Inclusion complexes of selected amines with pillar[5]arenes: experimental and molecular dynamics study

Hamad H. Al Mamari*, Iman Al Harrasi, Khulood Al Hadhrami, Yousuf Al Lawati, Fakhreldin O. Suliman

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

2 Citations (Scopus)

Abstract

Selected amines were allowed to form inclusion complexes with selected synthesized pillar[5]arenes. Formation of inclusion complexes were confirmed by MALDI–TOF, ESI–MS analyses and 1H NMR spectroscopy. The complexation was supported by molecular dynamics calculations. Various pillar[5]arenes have been synthesized by BF3·OEt2 (Lewis acid) catalyzed cyclization of 1,4-disubstitutedbenzenes with paraformaldehyde. Selected synthesized host macrocycles; DMpillar[5]arene (7), DPpillar[5]arene (8a), DPGpillar[5]arene (8b) were allowed to form inclusion complexes with N-containing guests; hexamethylenediamine (GA), di-n-octyl amine (GB) and diethyl amine (GC). Host–guest complex formation of the selected pillar[5]arenes with the N-containing guests has been confirmed by MALDI–TOF, ESI–MS analyses and 1H NMR spectroscopy. ESI–MS revealed highly intense ion peaks that correspond to [pillar[5]arene@GA+Na]+ for inclusion complexes of pillar[5]arenes with hexamethylenediamine (GA). ESI–MS confirmed formation of inclusion complexes between pillar[5]arenes with di-n-octyl amine (GB) and diethyl amine (GC) as evidenced by intense peaks that corresponds to [pillar[5]arene@GB+H]+ and [pillar[5]arene@GC+H]+, respectively. Performed molecular dynamics (MD) simulations provided supportive results that indicate the formation of stable complexes between the three pillar[5]arene hosts and the guests included in this study. Hydrogen bonding and CH–π interactions were found amongst the factors that contribute significantly to the stability of these complexes.

Original languageEnglish
Pages (from-to)297-306
Number of pages10
JournalJournal of Inclusion Phenomena and Macrocyclic Chemistry
Volume96
Issue number3-4
DOIs
Publication statusPublished - Apr 1 2020
Externally publishedYes

Keywords

  • Host–guest chemsitry
  • Inclusion complexes
  • Macrocycles
  • Pillar[5]arenes

ASJC Scopus subject areas

  • Food Science
  • Chemistry(all)
  • Condensed Matter Physics

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