%0 Generic %A Merrill, Grant N. %A Dahlke, Gregg D. %A Kass, Steven R. %D 1996 %T β-Cyanoethyl Anion:  Lusus Naturae %U https://acs.figshare.com/articles/dataset/_-Cyanoethyl_Anion_Lusus_Naturae/3658719 %R 10.1021/ja953796o.s001 %2 https://acs.figshare.com/ndownloader/files/5748429 %K ab %K calculation %K proton %K Cyanoethyl %K species %K desilylation %K density %K 1 β %K reactivity %K affinity %K cyanoethyl %K cyano %K accuracy %K Anion %K initio %K Naturae %K ion %K trimethylsilyl %K phase %K substituent %K anion %K Lusu %K E 1 cb %K kcal %X A stable E1cb 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. %I ACS Publications