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Nucleophilic substitution at saturated carbon atoms. Mechanisms and mechanistic borderlines: Evidence from studies with neutral leaving groups
Author(s) -
Katritzky Alan R.,
Brycki Bogumil E.
Publication year - 1988
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.610010103
Subject(s) - chemistry , solvolysis , alkyl , nucleophilic substitution , sn1 reaction , nucleophile , merge (version control) , leaving group , substitution reaction , primary (astronomy) , molecule , photochemistry , computational chemistry , organic chemistry , hydrolysis , catalysis , physics , astronomy , computer science , information retrieval
Abstract Substrates with neutral leaving groups undergo unimolecular solvolysis in nonpolar solvents. Whereas t ‐alkyl substrates invariably solvolyze by a unimolecular mechanism, s ‐alkyl and primary alkyl substrates can undergo both uni and bimolecular reactions, and the bimolecular step can take place on either the substrate itself or on an intimate ion‐molecule pair formed in either a pre‐equilibrium or in a rate determining step. Study of reactions at borderlines indicates that the individual reaction types remain distinct and do not merge.