Synthesis and Structure of Peri-Substituted Boron/Pnictogen Naphthalene Derivatives Academic Article uri icon

abstract

  • 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 EB (E = Sb, Bi) distances of 3.216 for 1 and 3.330 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.

published proceedings

  • HETEROATOM CHEMISTRY

author list (cited authors)

  • Wade, C. R., Saber, M. R., & Gabbai, F. P.

citation count

  • 17

complete list of authors

  • Wade, Casey R||Saber, Mohamed R||Gabbaii, Francois P

publication date

  • May 2011

publisher