Essential reactive intermediates in nucleoside chemistry: cyclonucleoside cationsElectronic supplementary information (ESI) available: Cartesian coordinates, energies, Wiberg indexes and atomic CHELPG charges of optimized structures as well as 1H, 13C NMR and HRMS spectral data of new compounds. See DOI: 10.1039/c2ob25868d

DFT-based modeling as well as experimental examination of model keto nucleosides have revealed that high susceptibility of these compounds to acids is due to formation of intermediate cyclonucleoside cations of low energy. Theoretically established chemical structures of these previously overlooked...

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Bibliographic Details
Main Authors: Belostotskii, Anatoly M, Genizi, Elisheva, Hassner, Alfred
Format: Article
Language:English
Online Access:Get full text
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Summary:DFT-based modeling as well as experimental examination of model keto nucleosides have revealed that high susceptibility of these compounds to acids is due to formation of intermediate cyclonucleoside cations of low energy. Theoretically established chemical structures of these previously overlooked intermediates explain the reaction courses for a cluster of nucleoside reactions. Cyclonucleoside cations are reactive intermediates in a broad group of nucleoside reactions.
ISSN:1477-0520
1477-0539
DOI:10.1039/c2ob25868d