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Isocyanoazulenes (CNAz) constitute a relatively new class of isocyanoarenes that offers rich structural and electronic diversification of the organic isocyanide ligand platform. This article considers a series of 2-isocyano-1,3-X 2 -azulene ligands (X = H, Me, CO 2 Et, Br, and CN) and the corresponding zero-valent complexes thereof, [(OC) 5 Cr(2-isocyano-1,3-X 2 -azulene)]. Air- and thermally stable, X-ray structurally characterized 2-isocyano-1,3-dimethylazulene may be viewed as a non-benzenoid aromatic congener of 2,6-dimethyphenyl isocyanide (2,6-xylyl isocyanide), a longtime "workhorse" aryl isocyanide ligand in coordination chemistry. Single crystal X-ray crystallographic {Cr-CNAz bond distances}, cyclic voltametric { E 1/2  (Cr 0/1+ )}, 13 C NMR {δ( 13 CN), δ( 13 CO)}, UV-vis {dπ(Cr) → pπ*(CNAz) Metal-to-Ligand Charge Transfer}, and FTIR {ν N  ≡  C , ν C  ≡  O , k C  ≡  O } analyses of the [(OC) 5 Cr(2-isocyano-1,3-X 2 -azulene)] complexes provided a multifaceted, quantitative assessment of the π-acceptor/σ-donor characteristics of the above five 2-isocyanoazulenes. In particular, the following inverse linear relationships were documented: δ( 13 CO trans ) vs. δ( 13 CN), δ( 13 CO cis ) vs. δ( 13 CN), and δ( 13 CO trans ) vs. k C  ≡  O,trans force constant. Remarkably, the net electron withdrawing capability of the 2-isocyano-1,3-dicyanoazulene ligand rivals those of perfluorinated isocyanides CNC 6 F 5 and CNC 2 F 3 .

molecules/molecules online/molecules annual

Tuning π-Acceptor/σ-Donor Ratio of the 2-Isocyanoazulene Ligand: Non-Fluorinated Rival of Pentafluorophenyl Isocyanide and Trifluorovinyl Isocyanide Discovered