Synthesis, structural, spectroscopic and electrochemical studies of carborane substituted naphthyl selenides

[EN] New unsymmetrical selenides bearing an o-carborane and a naphthalene ring as the substituents were prepared by the cleavage of the corresponding diselenides. The compounds were characterized by means of spectroscopic and analytical methods. Se-77 NMR signals of the selenium atoms attached to the carbon atoms of the carborane cages are shifted downfield in comparison to those bonded only to the aromatic rings, indicating an electron withdrawing effect of the o-carboranyl substituent. Compounds 1-(2-R-1,2-dicarba-closo-carboranyl)naphthyl selenides (R = Me, 1; Ph, 2) were characterized by means of single crystal X-ray diffraction. The influence of the electronic nature of the substituents attached to the selenium atoms on the structural parameters and packing properties of naphthyl selenides are discussed. Theoretical calculations and cyclic voltammetry (CV) studies were carried out to compare the bonding nature of carboranyl and analogous aryl selenium compounds. Cyclic voltammetry studies of naphthyl carboranyl mono and diselenides have shown that the carboranyl fragment polarizes the Se lone pair making it less prone to generate a Se-Se bond.This work was supported by the Japan-Spain Research Cooperative Program, Joint Project, 2004JP0102 from Japan Society for the Promotion of Science (JSPS) and CSIC, CICYT (CTQ2010-16237) and the Generalitat de Catalunya, 2009/SGR/00279. Dr O. Guzyr is grateful to Ministerio Education, Cultura y Deporte for grant SAB2003-0122.Guzyr, O.; Viñas, C.; Wada, H.; Hayashi, S.; Nakanishi, W.; Teixidor, F.; Vaca Puga, A.... (2011). Synthesis, structural, spectroscopic and electrochemical studies of carborane substituted naphthyl selenides. Dalton Transactions. 40(13):3402-3411. https://doi.org/10.1039/c0dt01658f34023411401