1,8-bis(2-hydroxy-3,5-di-tert-butylbenzyl)-4,11-2 dibenzyl-1,4,8,11-tetraazacyclotetradecane

A Aranburu Leiva, Mandeep Kaur, Sophie Benjamin, Alan M Jones, Stuart Langley, Ryan Mewis

Research output: Contribution to journalArticlepeer-review

2 Citations (Scopus)
168 Downloads (Pure)

Abstract

A cyclam (1,4,8,11-tetraazacyclotetradecane)-based macrocycle bearing two benzyl and two 2-hydroxy-3,5-di-tert-butylbenzyl pendent arms was synthesized and characterized using spectroscopic techniques and single crystal X-ray diffraction. The macrocycle crystallizes in the triclinic space group P-1, with the asymmetric unit containing one-half of the molecule. The structure is stabilized by hydrogen-bonding which exists between the phenolic protons and the nitrogen atoms of the macrocyclic ring. The presence of this hydrogen bonding is observed in the 1H-NMR due to the deshielded nature of the phenolic OH peak (δ 9.99). Cyclic voltammetry of the ligand revealed a single quasi-reversible peak at −0.58 V (Epc = −0.48 V and Epa = −0.68 V), which is due to the electrochemical oxidation of the phenol to the phenoxyl radical.
Original languageEnglish
Article numberM963
JournalMolBank
Volume2017
Issue number4
Early online date13 Oct 2017
DOIs
Publication statusE-pub ahead of print - 13 Oct 2017

Keywords

  • Cyclam
  • Cyclic voltammetry
  • Hydrogen-bonding
  • Macrocycle
  • X-ray diffraction

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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