A theoretical and experimental study of the racemization process of hexaaza[5]helicenes |
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| Authors: | Belén Abarca Rafael Ballesteros Rosa Adam Rafael Ballesteros-Garrido Frédéric R Leroux Françoise Colobert Ibon Alkorta José Elguero |
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| Institution: | 1. Departamento de Química Orgánica, Facultad de Farmacia, Universidad de Valencia, Avd. Vte. Andrés Estellés s/n, 46100 Burjassot, Valencia, Spain;2. Laboratoire de Stéréochimie, CNRS, Université de Strasbourg (ECPM), 25 rue Becquerel, 67087 Strasbourg, France;3. Instituto de Química Médica (CSIC), Juan de la Cierva 3, E-28006 Madrid, Spain |
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| Abstract: | 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. |
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| Keywords: | Azahelicenes Helical chirality Diazoimine&ndash triazole equilibrium Racemization barriers |
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