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Reactive species: Ynols and ynamines
Author(s) -
Chiang Y.,
Kresge A. J.,
Paine S. W.,
Popik V. V.
Publication year - 1996
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/(sici)1099-1395(199606)9:6<361::aid-poc793>3.0.co;2-y
Subject(s) - chemistry , decarbonylation , ab initio , computational chemistry , aqueous solution , ionization , organic chemistry , molecular orbital , inductive effect , photochemistry , molecule , catalysis , ion
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.