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The Electrophilic Reactivity of Tetrabromorhodamine 123 is Bromine Induced: Convergent Interpretation through Complementary Molecular Descriptors.
MedLine Citation:
PMID:  23134615     Owner:  NLM     Status:  Publisher    
Abstract/OtherAbstract:
Nucleophilic addition of water and of methanol to 3,6-diamino-2,4,5,7-tetrabromo-9-[2-(methoxycarbonyl) phenyl]-9H-xanthen-9-ylium, 4BrR123, yields, respectively, xanthyl, 2-(3,6-diamino-2,4,5,7-tetrabromo-9-hydroxy-9H-xanthen-9-yl) benzoate, HO4BrR123 and, xanthyl, 2-(3,6-diamino-2,4,5,7-tetrabromo-9-methoxy-9H-xanthen-9-yl) benzoate, MeO4BrR123. The novel experimental results are addressed theoretically. The Linear Free Energy Relationship, LFER, Second Order Perturbation Theory analysis of the Natural Bond Orbital, NBO, and Quantum Theory of Atoms in Molecules, QTAIM, lead to the same conclusion: the electron-withdrawing effect of bonded Br atoms in 4BrR123 enhances extremely molecular electrophilicity, as compared to 3,6-diamino-9-[2-(methoxycarbonyl) phenyl]-9H-xanthen-9-ylium, R123. The reactivity of these diaminoxanthylium cations is discussed in the context of local and global softness in extended conjugated systems.
Authors:
José A B Ferreira; Antonio Sánchez-Coronilla; Denisio M Togashi; Humberto Ferreira; José Rosário Ascenso; Silvia M B Costa
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Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2012-11-7
Journal Detail:
Title:  The journal of physical chemistry. A     Volume:  -     ISSN:  1520-5215     ISO Abbreviation:  J Phys Chem A     Publication Date:  2012 Nov 
Date Detail:
Created Date:  2012-11-8     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  9890903     Medline TA:  J Phys Chem A     Country:  -    
Other Details:
Languages:  ENG     Pagination:  -     Citation Subset:  -    
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