β-Cyanoethyl anion: Lusus naturae

Grant N. Merrill, Gregg D. Dahlke, Steven R Kass

Research output: Contribution to journalArticlepeer-review

15 Scopus citations

Abstract

A stable El(cb) intermediate, β-cyanoethyl anion (1β), has been synthesized in the gas phase at room temperature under thermal conditions via the fluoride-induced desilylation of 3-(trimethylsilyl)propionitrile. The reactivity and thermodynamic properties of this ion are reported. The cyano group is found to lower the proton affinity of 1β by 29 ± 6 kcal/mol, which represents a particularly large substituent effect. High-level ab initio and density functional calculations have been carried out on 1β and several related species. The computational results are compared to each other, and their accuracy is evaluated.

Original languageEnglish (US)
Pages (from-to)4462-4468
Number of pages7
JournalJournal of the American Chemical Society
Volume118
Issue number18
DOIs
StatePublished - Jan 1 1996

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