Reactive species: Ynols and ynamines

Acetylenic alcohols—ynols—and acetylenic amines—ynamines—have been generated in aqueous solution by flash phololytic decarbonylation of hydroxy‐ and aminocyclopropenones and their chemistry has been examined in that medium. This has revealed a remarkably strong acid‐strengthening effect of the acety...

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Bibliographic Details
Published inJournal of physical organic chemistry Vol. 9; no. 6; pp. 361 - 370
Main Authors Chiang, Y., Kresge, A. J., Paine, S. W., Popik, V. V.
Format Journal Article
LanguageEnglish
Published Chichester, UK John Wiley & Sons, Ltd 01.06.1996
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Summary:Acetylenic alcohols—ynols—and acetylenic amines—ynamines—have been generated in aqueous solution by flash phololytic decarbonylation of hydroxy‐ and aminocyclopropenones and their chemistry has been examined in that medium. This has revealed a remarkably strong acid‐strengthening effect of the acetylenic group, which ab initio molecular orbital calculations suggest results from a combination of destabilizing inductive effects on the initial state and stabilizing resonance effects on the final state of the acid ionization reaction.
Bibliography:Natural Sciences and Engineering Research Council
ArticleID:POC793
United States National Institutes of Health
istex:2998B57FFD0DF2096A4826C64C5B452977A39115
ark:/67375/WNG-FZTJ89J6-J
ISSN:0894-3230
1099-1395
DOI:10.1002/(SICI)1099-1395(199606)9:6<361::AID-POC793>3.0.CO;2-Y