Symmetrically 4,6-disubstituted 2-aminopyrimidines and 2-amino-5-nitrosopyrimidines: interplay of molecular, molecular-electronic and supramolecular structures

A Quesada, A Marchal, M Melguizo, J N Low, C Glidewell

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29 Citations (Scopus)

Abstract

The structures of six symmetrically 4,6-disubstituted 2-aminopyrimidines, four of them containing a 5-nitroso substituent, have been determined. The nitroso compounds, in particular, exhibit polarized molecular-electronic structures leading to extensive charge-assisted hydrogen bonding. The intermolecular interactions observed include hard hydrogen bonds of N-H...N and N-H...O types together with O-H...O and O-H...N types in 2-amino-4,6-bis(2-hydroxyethylamino)-5-nitrosopyrimidine; soft hydrogen bonds of the C-H...O type in both 2-amino-4,6-bis(morpholino)-5-nitrosopyrimidine (3) and 2-amino-4,6-bis(benzylamino)-5-nitrosopyrimidine (4), and of the C-H...pi(arene) type in both 2-amino-4,6-bis( piperidino) pyrimidine (1) and 2-amino-5-nitroso-4,6-bis(3-pyridylmethoxy) pyrimidine (5); and aromatic pi...pi stacking interactions in 2-amino-5-nitroso-4,6-bis( 3-pyridylmethoxy) pyrimidine. The supramolecular structures formed by the hard hydrogen bonds are finite, zero-dimensional in (1), one-dimensional in 2-amino-4,6-bis( 3-pyridylmethoxy) pyrimidine (2), two-dimensional in both (3) and (4), and three-dimensional in both (5) and 2-amino-4,6-bis(2-hydroxyethylamino)-5-nitrosopyrimidine.

Original languageEnglish
Pages (from-to)76-89
Number of pages14
JournalActa Crystallographica. Section B, Structural Science
Volume60
Issue number1
DOIs
Publication statusPublished - Feb 2004

Keywords

  • CRYSTAL-STRUCTURE PREDICTION
  • SMALL ORGANIC-MOLECULES
  • X-RAY-DIFFRACTION
  • HYDROGEN-BONDS
  • RING
  • CHAINS
  • REFINEMENT
  • 3-CENTER

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