Cyclobutane-bicyclobutane system. Part 10. Conformation and stability of 1-bicyclobutylcarbinyl anion

Shmaryahu Hoz; Rachel Levy

doi:10.1016/0166-1280(85)85055-7

Cyclobutane-bicyclobutane system. Part 10. Conformation and stability of 1-bicyclobutylcarbinyl anion

Shmaryahu Hoz, Rachel Levy

Department of Chemistry

Bar-Ilan University

Research output: Contribution to journal › Article › peer-review

3 Scopus citations

Abstract

The ability of a bicyclobutyl moiety to stabilize a negative charge at an α-position was investigated by analyzing the two conformers (parallel and orthogonal) of 1-bicyclobutyl-carbinyl anion. A study at a 4-31G level reveals that the two conformers are equally stabilized by the ring. While the parallel conformer is stabilized in an allylic-like fashion by the π-like bridge bond, the two side bonds effectively stabilize the carbanion in the orthogonal geometry.

Original language	English
Pages (from-to)	93-99
Number of pages	7
Journal	Journal of Molecular Structure: THEOCHEM
Volume	22
Issue number	1-5
DOIs	https://doi.org/10.1016/0166-1280(85)85055-7
State	Published - Mar 1985

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abstract = "The ability of a bicyclobutyl moiety to stabilize a negative charge at an α-position was investigated by analyzing the two conformers (parallel and orthogonal) of 1-bicyclobutyl-carbinyl anion. A study at a 4-31G level reveals that the two conformers are equally stabilized by the ring. While the parallel conformer is stabilized in an allylic-like fashion by the π-like bridge bond, the two side bonds effectively stabilize the carbanion in the orthogonal geometry.",

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Cyclobutane-bicyclobutane system. Part 10. Conformation and stability of 1-bicyclobutylcarbinyl anion

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