Structure and Bonding in Bis(1‐naphthyl) Diselenide and Bis{[2‐(N,N‐dimethylamino)methyl]phenyl} Tetraselenide, and Their Brominated Derivatives

Abstract

Abstract. The formation and crystal structures of bis(1-naphthyl) diselenide (1) and bis{ [2-(N,N-dimethylamino)methyl]phenyl} tetraselenide (2) are described. Whereas 1 can be produced in good yields, 2 is formed only as a minor product together with the known main product, bis{[2-(N,N-dimethylamino)methyl]phenyl} diselenide. The composition of the reaction mixture is semi-quantitatively estimated by 77 Se NMR spectroscopy and DFT calculations. The effect of the

Chalcogen bonding in synthesis, catalysis and design of materials

“…80 Another interesting motif that relies upon a 1,5 N⋯Se interaction was encountered in the single-crystal X-ray structure of bis{[2-(N,N-dimethylamino)methyl]phenyl}tetraselenide, obtained by the treatment of N,N-dimethylbenzylamine with n-butyllithium and elemental selenium, followed by oxidation under aqueous conditions (Scheme 9). 81 The formation of the two five-membered cycles with the assistance of intramolecular chalcogen bonding results in the production of the corresponding organotetraselenide compound (Scheme 9).…”

Main group metal lone-pair⋯π(arene) interactions: a new bonding mode for supramolecular associations

“…1_V, arises in the crystal structure of 122. 123 Here, binuclear molecules with 2-fold symmetry, self-associate about centres of inversion to form twisted chains, Fig. 18g.…”

The synthesis and crystal structure of 2-(chloroselanyl)pyridine 1-oxide: the first monomeric organoselenenyl chloride stabilized by an intramolecular secondary Se...O interaction

“…Organoselenenyl halides RSeX (X = Cl, Br) play an important role in modern organic synthesis and are used as reagents for the functionalization of many classes of compounds, including organoselenium compounds with a broad spectrum of biological activities (Ranganathan et al, 2004;Selvakumar et al, 2010Selvakumar et al, , 2011Ninomiya et al, 2011;Singh & Wirth, 2011;Zade & Singh, 2014;Elsherbini et al, 2016). An essential aspect of the chemistry of selenenyl halides is the factors responsible for the stability of these reagents (Coles, 2006;Mukherjee et al, 2010;Nakanishi et al, 2013;Takaluoma et al, 2015). Recently, we have developed a new effective method for the stabilization of heteroarenselenenyl and -tellurenyl chlorides by the transformation of them to T-shaped zwitterionic adducts with hydrochloric acid (Khrustalev et al, 2012(Khrustalev et al, , 2014(Khrustalev et al, , 2016.…”