Relationship between nucleophilicity/electrophilicity indices and reaction mechanisms for the nucleophilic substitution reactions of carbonyl compounds | Zendy

Campodonico Paola | Zendy; Santos José G. | Zendy; Andres Juan | Zendy; Contreras Renato | Zendy

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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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