Synthesis and spectral characterization of sparteine and α -isosparteine complexes with copper(II) sulfate

Abstract

Complexes of CuSO 4 of the general formula [Cu(C 15 H 26 N 2 )SO 4 ] where [C 15 H 26 N 2 ] is sparteine or -isosparteine have been obtained from copper(II) and an appropriate alkaloid. The 1 : 1 (metal : alkaloid) stoichiometry was confirmed by elemental analysis. The compounds have been characterized by mass spectrometry, IR, and UV-Vis spectroscopy. The magnetic properties were also determined; no anti-ferromagnetic behavior was observed. Information on the geometry of newly obtained compounds was obtained using quantum-chemical calculations.

Crystal structure of sparteinium tetrachlorocuprate monohydrate-packing polymorph

“…The presence of two amine atoms in the structure of sparteine led to its use as a bidentate ligand in various complexes (e.g., involving copper [1][2][3][4][5][6][7][8][9][10][11][12][13]). Following quaternization of both nitrogen atoms in the molecule sparteine was used as a dication in metalloorganic copper salts [14,15].…”

NMR Spectra of Sparteine N1-oxide and α-Isosparteine N-oxide

“…Naturally occurring (–)-sparteine is an equilibrium mixture in which the conformer possessing a boat ring C and trans junction of rings C/D predominates [ 1 , 2 , 3 , 4 ]. On the other hand, the less stable all-chair conformer participates in complex formation [ 5 , 6 , 7 ]. The compound α-isosparteine, consisting of two trans-quinolizidine systems, exists solely in an all-chair conformation, and similarly in the free base form [ 8 ] and in metal complexes [ 5 , 6 , 7 , 9 , 10 ].…”

“…On the other hand, the less stable all-chair conformer participates in complex formation [ 5 , 6 , 7 ]. The compound α-isosparteine, consisting of two trans-quinolizidine systems, exists solely in an all-chair conformation, and similarly in the free base form [ 8 ] and in metal complexes [ 5 , 6 , 7 , 9 , 10 ]. As a continuation of our study on the complex forming ability of bis-quinolizidine alkaloids [ 6 , 7 , 9 , 10 ], the choice of N-oxides as ligands was made.…”

“…The compound α-isosparteine, consisting of two trans-quinolizidine systems, exists solely in an all-chair conformation, and similarly in the free base form [ 8 ] and in metal complexes [ 5 , 6 , 7 , 9 , 10 ]. As a continuation of our study on the complex forming ability of bis-quinolizidine alkaloids [ 6 , 7 , 9 , 10 ], the choice of N-oxides as ligands was made. We have already obtained the complexes of sparteine N16-oxides with lithium [ 11 ] and zinc [ 12 ] salts.…”