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Building Functionality into 4′‐Hydrazone Derivatives of 2,2′: 6′,2″‐Terpyridine
Author(s) -
Beves Jonathon E.,
Constable Edwin C.,
Housecroft Catherine E.,
Neuburger Markus,
Schaffner Silvia,
Zampese Jennifer A.
Publication year - 2009
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200900132
Subject(s) - chemistry , terpyridine , hydrazone , protonation , substituent , amine gas treating , stereochemistry , medicinal chemistry , combinatorial chemistry , metal , organic chemistry , ion
The syntheses of the five 2,2′: 6′,2″‐terpyridine (tpy) ligands 5 – 9 functionalized in the 4′‐position with a hydrazone substituent RR′CNNH (R=R′=Me; R=H, R′=4‐BrC 6 H 4 , 4‐O 2 NC 6 H 4 , 4‐MeOC 6 H 4 , or 3,5‐(MeO) 2 C 6 H 3 ) are described. Protonation of the tpy domain of the ligands is facile. Solution behaviour has been studied by NMR and electronic spectroscopies. Representative structural data are presented for neutral and monoprotonated ligands, and illustrate that H‐bonding involving the formal amine NH unit is a dominant structural motif in all cases.