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Influence of Alkyl Groups in the Prototropic Change in Methyleneazomethines

Abstract

ARGUMENTS for and against control by either polar or steric effects of the course and rate of substitution and elimination reactions have recently been given1–3. The concept of steric assistance has been specially stressed as an important factor in determining relative rates of unimolecular eliminations of highly branched alkyl compounds3,4; in contrast to this positive steric factor, negative steric effects (connected with classical steric hindrance) play an important part in bimolecular nucleophilic substitution reactions5. It has been suggested3 that these steric effects can account for the known facts about nucleophilic substitutions and eliminations of alkyl compounds without need of special considerations regarding polar, particularly inductive, effects.

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References

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PÉREZ OSSORIO, R., GÓMEZ HERRERA, F. & MARTÍNEZ UTRILLA, R. Influence of Alkyl Groups in the Prototropic Change in Methyleneazomethines. Nature 179, 40 (1957). https://doi.org/10.1038/179040a0

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