Ferrocene-1,1'-dicarboxylic acid as a bulding block in supramolecular chemisry: supramolecular structures in one, two, and three-dimensions

CM Zakaria, G Ferguson, AJ Lough, Christopher Glidewell

Research output: Contribution to journalArticlepeer-review

37 Citations (Scopus)

Abstract

The supramolecular structures have been determined for nine adducts formed between organic diamines and ferrocene-1,1'-dicarboxylic acid. In the salt-like 1:1 adduct (1) formed with methylamine, the supramolecular structure is one-dimensional, whereas in the 1:1 adducts formed with 1,4-diazabicyclo[2.2.2]octane, (2), and 4,4'-bipyridyl, (4), and in the hydrated 2:1 adduct (3) formed with morpholine, the hard hydrogen bonds form one-dimensional structures, which are expanded to two dimensions by soft C-H...O hydrogen bonds. The hard hydrogen bonds generate two-dimensional structures in the 2:1 adduct (5) formed with octylamine, where the ferrocene component lies across a centre of inversion, in the 1:1 adduct (6) formed with piperidine and in the tetrahydrofuran-solvated 1:1 adduct (7) formed with di(cyclohexyl)amine. In the 2:3 adduct (8) formed by tris-(2-aminoethyl)amine, and in the 2:1 adduct (9) formed with 2-(4' -hydroxyphenyl)ethylamine (tyramine), where Z' = 1.5 in space group P (1) over bar 1, the hard hydrogen bonds generate three-dimensional structures. No H transfer from O to N occurs in (4) and only partial transfer of H occurs in (2); in (1), (6) and (7), one H is transferred to N from each acid molecule, and in (3), (5), (8) and (9), two H are transferred from each acid molecule.

Original languageEnglish
Pages (from-to)786-802
Number of pages17
JournalActa Crystallographica. Section B, Structural Science
VolumeB58
DOIs
Publication statusPublished - Oct 2002

Keywords

  • HYDROGEN-BONDED ADDUCTS
  • X-RAY-DIFFRACTION
  • MOLECULAR-STRUCTURES
  • 1/1 ADDUCTS
  • CRYSTAL
  • FERROCENE-1,1'-DIYLBIS(DIPHENYLMETHANOL)
  • 4,4'-BIPYRIDYL
  • PIPERAZINE
  • 298-K

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