Acetic acid ethenyl ester
- Formula: C4H6O2
- Molecular weight: 86.0892
- IUPAC Standard InChIKey: XTXRWKRVRITETP-UHFFFAOYSA-N
- CAS Registry Number: 108-05-4
- 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. - Other names: Acetic acid vinyl ester; Vinyl acetate; Vinyl A monomer; VyAc; 1-Acetoxyethylene; CH3CO2CH=CH2; Ethenyl acetate; Ethenyl ethanoate; Acetate de vinyle; Ethanoic acid, ethenyl ester; Octan winylu; Vinile (acetato di); Vinyl acetate h.q.; Vinyl ethanoate; Vinylacetaat; Vinylacetat; Vinyle (acetate de); Zeset T; Acetic acid, ethylene ether; VAC; Vinylester kyseliny octove; Vinyl ester of acetic acid; Everflex 81L; Plyamul 40305-00; Unocal 76 Res 6206; Unocal 76 Res S-55; Vinnapas A 50; Vinyl acetate monomer; Acetoxyethene; NSC 8404
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Gas phase ion energetics data
Go To: Top, Mass spectrum (electron ionization), 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:
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
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
IE (evaluated) | 9.2 | eV | N/A | N/A | L |
Quantity | Value | Units | Method | Reference | Comment |
Proton affinity (review) | 813.9 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 782.9 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
9.2 | PE | Van Dam and Oskam, 1978 | LLK |
9.19 ± 0.05 | PI | Watanabe, Nakayama, et al., 1962 | RDSH |
9.85 | PE | Van Dam and Oskam, 1978 | Vertical value; LLK |
9.85 ± 0.05 | PE | Houk and Munchausen, 1976 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C2H3O+ | 10.04 ± 0.05 | C2H3O | EI | Holmes and Lossing, 1986 | LBLHLM |
Mass spectrum (electron ionization)
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 by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Spectrum
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Additional Data
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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-5546 |
NIST MS number | 228294 |
Gas Chromatography
Go To: Top, Gas phase ion energetics data, 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.
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 |
---|---|---|---|---|---|
Packed | SE-30 | 100. | 564. | Winskowski, 1983 | Gaschrom Q; Column length: 2. m |
Packed | Apiezon L | 120. | 527. | Bogoslovsky, Anvaer, et al., 1978 | Celite 545 |
Packed | Apiezon L | 160. | 529. | Bogoslovsky, Anvaer, et al., 1978 | Celite 545 |
Packed | SE-30 | 150. | 545. | Allen and Haken, 1970 | Celite 560 silanized; Column length: 3.7 m |
Packed | SE-30 | 150. | 548. | Germaine and Haken, 1969 | Celite 560; Column length: 3.7 m |
Normal alkane RI, non-polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Capillary | SE-30 | 120. | 524. | Gröbler and Bálizs, 1981 | |
Packed | Synachrom | 150. | 546. | Dufka, Malinsky, et al., 1971 | Helium, Synachrom (60-80 mesh); Column length: 1.5 m |
Packed | Synachrom | 150. | 551. | Dufka, Malinsky, et al., 1971 | Helium, Synachrom (60-80 mesh); Column length: 1.5 m |
Packed | DC-400 | 150. | 570. | Anderson, 1968 | Helium, Gas-Pak (60-80 mesh); Column length: 3.0 m |
Normal alkane RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | OV-101 | 570. | Zenkevich, 2005 | 25. m/0.20 mm/0.10 μm, N2/He, 6. K/min; Tstart: 50. C; Tend: 250. C |
Capillary | BP-1 | 560. | Health Safety Executive, 2000 | 50. m/0.22 mm/0.75 μm, He, 5. K/min; Tstart: 50. C; Tend: 200. C |
Normal alkane RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | SE-30 | 562. | Vinogradov, 2004 | Program: not specified |
Capillary | DB-1 | 562. | Ciccioli, Cecinato, et al., 1994 | 60. m/0.32 mm/0.25 μm; Program: not specified |
Capillary | DB-1 | 562. | Ciccioli, Brancaleoni, et al., 1993 | 60. m/0.32 mm/0.25 μm; Program: 3 min at 5 C; 5 - 50 C at 3 deg/min; 50 - 220 C at 5 deg/min |
Capillary | OV-1, SE-30, Methyl silicone, SP-2100, OV-101, DB-1, etc. | 548. | Waggott and Davies, 1984 | Hydrogen; Column length: 50. m; Column diameter: 0.32 mm; Program: not specified |
Capillary | OV-1, SE-30, Methyl silicone, SP-2100, OV-101, DB-1, etc. | 564. | Waggott and Davies, 1984 | Hydrogen; Column length: 50. m; Column diameter: 0.32 mm; Program: not specified |
Normal alkane RI, polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Carbowax 20M | 878. | Vinogradov, 2004 | Program: not specified |
References
Go To: Top, Gas phase ion energetics data, Mass spectrum (electron ionization), Gas Chromatography, 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]
Van Dam and Oskam, 1978
Van Dam, H.; Oskam, A.,
He(I) and He(II) photoelectron spectra of some substituted ethylenes,
J. Electron Spectrosc. Relat. Phenom., 1978, 13, 273. [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]
Houk and Munchausen, 1976
Houk, K.N.; Munchausen, L.L.,
Ionization potentials, electron affinities, reactivities of cyanoalkenes related electron-deficient alkenes. A frontier molecular orbital treatment of cyanoalkene reactivities in cycloaddition, electrophilic, nucleophilic, and radical reactions.,
J. Am. Chem. Soc., 1976, 98, 937. [all data]
Holmes and Lossing, 1986
Holmes, J.L.; Lossing, F.P.,
Heats of formation and homolytic bond dissociation energies in the keto-enol tautomers C2H4O, C3H6O,
J. Am. Chem. Soc., 1986, 108, 1086. [all data]
Winskowski, 1983
Winskowski, J.,
Gaschromatographische Identifizierung von Stoffen anhand von Indexziffem und unterschiedlichen Detektoren,
Chromatographia, 1983, 17, 3, 160-165, https://doi.org/10.1007/BF02271041
. [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]
Allen and Haken, 1970
Allen, I.D.; Haken, J.K.,
Gas chromatography of homologous esters. Part IV. Influence of stationary phase polarity on retention of unsaturated esters,
J. Chromatogr., 1970, 51, 415-422, https://doi.org/10.1016/S0021-9673(01)96890-6
. [all data]
Germaine and Haken, 1969
Germaine, R.W.; Haken, J.K.,
Gas chromatography of homologous esters. Part 2. Unsaturated esters,
J. Chromatogr., 1969, 43, 43-47, https://doi.org/10.1016/S0021-9673(00)99163-5
. [all data]
Gröbler and Bálizs, 1981
Gröbler, A.; Bálizs, G.,
Investigations on mixed gas chromatographic stationary phases. Part 3: A generalized approximation of retention indices for polar-nonpoalar stationary phase mixtures,
J. Chromatogr. Sci., 1981, 19, 1, 46-51, https://doi.org/10.1093/chromsci/19.1.46
. [all data]
Dufka, Malinsky, et al., 1971
Dufka, O.; Malinsky, J.; Vladyka, J.,
Sorpcni materialy pro plynovou chromatographii - III,
Chemicky promysl., 1971, 21/46, 9, 459-463. [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]
Zenkevich, 2005
Zenkevich, I.G.,
Experimentally measured retention indices., 2005. [all data]
Health Safety Executive, 2000
Health Safety Executive,
MDHS 96 Volatile organic compounds in air - Laboratory method using pumed solid sorbent tubes, solvent desorption and gas chromatography
in Methods for the Determination of Hazardous Substances (MDHS) guidance, Crown, Colegate, Norwich, 2000, 1-24, retrieved from http://www.hse.gov.uk/pubns/mdhs/pdfs/mdhs96.pdf. [all data]
Vinogradov, 2004
Vinogradov, B.A.,
Production, composition, properties and application of essential oils, 2004, retrieved from http://viness.narod.ru. [all data]
Ciccioli, Cecinato, et al., 1994
Ciccioli, P.; Cecinato, A.; Brancaleoni, E.; Brachetti, A.; Frattoni, M.; Sparapani, R.,
Composition and Distribution of Polar and Non-Polar VOCs in Urban, Rural, Forest and Remote Areas,
Eur Commission EUR, 1994, 549-568. [all data]
Ciccioli, Brancaleoni, et al., 1993
Ciccioli, P.; Brancaleoni, E.; Cecinato, A.; Sparapani, R.; Frattoni, M.,
Identification and determination of biogenic and anthropogenic volatile organic compounds in forest areas of Northern and Southern Europe and a remote site of the Himalaya region by high-resolution gas chromatography-mass spectrometry,
J. Chromatogr., 1993, 643, 1-2, 55-69, https://doi.org/10.1016/0021-9673(93)80541-F
. [all data]
Waggott and Davies, 1984
Waggott, A.; Davies, I.W.,
Identification of organic pollutants using linear temperature programmed retention indices (LTPRIs) - Part II, 1984, retrieved from http://dwi.defra.gov.uk/research/completed-research/reports/dwi0383.pdf. [all data]
Notes
Go To: Top, Gas phase ion energetics data, Mass spectrum (electron ionization), Gas Chromatography, References
- Symbols used in this document:
AE Appearance energy IE (evaluated) Recommended ionization energy - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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