The reaction of tetrakis(thf)lithium dimesityl-1,8-naphthalenediylborate with either Ph₂ SbCl or Ph₂BiCl afforded 1-(diphenylantimony)-8-(dimesitylboron)naphthalenediyl (1) and 1-(diphenylbismuth)-8-(dimesitylboron) naphthalenediyl (2). These unprecedented boron/antimony and boron/bismuth derivatives have been characterized by multinuclear NMR spectroscopy, elemental analysis, and X-ray single-crystal analysis. The latter reveals that the 1,8-naphthalenediyl backbone enforces short E→B (E = Sb, Bi) distances of 3.216 Å for 1 and 3.330 Å for 2. Natural bond order studies indicate that these short contacts are associated to lp(E)→p(B) interactions, which contribute to the stability of the compounds by 8.65 kcal/mol⁻¹ in the case of 1 and 6.32 kcal/mol⁻¹ in the case of 2. © 2011 Wiley Periodicals, Inc. Heteroatom Chem 22:500–505, 2011; View this article online at wileyonlinelibrary.com. DOI 10.1002/hc.20713

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Synthesis and structure of peri-substituted boron/pnictogen naphthalene derivatives^†

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Synthesis and structure of peri-substituted boron/pnictogen naphthalene derivatives^†