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Synthesis and Aggregation Properties of Two‐ and Three‐Armed Nitrogen‐Rich Chelate Ligands: Novel Bis( N ‐acylamidines), Tris( N ‐acylamidines) and Bis(triazapentadienes) with Flexible or Rigid Spacers
Author(s) -
Clodt Juliana Isabel,
Wigbers Christof,
Reiermann Ralph,
Fröhlich Roland,
Würthwein ErnstUlrich
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201100218
Subject(s) - chemistry , deprotonation , ligand (biochemistry) , tris , intermolecular force , tripodal ligand , polymer chemistry , chelation , medicinal chemistry , dicarboxylic acid , hydrogen bond , nitrogen , stereochemistry , organic chemistry , molecule , ion , biochemistry , receptor
Two‐ and three‐armed ligands, like bis( N ‐acylamidines) 7 and 9 , tris( N ‐acylamidines) 8 and bis(1,3,5‐triazapenta‐1,3‐dienes) 10 with different spacers between the ligand moieties, have been easily prepared in moderate‐to‐good yields starting from diamines, triamines or dicarboxylic acid derivatives. Thus, the reaction of diamines and triamines with N ‐acylimidates 3 led to bis( N ‐acylamidines) 7 and tris( N ‐acylamidines) 8 , respectively, linked through the amino group. Ligands 9 , interconnected through the carbonyl groups, were obtained starting from dicarboxylic acid dichlorides and amidines. Bis(triazapentadienes) 10 , linked through carbon atoms, were synthesized from a diamide, which was converted into a bis( N ‐imidoylimidate) 17 followed by reactions with deprotonated amines. These compounds show variable aggregation behaviour in the solid state as a result of intra‐ and intermolecular hydrogen bonding. All compounds were thoroughly characterized including by X‐ray diffraction.