^(13)C, ^1H, and ^2H NMR Observation of Trideuterated Cyclopropylmethyl-Cyclobutyl Carbocation: A Configurationally Stable Species

Abstract

With the increasing power and sophistication of experimental and theoretical methods for assigning chemical structures, it seems almost incredible that the structure of any reasonably stable organic entity with a small number of carbons could remain enigmatic for very long. Nonetheless, this is true of C_4H_7^+-one of the first "nonclassical" cations to be discovered, which has some of the characteristics expected for a very rapidly equilibrating mixture of classical cyclopropylmethyl, cyclobutyl, and 3-butenyl cations and yet other characteristics which wholly belie any description that implies conventional charge distributions or geometries derived from structural representations using solid lines representing two-electron bonds.

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