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Relationship between nucleophilicity/electrophilicity indices and reaction mechanisms for the nucleophilic substitution reactions of carbonyl compounds
Author(s) -
Campodonico Paola,
Santos José G.,
Andres Juan,
Contreras Renato
Publication year - 2004
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.719
Subject(s) - chemistry , nucleophile , electrophile , reactivity (psychology) , substitution reaction , reagent , computational chemistry , reaction mechanism , nucleophilic substitution , organic chemistry , catalysis , medicine , alternative medicine , pathology
Theoretical electrophilicity and nucleophilicity scales, defined in terms of electronic reactivity indices, were tested for the reaction of a series of carbonates with neutral and charged reagents of varying nucleophilicity. The electrophilicity and nucleophilicity scales were used to rationalize some mechanistic aspects developed by these reacting systems: the greater the electrophilicity/nucleophilicity difference, the more concerted the reaction mechanism will be. Conversely, a small electrophilicity/nucleophilicty gap will in general be associated with a stepwise reaction mechanism. Copyright © 2004 John Wiley & Sons, Ltd.

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