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Bullvalene: Reaction Graphs for Rearrangements of Heteroatomic and Substituted Positional Isomers

Benjamin M. Gimarc ; Department of Chemistry, University of South Carolina, Columbia, SC 29208
Jane J. Ott ; Department of Chemistry, Furman University, Greenville, SC 29613

Sažetak

Those of us who have faith in molecular structures are mocked by the fluxional behavior of the bullvalene molecule in which each of the 10 framework atoms is free to move through all possible positions in the structure. Indeed, there are 1,209,600 possible permutational isomers of bullvalene. But the situation simplifies enormously if we replace one or more carbons by heteroatoms or exo-hydrogens by other substituents and then consider only positional isomers. For example, bullvalene with a single cage heteroatom or substituent has only four different positional isomers. Rearrangements involving positional isomers can be conveniently represented by a reaction graph in which the vertices correspond to individual isomers and the edges stand for processes that carry one isomer into another. The different energies of the isomers can be estimated by the rule of topological charge stabilization. In this paper, reaction graphs and relative isomer energies are used to rationalize previously reported experimental observations of isomerizations of heteroatomic and substituted bullvalenes.

Ključne riječi

Hrčak ID:

137326

URI

https://hrcak.srce.hr/137326

Datum izdavanja:

31.12.1991.

Posjeta: 1.318 *