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The Bullvalene Story. The Conception of Bullvalene, a Molecule That Has No Permanent Structure

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Addison Ault

Department of Chemistry, Cornell College, Mount Vernon, IA 52314

J. Chem. Educ., 2001, 78 (7), p 924

DOI: 10.1021/ed078p924

Publication Date (Web): July 1, 2001

Section:

History, Education, and Documentation

Abstract

In this paper I review and summarize the logical process through which Doering and Roth (Tetrahedron 1963, 19, 715) conceived of the possible existence of an isomer of molecular formula C₁₀H₁₀ that has a "fluxional" structure. That is, the molecule has a structure in which every carbon atom is equally bonded, or not bonded, to every other carbon. The evidence for its "fluxional" structure is that it gives a sharp singlet in its proton NMR spectrum. In order for the 10 protons, each bonded to a carbon atom, to be chemical-shift equivalent, Doering and Roth conclude that "all ten carbon atoms [must] inevitably wander over the surface of a sphere in ever changing relationship to each other."

Keywords (Audience):

Second-Year Undergraduate

Keywords (Domain):

History / Philosophy

Keywords (Subject):

Molecular Properties / Structure

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