trans Deformation of a Carbon-Carbon Triple Bond in Response to Incipient Nucleophilic Attack: The X-Ray Crystal Structure of Ethyl 3-(2-Nitrophenyl)propynoate at 150 K

Craig R. Rice, John D. Wallis

Research output: Contribution to journalArticle

7 Citations (Scopus)


In the title compound 1 the electron-deficient alkyne bond shows a pronounced trans distortion in response to an adjacent electron rich nitro O atom, suggesting that the more favourable reaction coordinate for addition of nucleophiles to activated alkynes involves trans rather than cis addition.

Original languageEnglish
Pages (from-to)572-574
Number of pages3
JournalJournal of the Chemical Society, Chemical Communications
Issue number6
Publication statusPublished - 1993
Externally publishedYes


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