6533b86ffe1ef96bd12cd419
RESEARCH PRODUCT
A theoretical and experimental study of the racemization process of hexaaza[5]helicenes
Frédéric R. LerouxRafael Ballesteros-garridoFrançoise ColobertBelén AbarcaJosé ElgueroRosa AdamIbon AlkortaRafael Ballesterossubject
Helical chirality[CHIM.ORGA]Chemical Sciences/Organic chemistryStereochemistryPhenanthrolineOrganic ChemistryRing (chemistry)BiochemistryTautomer3. Good healthRacemization barrierschemistry.chemical_compoundAzahelicenesChain (algebraic topology)chemistryComputational chemistryDrug DiscoveryProton NMRDiazoimine–triazole equilibriumRacemizationdescription
A dynamic 1H NMR study, together with DFT calculations, of bis-([1,2,3]triazolo)[1,5-a:5′,1′-k][1,10]phenanthroline 2 has allowed to identify the ring and open forms of a new example of ring/chain tautomerism, as well as their interconversion barriers (ring/ring and ring/open). The barrier of the exchange process between the chain forms and the ring form was found higher than the 'racemization' process in the closed form, so the ring opening does not contribute to the 'racemization'. The di-1,10-methyl and di-1,10-iodo derivatives have been prepared and their properties calculated.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2014-11-01 | Tetrahedron |