The novel hydrogen bonding motifs and supramolecular patterns in 2,4-diaminopyrimidine-nitrobenzoate complexes

N. Stanley, P. T. Muthiah, S. J. Geib, P. Luger, M. Weber, M. Messerschmidt

Research output: Contribution to journalArticle

38 Scopus citations

Abstract

The crystal structures of the hydrogen-bonded, 1:1 molecular complexes of nitro (ortho, meta and para) benzoic acids with two 2,4-diaminopyrimidine derivatives (trimethoprim and pyrimethamine) have been investigated in detail (1-5). In all the crystal structures except pyrimethamine o-nitrobenzoate (3), the carboxylate group of the respective anions interacts with the protonated trimethoprim or pyrimethamine moiety in a linear fashion through a pair of N-H⋯O hydrogen bonds to form a cyclic hydrogen-bonded motif. This cyclic hydrogen-bonded motif is self-organized in different ways to get the novel types of hydrogen bonding motifs and supramolecular patterns. In the crystal structure of pyrimethamine o-nitrobenzoate (3), the chelating type of hydrogen bonding motif is self-organized to get a helical supramolecular pattern. In the crystal structures of both pyrimethamine m-nitrobezoate (4) and pyrimethamine p-nitrobenzoate (5), a novel type of an alternate arrangement of DADA (D represents donor and A represents acceptor) and DDAA arrays is present, resulting in the formation of hydrogen-bonded ladders.

Original languageEnglish (US)
Pages (from-to)7201-7210
Number of pages10
JournalTetrahedron
Volume61
Issue number30
DOIs
StatePublished - Jul 25 2005
Externally publishedYes

Keywords

  • Aminopyrimidine-carboxylate interactions
  • Crystal engineering
  • Non-covalent interactions
  • Self-organization
  • Supramolecular chemistry

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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