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Pubmed ID :28825793
Publication Date : //

Ruthenium-Hydride Mediated Unsymmetrical Cleavage of Benzofuroxan to 2-Nitroanilido with Varying Coordination Mode.


The reaction of R-benzofuroxan (R = H, Me, Cl) with the metal precursor [Ru(Cl)(H)(CO)(PPh)] (A) or [Ru(Cl)(H)(CHCN)(CO)(PPh)] (B) in CHCN at 298 K resulted in the intermediate complex [Ru(Cl)(L)(CHCN)(CO)(PPh)] (L = monodentate 2-nitroanilido) (1, pink), which however underwent slow transformation to the final product [Ru(Cl)(L)(CO)(PPh)] (L = bidentate 2-nitroanilido) (2, green). On the contrary, the same reaction in refluxing CHCN directly yielded 2 without any tractable intermediate 1. Structural characterization of the intermediates 1a-1c and the corresponding final products 2a-2c (R = H, Me, Cl) authenticated their identities, revealing ruthenium-hydride mediated unsymmetrical cleavage of benzofuroxan to hydrogen bonded monodentate 2-nitroanilido (L) in the former and bidentate 2-nitroanilido (L) in the latter. The spectrophotometric monitoring of the transformations of B → 1 as well as 1 → 2 with time and temperature established the first order rate process with associatively activated pathway for both cases. Both 1 and 2 exhibited one reversible oxidation and an irreversible reduction within ±1.5 V versus saturated calomel reference electrode in CHCN with slight variation in potential based on substituents in the benzofuroxan framework (R = H, Me, Cl). Spectroscopic (electron paramagnetic resonance and UV-vis) and density functional theory calculations collectively suggested varying contribution of metal based orbitals along with the ligand in the singly occupied molecular orbital of 1 or 2, ascertaining the noninnocent potential of the in situ generated (L) or (L).

Authors : Ghosh Prabir , Panda Sanjib , Banerjee Soumyodip , Lahiri Goutam Kumar ,

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