; Duke, S.O., Differential accumulation of isoprenoids in glanded and glandless Artemisia annua L, Phytochemistry, 1999, 52, 6, 1035-1040, https://doi.org/10.1016/S0031-9422(99)00308-8 . [all data]

Tai and Ho, 1998
Tai, C.-Y.; Ho, C.-T., Influence of glutathione oxidation and pH on thermal formation of Maillard-type volatile compounds, J. Agric. Food Chem., 1998, 46, 6, 2260-2265, https://doi.org/10.1021/jf971111t . [all data]

Zenkevich and Kulikova, 1993
Zenkevich, I.G.; Kulikova, S.N., GC-MS Analysis of Products of Reactions of Unsaturated Compounds with Dimethyl Disulfide for Determination of Position of Double Bonds C=C, Vestnik St. Petersburg University. Ser. phys-khim., 1993, 2, 59-69. [all data]

Zhao, Li, et al., 2008
Zhao, Y.; Li, J.; Xu, Y.; Duan, H.; Fan, W.; Zhao, G., EXtraction, preparation and identification of volatile compounds in Changyu XO brandy, Chinese J. Chromatogr., 2008, 26, 2, 212-222, https://doi.org/10.1016/S1872-2059(08)60014-0 . [all data]

Zhu, Li, et al., 2008
Zhu, M.; Li, E.; He, H., Determination of volatile chemical constitutes in tea by simultaneous distillation extraction, vacuum hydrodistillation and thermal desrption, Chromatographia, 2008, 68, 7/8, 603-610, https://doi.org/10.1365/s10337-008-0732-1 . [all data]

Ádámová, Orinák, et al., 2005
Ádámová, M.; Orinák, A.; Halás, L., Retention indices as identification tool in pyrolysis-capillary gas chromatography, J. Chromatogr. A, 2005, 1087, 1-2, 131-141, https://doi.org/10.1016/j.chroma.2005.01.003 . [all data]

Machiels and Istasse, 2003
Machiels, D.; Istasse, L., Evaluation of two commercial solid-phase microextraction fibres for the analysis of target aroma compounds in cooked beef meat, Talanta, 2003, 61, 4, 529-537, https://doi.org/10.1016/S0039-9140(03)00319-9 . [all data]

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Zenkevich, I.G., New Application of the Retention Index Concept in Gas and High Performance Liquid Chromatography, Fresenius' J. Anal. Chem., 1999, 365, 4, 305-309, https://doi.org/10.1007/s002160051491 . [all data]

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Timón, M.L.; Ventanas, J.; Martín, L.; Tejeda, J.F.; García, C., Volatile compounds in supercritical carbon dioxide extracts of Iberian ham, J. Agric. Food Chem., 1998, 46, 12, 5143-5150, https://doi.org/10.1021/jf980652v . [all data]

Zenkevich, 1997
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Galindo-Cuspinera, Lubran, et al., 2002
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Pollak, F.C.; Berger, R.G., Geosmin and Related Volatiles in Bioreactor-Cultured Streptomyces citreus CBS 109.60, Appl. Environ. Microbiol., 1996, 62, 4, 1295-1299. [all data]

Kawakami, Ganguly, et al., 1995
Kawakami, M.; Ganguly, S.N.; Banerjee, J.; Kobayashi, A., Aroma composition of oolong tea and black tea by brewed extraction method and characterizing compounds of Darjeeling tea aroma, J. Agric. Food Chem., 1995, 43, 1, 200-207, https://doi.org/10.1021/jf00049a037 . [all data]

Kawakami and Kobayashi, 1991
Kawakami, M.; Kobayashi, A., Volatitle constituents of greem mate and roasted mate, J. Agric. Food Chem., 1991, 39, 7, 1275-1279, https://doi.org/10.1021/jf00007a016 . [all data]

Takeoka, Flath, et al., 1988
Takeoka, G.R.; Flath, R.A.; Güntert, M.; Jennings, W., Nectarine volatiles: vacuum steam distillation versus headspace sampling, J. Agric. Food Chem., 1988, 36, 3, 553-560, https://doi.org/10.1021/jf00081a037 . [all data]

Johanningsmeier and McFeeters, 2011
Johanningsmeier, S.D.; McFeeters, R.F., Detection of volatile spoilage metabolites in fermented cucumbers using nontargeted, comprehensive 2-dimensional gas chromatography-time-of-flight mass spectrometry (GCxGCxTOFMS), J. Food Sci., 2011, 76, 1, c168-c177, https://doi.org/10.1111/j.1750-3841.2010.01918.x . [all data]

Kaack and Christensen, 2008
Kaack, K.; Christensen, L.P., Effect of packing materials and storage time on volatile compounds in tea processes from flowers of black elder (Sambucus nigra L.), Eur. Food Res. Technol., 2008, 227, 4, 1259-1273, https://doi.org/10.1007/s00217-008-0844-8 . [all data]

Narain, Galvao, et al., 2007
Narain, N.; Galvao, M.S.; Madruga, M.S., Volatile compounds captured through purge and trap technique in caja-umbu (Spondias sp.) fruits during maturation, Food Chem., 2007, 102, 3, 726-731, https://doi.org/10.1016/j.foodchem.2006.06.003 . [all data]

Castioni and Kapetanidis, 1996
Castioni, P.; Kapetanidis, I., Volatile constituents from Brunfelsia grandiflora ssp. grandiflora: qualitative analysis by GC-MS, Scientia Pharmaceutica, 1996, 64, 83-91. [all data]


Notes

Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics data, Gas Chromatography, References