β-Cyanoethyl Anion: Lusus Naturae

GN Merrill, GD Dahlke, SR Kass

Index: Merrill, Grant N.; Dahlke, Gregg D.; Kass, Steven R. Journal of the American Chemical Society, 1996 , vol. 118, # 18 p. 4462 - 4468

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Citation Number: 16

Abstract

A stable E1cb intermediate, β-cyanoethyl anion (1 β), 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 1 β by 29±6 kcal/mol, which represents a particularly large substituent effect. High-level ab initio and density functional ...