Adam, Kenneth R., Atkinson, Ian M., Lindoy, Leonard F., McCool, Brian J., and Rambusch, Torsten (2003) Self-assembly directed by NH-O hydrogen bonding: new molecular assemblies derived from N,N-tetramethyl-1,2-diaminoethane and malonic or fumaric acid incorporating "proton transfered" hydrogen bonds. Journal of supramolecular chemistry, 1 (4-6). pp. 201-205.

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Abstract

Co-crystn. of N,N-tetramethyl-1,2-diaminoethane (TMEN) and malonic or fumaric acid from water in a 1:1 ratio results in cryst. products whose X-ray structures show that they contain hydrogen-bonded motifs in self-assembled arrays. The stoichiometry of the malonate-contg. assembly is 1:2, [TMENH2(hydrogen malonate)2], while that of the fumarate-contg. assembly is 1:1:1 (TMENH2, fumarate, fumaric acid). In each structure, protons from individual carboxylic acids have been transferred onto the nitrogens of N,N-tetramethyl-1,2-diaminoethane (TMEN) to yield diammonium cations; the ammonium protons hydrogen bond to carboxylate oxygens of hydrogen malonate in one case or to fumarate anions in the other. The hydrogen malonate-contg. structure has layers of aligned diprotonated TMEN sepd. by layers of hydrogen malonate anions. Successive hydrogen malonate ions are hydrogen bound in an "alternate" manner between adjacent protonated TMEN layers. Each [TMENH2(hydrogen malonate)2] moiety describes an approx. "Z" configuration which are in turn stacked at an oblique angle; adjacent "columns of Zs" are partially interlaced to form the overall array. The fumarate-contg. structure consists of parallel ribbons of alternating, hydrogen bonded, fumarate dianions and fumaric acid mols. These form layers alternating with layers of diammonium ions which lie essentially in the xy plane. The diammonium ions form parallel staggered head-to-tail chains along the y axis and so run at an angle across the fumarate-fumaric acid ribbons.

Item ID:	573
Item Type:	Article (Research - C1)
ISSN:	1472-7862
Keywords:	Hydrogen bond (N×××H-O; crystallog. study on product from co-crystn. of N,N-tetramethyl-1,2-diaminoethane and malonic and fumaric acid, resp., from water) Crystal structure Molecular structure Self-assembly Supramolecular structure (crystallog. study on product from co-crystn. of N,N-tetramethyl-1,2-diaminoethane and malonic and fumaric acid, resp., from water) Molecular structure (optimized; crystallog. study on product from co-crystn. of N,N-tetramethyl-1,2-diaminoethane and malonic and fumaric acid, resp., from water)
Additional Information:	Copyright 2003 Elsevier. Title discontinued as at 2003
Date Deposited:	09 Oct 2006
FoR Codes:	03 CHEMICAL SCIENCES > 0303 Macromolecular and Materials Chemistry > 030302 Nanochemistry and Supramolecular Chemistry @ 100%
SEO Codes:	97 EXPANDING KNOWLEDGE > 970103 Expanding Knowledge in the Chemical Sciences @ 100%
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