Ams. Silva et al., SYNTHESIS AND MOLECULAR-STRUCTURE OF NEW O N/O LIGANDS - BIS-PHENOL-PYRIDINE AND BIS-PHENOL-PYRAZOLE/, Tetrahedron, 53(34), 1997, pp. 11645-11658
Two new heterocyclic ligands, 2,6-bis-(2'-hydroxyphenyl)pyridine 2 and
3,5-bis-(2'-hydroxyphenyl)pyrazole 4 have been prepared. The molecula
r structures of 2,6-bis-(2'-methoxyphenyl)pyridine I, the tetrafluorob
orate salt of 2,6-bis-(2'-hydroxyphenyl)pyridine 3 (a monohydrate) and
that of compound 4 have been determined by X-Ray analysis. In 1, the
phenyl rings me oriented so that the oxygen atoms of the methoxy group
s re placed away front the nitrogen of the pyridine to overcome electr
onic repulsion. In salt 3, intramolecular hydrogen bonds are found bet
ween the pyridinium proton and the hydroxyl atoms which are involved i
n strong O-H ... O and O-H ... F interactions. In addition, the water
molecule participates in a bridging hydrogen bond network with the BF4
-. The molecules in 4, are also held together by hydrogen bonds where
the hydroxyl groups act as both a donor and an acceptor and are respon
sible for the formation of chains. (C) 1997 Elsevier Science Ltd.