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Paper | Special issue | Vol 40, No. 2, 1995, pp.757-776
Published online, 1st January, 1970
DOI: 10.3987/COM-94-S64
Bispyridyl- and Bisquinolylmenthanes. NMR-based Charge Mapping of the Carbanions and Metal Ligand Properities

Alessandro Abbotto, Silvia Bradamante, Giorgio A. Pagani, Henry Rzepa, and Federica Stoppa

*Dipartimento di Chimica Organica e Industriale, Centro C. N. R., V. Venezian 19 I-20133 Milano, Italy

Abstract

Nmr evidence is obtained for mixtures of geometrical stereoisomers of carbanions in DMSO solution of bis(4-)- and bis(2-pyridyl)methane (1) and (2), bis(2-pyridyl)acetonitrile (3), and bis(2-quinolyl)methane (4). When incorporated into Π-charge/shift relationships the 13C and 15N nmr data provide access to charge demands cx of the heterocycles, that is the fraction of Π-charge withdrawn by the rings from the carbanionic carbon. Compounds (3) and (4) behave as ligands LH, whose anions L- produce neutral chelates with divalent metal ions (Met = Zn2+, Pd2+). With Met = Co2+, Cu2+, Mn2+ the ligand LH 3 affords the dimer L2.