6533b82dfe1ef96bd1291f9c
RESEARCH PRODUCT
From Mono- to Poly-Substituted Frameworks: A Way of Tuning the Acidic Character of C-c-H in o-Carborane Derivatives
Clara ViñasGemma BarberàReijo SillanpääFrancesc TeixidorRaikko KivekäsMassimiliano ArcaAlberto V. Pugasubject
inorganic chemicalsNatural bond orbital chargesInorganic chemistrychemistry.chemical_elementElectron010402 general chemistryIodine01 natural sciencesCatalysisQUIMICA ANALITICACluster (physics)BoronCarboranesBoron010405 organic chemistryOrganic ChemistryGeneral ChemistryNuclear magnetic resonance spectroscopy3. Good health0104 chemical sciencesCrystallographyDensity functional calculationschemistryCarboraneCarbonNatural bond orbitalIodinedescription
[EN] The incorporation of iodine atoms onto the boron vertices of the o-carborane framework causes, according to spectroscopic data, a uniform increase in the acidic character of the C-c-H (C-c= cluster carbon) vertices, whereas the incorporation of methyl groups onto the boron vertices of the o-carborane framework reduces their acidity. Methyl groups when attached to boron are electron-withdrawing in boron clusters, whereas iodine atoms bonded to boron act as electron donors. This has been proven on B-methyl and B-iodinated o-carboranes with NMR spectroscopy measurements and DFT calculations of natural bond orbital (NBO) charges. which show a Cumulative buildup of positive cluster only total charge (CTC) on B-methyl o-carboranes and a cumulative buildup of negative cluster-only total charge for B-iodinated o-carboranes.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2009-01-01 |