Synthesis and structure of stable base-free dialkylsilanimines

Takeaki Iwamoto, Nobuyoshi Ohnishi, Zhenyu Gui, Shintaro Ishida, Hiroyuki Isobe, Satoshi Maeda, Koichi Ohno, Mitsuo Kira

Research output: Contribution to journalArticlepeer-review

46 Citations (Scopus)


Four isolable dialkylsilanimines RH2SiNR (R = CH 2Ph (5a), Ph (5b), 1-adamantyl (5c) and SiMe3 (5d), where RH2 = 1,1,4,4-tetrakis(trimethylsilyl)butane-1,4-diyl) were synthesized as air-sensitive crystals by the reaction of isolable dialkylsilylene 4 with the corresponding azides. X-ray analysis shows that 5a-5d are base-free silanimines and 5a and 5b have a remarkable bent SiN-R structure, while 5c and 5d have an almost linear structure. Distinct π(SiN) →π*(SiN) and n(N)→π*(SiN) transition bands of silicon-nitrogen double bonds were observed for 5a-5d in hexane. A mechanism for the formation of silanimine from the reaction of silylene and azide is discussed using theoretical calculations with the GRRM method for model reactions.

Original languageEnglish
Pages (from-to)1637-1645
Number of pages9
JournalNew Journal of Chemistry
Issue number8
Publication statusPublished - 2010 Aug

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Materials Chemistry


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