Exhibition of the Brønsted acid-base character of a Schiff base in palladium(II) complex formation: lithium complexation, fluxional properties and catalysis of Suzuki reactions in water

Dalton Transactions : an International Journal of Inorganic Chemistry
Rajnish Kumar, Ganesan Mani

Abstract

The reaction of the dialdehyde N,N-di(α-formylpyrrolyl-α-methyl)-N-methylamine with two equiv. of 2,6-diisopropylaniline yielded two Schiff bases: bis(iminopyrrolylmethyl)amine () and its hydrolyzed monoimino compound () after column separation. The dimeric lithium complex [(HL)Li]2 () containing the monoanionic form of was obtained by treating with (n)BuLi. The presence of both proton donors and acceptors causes the diimino compound to undergo tautomerization to exhibit an amine-azafulvene structure, though the central amine nitrogen competes for a proton. As a result, in the presence of Pd(2+) ions, the cationic complex [Pd(Cl)(H2L)][Cl] () containing one pendant amine-azafulvene arm and the protonated central amine nitrogen was obtained. Its X-ray structure showed that the bond distances are reversed for the imino-pyrrole moiety relative to those in the structure of . However, the reaction of with [Pd(OAc)2] afforded the neutral complex [PdL] () containing the dianionic form of the ligand. The reaction of with [PdCl2(PhCN)2] yielded a zwitterionic complex [PdCl2(H2L')] () owing to the presence of the central amine nitrogen. The formation of these palladium complexes with the features mentioned above can be explained by invok...Continue Reading

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Citations

Apr 23, 2016·Sensors·Muhammad Mahtab AlamRaffaele D'Errico
Dec 20, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Ubale Panchsheela AshokDaniel Glossman-Mitnik

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