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Focus on Chemistry of the 10-Dioxane-nido-7,8-dicarba-undecahydrido Undecaborate Zwitterion, Exceptionally Easy Abstraction of Hydrogen Bridge and Double-Action Pathways Observed in Ring Cleavage Reactions with OH- as Nucleophile
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SYSNO ASEP 0523804 Document Type J - Journal Article R&D Document Type Journal Article Subsidiary J Článek ve WOS Title Focus on Chemistry of the 10-Dioxane-nido-7,8-dicarba-undecahydrido Undecaborate Zwitterion, Exceptionally Easy Abstraction of Hydrogen Bridge and Double-Action Pathways Observed in Ring Cleavage Reactions with OH- as Nucleophile Author(s) Bakardjiev, Mario (UACH-T) SAI, RID
El Anwar, Suzan (UACH-T) SAI, ORCID, RID
Bavol, Dmytro (UACH-T) SAI, RID, ORCID
Růžičková, Z. (CZ)
Grüner, Bohumír (UACH-T) RID, SAI, ORCIDNumber of authors 5 Article number 814 Source Title Molecules. - : MDPI
Roč. 25, č. 4 (2020)Number of pages 20 s. Language eng - English Country CH - Switzerland Keywords borane ; carborane ; dicarbollide ion ; oxonium atom ; nucleophilic substitution Subject RIV CA - Inorganic Chemistry OECD category Inorganic and nuclear chemistry R&D Projects GA18-27648S GA ČR - Czech Science Foundation (CSF) Method of publishing Open access Institutional support UACH-T - RVO:61388980 UT WOS 000522454500050 EID SCOPUS 85079667167 DOI 10.3390/molecules25040814 Annotation Ring cleavage of cyclic ether substituents attached to a boron cage via an oxonium oxygen atom are amongst the most versatile methods for conjoining boron closo-cages with organic functional groups. Here we focus on much less tackled chemistry of the 11vertex zwitterionic compound [10-(0-(CH2-CH2)(2)O)-nido-7,8-C2B9H11] (1), which is the only known representative of cyclic ether substitution at nido-cages, and explore the scope for the use of this zwitterion 1 in reactions with various types of nucleophiles including bifunctional ones. Most of the nitrogen, oxygen, halogen, and sulphur nucleophiles studied react via nucleophilic substitution at the C1 atom of the dioxane ring, followed by its cleavage that produces six atom chain between the cage and the respective organic moiety. We also report the differences in reactivity of this nido-cage system with the simplest oxygen nucleophile, i.e., OH-. With compound 1, reaction proceeds in two possible directions, either via typical ring cleavage, or by replacement of the whole dioxane ring withOH at higher temperatures. Furthermore, an easy deprotonation of the hydrogen bridge in 1 was observed that proceeds even in diluted aqueous KOH. We believe this knowledge can be further applied in the design of functional molecules, materials, and drugs. Workplace Institute of Inorganic Chemistry Contact Jana Kroneislová, krone@iic.cas.cz, Tel.: 311 236 931 Year of Publishing 2021 Electronic address http://hdl.handle.net/11104/0308097
Number of the records: 1