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Vinyl alcohol : ウィキペディア英語版
Vinyl alcohol

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Vinyl alcohol, also called ethen-1-ol (IUPAC name), is an alcohol. It is not to be confused with the drinking alcohol, ethanol. With the formula 2CHH, vinyl alcohol is an isomer of acetaldehyde and ethylene oxide. Under normal conditions, it converts (tautomerizes) to acetaldehyde:
:
==Tautomerization of acetaldehyde to vinyl alcohol==
At room temperature, acetaldehyde (H3CC(O)H) is more stable than vinyl alcohol (H2C=CHOH) by 42.7 kJ/mol:〔(【引用サイトリンク】title=CCCBDB NIST Standard Reference Database. )
H2C=CHOH → H3CC(O)H ∆''H''298,g = –42.7 kJ/mol
This keto-enol tautomerization has a high barrier and does therefore not occur near room temperature. This tautomerization can be catalyzed via photochemical process. These findings suggest that the keto-enol tautomerization is a viable route under atmospheric and stratospheric conditions, relevant to a role for vinyl alcohol in the production of organic acids in the atmosphere.〔Heazlewood, B. R.; Maccarone, A. T.; Andrews, D. U.; Osborn, D. L.; Harding, L. B.; Klippenstein, S. J.; Jordan, M. J. T.; Kable, S. H. "Near-threshold H/D exchange in CD3CHO photodissociation." Nat. Chem. 2011, 3, 443−448. 〕〔Andrews, D. U.; Heazlewood, B. R.; Maccarone, A. T.; Conroy, T.; Payne, R. J.; Jordan, M. J. T.; Kable, S. H. "Photo-tautomerization of acetaldehyde to vinyl alcohol: A potential route to tropospheric acids." Science 2012, 337, 1203−1206. 〕

抄文引用元・出典: フリー百科事典『 ウィキペディア(Wikipedia)
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