Chiral Tetraamines Based on (S)‐2‐(Aminomethyl)pyrrolidine

Template synthesis and properties of copper(II) complexes

Paul V. Bernhardt, Peter Comba, Trevor W. Hambley, Lisandra L. Martin, K. Várnagy, Luc Zipper

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

The template reaction of {bis[(S)‐2‐(aminomethyl)pyrrolidine]}copper(II) with formaldehyde, nitroethane, and base in MeOH yields optically pure {1,7‐bis[(S)‐pyrrolidin‐2‐yl]‐4‐methyl‐4‐nitro‐2,6‐diazaheptane}‐ copper(II) ([Cu((S,S)‐mnppm)]2+) in high yield. The same reaction with rac‐2‐(aminomethyl)pyrrolidine is also described. Preparative details and spectroscopic and electrochemical properties of the CuII complexes and of the free ligands are reported and compared with structural, spectroscopic and electrochemical data of the CuII complex of the unsubstituted parent ligand 1,7‐bis[(S)‐pyrrolidin‐2‐yl]‐2,6‐diazaheptane (ppm). The crystal structure of [Cu(ppm)]Cl ClO4 has been determined by X‐ray diffraction methods.

Original languageEnglish
Pages (from-to)145-152
Number of pages8
JournalHelvetica Chimica Acta
Volume75
Issue number1
DOIs
Publication statusPublished - 1992

Fingerprint

Copper
templates
Ligands
copper
ligands
synthesis
formaldehyde
Electrochemical properties
Formaldehyde
X-Ray Diffraction
Diffraction
Crystal structure
crystal structure
diffraction
pyrrolidine
nitroethane
perchlorate

ASJC Scopus subject areas

  • Catalysis
  • Biochemistry
  • Drug Discovery
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

Cite this

Chiral Tetraamines Based on (S)‐2‐(Aminomethyl)pyrrolidine : Template synthesis and properties of copper(II) complexes. / Bernhardt, Paul V.; Comba, Peter; Hambley, Trevor W.; Martin, Lisandra L.; Várnagy, K.; Zipper, Luc.

In: Helvetica Chimica Acta, Vol. 75, No. 1, 1992, p. 145-152.

Research output: Contribution to journalArticle

Bernhardt, Paul V. ; Comba, Peter ; Hambley, Trevor W. ; Martin, Lisandra L. ; Várnagy, K. ; Zipper, Luc. / Chiral Tetraamines Based on (S)‐2‐(Aminomethyl)pyrrolidine : Template synthesis and properties of copper(II) complexes. In: Helvetica Chimica Acta. 1992 ; Vol. 75, No. 1. pp. 145-152.
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