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.

Department(s)

Chemistry

Keywords and Phrases

1,3 Propanediamine; 1,4 Dimethylpiperazine; Cadaverine; Dimer; Ethylenediamine; Guanidine Derivative; Hydrogen; Methylamine; N,n,n',n' Tetramethylguanidine; Piperazine Derivative; Putrescine; Squaric Acid; Tetramer; Unclassified Drug; Article; Chemical Analysis; Chemical Structure; Hydrogen Bond; Interactions; Diamines; Hydrogen-bonding; Squaric Acid; Supramolecular Chemistry

International Standard Serial Number (ISSN)

0022-2860

Document Type

Article - Journal

Document Version

Citation

File Type

text

Language(s)

English

Rights

© 2002 Elsevier, All rights reserved.

Publication Date

06 Nov 2002

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