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.
This is a preview of subscription content, access via your institution
Access options
Subscribe to this journal
Receive 51 print issues and online access
$199.00 per year
only $3.90 per issue
Buy this article
- Purchase on SpringerLink
- Instant access to full article PDF
Prices may be subject to local taxes which are calculated during checkout
Similar content being viewed by others
References
Brown, H. C., and Fletcher, R. S., J. Amer. Chem. Soc., 72, 1223 (1950).
Hughes, E. D., Ingold, C. K., and Shiner, jun., V. J., J. Chem. Soc., 3827 (1953).
Brown, H. C., J. Chem. Soc., 1248 (1956).
Brown, H. C., et al., J. Amer. Chem. Soc., 77, 3607 (1955), and subsequent papers.
Ingold, C. K., “Structure and Mechanism in Organic Chemistry”, 403 (Cornell Univ. Press, Ithaca, N.Y., 1953).
Pérez Ossorio, R., and Hughes, E. D., J. Chem. Soc., 426 (1952).
Pérez Ossorio, R., and Gómez Herrera, F., Anal. Fís. y Quím., 50 B, 875 (1954).
Pérez Ossorio, R., Gómez Herrera, F., and Hidalgo, A., Anal. Fís. y Quím., 52 B, 123 (1956).
Alemany, A. (work in progress).
Pérez Ossorio, R., Gamboa, J. M., and Martínez Utrilla, R. (in the press).
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
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
Issue date:
DOI: https://doi.org/10.1038/179040a0