Characterization of Rh(I) complexes bearing N-2-nitrobenzenesulfonyl substituted, N-heterocyclic carbenes

Tetsuo Sato, Daisuke Yoshioka, Yoichi Hirose, Shuichi Oi

Research output: Contribution to journalArticlepeer-review

3 Citations (Scopus)

Abstract

Synthesis and structural characterization of novel Rh(I) complexes bearing 1,2,4-triazol-3-ylidene or imidazol-2-ylidene substituted with an N-2-nitrobenzenesulfonyl (N-nosyl) group are described. The complexes were characterized by infrared (IR), NMR, and single-crystal X-ray diffraction analyses. The Tolman electronic parameter (TEP) values of both of the 1,2,4-triazol-3-ylidene (2064 cm-1) and imidazol-2-ylidene (2059 cm-1), as determined from the average carbonyl (CO) stretching frequencies for the corresponding RhCl(NHC)(CO)2 (NHC = N-heterocyclic carbene) complexes, were higher than that of RhCl(IMes)(CO) 2 (IMes = 1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene) (2050 cm-1). As the TEP values of the NHCs increased, the 13C NMR signal of the carbenic carbon in the corresponding RhCl(NHC)(cod) (cod = 1,5-cyclooctadiene) and RhCl(NHC)(CO)2 complexes shifted downfield. Moreover, the crystallographic analysis of the RhCl(NHC)(cod) complexes revealed that one of the SO bonds in the sulfonyl group could be conjugated with the NHC frameworks, while the remaining SO bond conjugated with the 2-nitrophenyl groups of the N-nosyl substituent.

Original languageEnglish
Pages (from-to)20-26
Number of pages7
JournalJournal of Organometallic Chemistry
Volume753
DOIs
Publication statusPublished - 2014 Mar 1

Keywords

  • 2-Nitrobenzenesulfonyl group
  • Electronic property
  • N-Heterocyclic carbene
  • Rhodium complex

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry
  • Materials Chemistry

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