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• W2000051038 startingPage "3629" @default.
• W2000051038 abstract "Abstract The reactivity of disulfide and diselenide derivatives towards F − and CN − nucleophiles has been investigated by means of B3PW91/6‐311+G(2df,p) calculations. This theoretical survey shows that these processes, in contrast with the generally accepted view of disulfide and diselenide linkages, do not always lead to SS or SeSe bond cleavage. In fact, SS or SeSe bond fission is the most favorable process only when the substituents attached to the S or the Se atoms are not very electronegative. Highly electronegative substituents (X) strongly favor SX bond fission. This significant difference in the observed reactivity patterns is directly related to the change in the nature of the LUMO orbital of the disulfide or diselenide derivative as the electronegativity of the substituents increases. For weakly electronegative substituents, the LUMO is a σ‐type SS (or SeSe) antibonding orbital, but as the electronegativity of the substituents increases the π‐type SX antibonding orbital stabilizes and becomes the LUMO. The observed reactivity also changes with the nature of the nucleophile and with the S or Se atom that undergoes the nucleophilic attack in asymmetric disulfides and diselenides. The activation strain model provides interesting insights into these processes. There are significant similarities between the reactivity of disulfides and diselenides, although some dissimilarities are also observed, usually related to the different interaction energies between the fragments produced in the fragmentation process." @default.
• W2000051038 created "2016-06-24" @default.
• W2000051038 creator A5050371831 @default.
• W2000051038 creator A5057170191 @default.
• W2000051038 creator A5061295554 @default.
• W2000051038 creator A5071111073 @default.
• W2000051038 date "2013-01-29" @default.
• W2000051038 modified "2023-10-18" @default.
• W2000051038 title "Revealing Unexpected Mechanisms for Nucleophilic Attack on SS and SeSe Bridges" @default.
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• W2000051038 doi "https://doi.org/10.1002/chem.201203328" @default.
• W2000051038 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/23361893" @default.
• W2000051038 hasPublicationYear "2013" @default.
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