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Symmetrical diamides based on 2,6‐bis(methoxycarbonyl)pyridine: Syntheses and metal ion binding studies
Author(s) -
Napitupulu Mery,
Griggs Brendan L.,
Luo ShiXia,
Turner Peter,
Maeder Marcel,
Lawrance Geoffrey A.
Publication year - 2009
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.72
Subject(s) - chemistry , pyridine , denticity , amide , molecule , stereochemistry , metal , medicinal chemistry , crystallography , crystal structure , organic chemistry
ymmetrically‐armed molecules based on a 2,6‐diamidopyridine core, 2,6‐bis[ N ‐(1′‐piperidinylethyl)carbamyl]pyridine ( 1 ), 2,6‐bis[ N ‐(1′‐piperazinylethyl)carbamyl]pyridine ( 2 ), 2,6‐bis[ N ‐2′‐(5′′‐nitropyridine)‐1′‐azapropyl)carbamyl]pyridine ( 3 ), 2,6‐bis[ N ‐(3′‐hydroxypropyl)carbamyl]pyridine ( 4 ), 2,6‐bis[ N ‐(5′‐hydroxy‐3′‐azapentyl)carbamyl]pyridine ( 5 ), 2,6‐bis[ N ‐2′‐oxo‐2′,3′‐dihydropyrimidin‐4′‐yl)carbamyl]‐pyridine ( 6 ) as well as the thioamide analogue 2,6‐bis[(S‐2′‐pyridinyl)carbothiyl]pyridine ( 7 ) have been prepared and characterized. An X‐ray crystal structure of 1 confirms its formation. These molecules are potentially multidentate ligands for metal ions, and complexation has been probed through spectroscopic characterization, particularly by electrospray ionization mass spectrometry, and isolation of some first‐row transition metal complexes. The ligands, with potentially coordinating arms extending from each amide, dominantly form simple 1:1 M:L complexes. They show no tendency toward polynuclear helicate formation. J. Heterocyclic Chem., 46 , 243 (2009).