2024-03-28T12:58:13Zhttp://digital.csic.es/dspace-oai/requestoai:digital.csic.es:10261/1080162021-10-27T11:57:19Zcom_10261_81com_10261_5col_10261_334
A theoretical and experimental study of the racemization process of hexaaza[5]helicenes
Abarca, B.
Ballesteros, R.
Adam, Rosa
Ballesteros-Garrido, R.
Leroux, Frédérc R.
Colobert, François
Alkorta, Ibon
Elguero, José
Diazoimine–triazole equilibrium
Racemization barriers
Helical chirality
Azahelicenes
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.
We are grateful to the Ministerio de Ciencia e Innovacion (Spain) (Project CONSOLIDER-INGENIO SUPRAMED CSD 2010-00065), to Generalitat Valenciana (Valencia, Spain) (project PROMETEO 2011/ 008) for its financial support, to the SCSIE for the realization of HRMS spectra and Prof. Salvador Garrigues for the realization of IR spectrum of compound 2. Thanks are also given to the Ministerio de Economía y Competitividad of Spain (Project CTQ2012-13129-C02- 02) and the Comunidad Autonoma de Madrid (Project MADRISOLAR2, ref. S2009/PPQ-1533).
Peer Reviewed
2014-11-25T11:12:53Z
2014-11-25T11:12:53Z
2014
2014-11-25T11:12:53Z
artículo
http://purl.org/coar/resource_type/c_6501
doi: 10.1016/j.tet.2014.09.018
issn: 1464-5416
Tetrahedron 70: 8750-8757 (2014)
http://hdl.handle.net/10261/108016
10.1016/j.tet.2014.09.018
none
Elsevier