Supramolecular hydrogen-bonded structures in organic amine squarates

Abstract

Structures of monohydrogen squarates of methylamine, ethylenediamine, 1,3-diaminopropane, 1,4-diaminobutane, 1,5-diaminopentane, N,N'-diemethylpiperazine and N,N,N',N'-tetramethylguanidine have been studied in detail. The supramolecular hydrogen-bonded molecular networks are formed by the monoanion of squaric acid by itself or in association with the parent acid. Three types of hydrogen-bonded motifs are observed in these compounds, namely a liner chain, a cyclic dimer and a cyclic tetramer. These hydrogen-bonded motifs formed by the squaric acid species interact with the amine through N-H···O hydrogen-bonding and give rise to predominantly layered structures, while some of them also exhibit three-dimensional structures. Two of the monohydrogen squarate structures also exhibit π-π interactions between two squarate rings. The various hydrogen-bonding parameters in the amine squarates are discussed at length.