Synthesis, structure, and bonding of stable dialkylsilaketenimines

Takashi Abe, Takeaki Iwamoto, Chizuko Kabuto, Mitsuo Kira

Research output: Contribution to journalArticlepeer-review

48 Citations (Scopus)

Abstract

Stable (N-aryl)- and (N-alkyl)dialkylsilaketenimines R2SiCNR′ [R = 1,1,4,4-tetrakis(trimethylsilyl)butane-1,4-diyl, R′ = 2,6-diisopropylphenyl (2a) and 1-adamantyl (2b)] were synthesized as blue and red crystals by the reactions of isolable dialkylsilylene 3 with 2,6-diisopropylphenyl isocyanide and 1-adamantyl isocyanide. X-ray single-crystal analysis disclosed that molecular structures of 2a and 2b were close to each other and were characterized to be allenic rather than zwitterionic or a silylene-isocyanide complex. The bonding characteristics of silaketenimines are found to be affected strongly by the substituents on silicon and nitrogen atoms. Remarkable red-shift of the π(Si=C) → π*(C=N) band of 2a [λmax/nm (ε) 647(156)] compared with that of 2b [465 nm (109)] is ascribed to lowering of the π*(C=N) orbital level due to significant interaction between π*(C=N) and π*(N-aryl) orbitals.

Original languageEnglish
Pages (from-to)4228-4229
Number of pages2
JournalJournal of the American Chemical Society
Volume128
Issue number13
DOIs
Publication statusPublished - 2006 Apr 5

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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