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Journal ArticleDOI

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

09 Oct 2007-Journal of Coordination Chemistry (Taylor & Francis Group)-Vol. 60, Iss: 22, pp 2441-2448
TL;DR: In this paper, complexes of CuSO4 of the general formula [Cu(C15H26N2)SO4] where sparteine or α-isosparteine have been obtained from copper(II) and an appropriate alkaloid.
Abstract: Complexes of CuSO4 of the general formula [Cu(C15H26N2)SO4] where [C15H26N2] is sparteine or α-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.
Citations
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Journal ArticleDOI
TL;DR: In this paper, the crystal structures of copper(II) isothiocyanate complexes with two sparteine epimers, (−)-l-sparteine (Sp) and (−)-α-isosparteine(α-Sp), were determined.

11 citations

Journal ArticleDOI
TL;DR: In this paper, a new ZnX 2 (X = Cl, Br) complexes with sparteine N1 -oxide, spartine epi - N16 -oxide and lupanine N -oxide were obtained and characterized by spectroscopic and crystallographic methods.

3 citations

Journal ArticleDOI
TL;DR: Sparteine N1-oxide and α-isosparteine N-oxide were prepared and their structures determined for the first time by 1H- and 13C-NMR spectroscopy using two-dimensional techniques.
Abstract: Sparteine N1-oxide and α-isosparteine N-oxide were prepared and their structures determined for the first time by 1 H- and 13 C-NMR spectroscopy using two-dimensional techniques. The N-oxide effects were also calculated. Keywords: Sparteine, α-isosparteine, N-oxides, NMR spectroscopy, DFT calculations. Introduction The wide use of quinolizidine alkaloids in chemistry is related first of all with a possibility of configurational-conformational changes that could take place in the bis-quinolizidine skeleton. Naturally occurring (–)-sparteine is an equilibrium mixture in which the conformer possessing a boat ring C and trans junction of rings C/D predominates [1-4]. On the other hand, the less stable all-chair conformer participates in complex formation [5-7]. 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 [5-7,9,10]. 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. This time the subject of our study was the synthesis of the complexes of sparteine N1-oxide, sparteine epi-N-oxide and α-isosparteine N-oxide. NMR spectroscopy is known to permit observation of conformational changes taking place in the structure of the ligands during complexation reactions. Moreover, a comparison of the chemical shifts of carbon atoms and protons of the initial alkaloid and the complex formed, enables determination of the effects of complexation. The present work is a continuation of our studies on the structural investigation of bis-quinolizidine alkaloids [13-17]. The NMR data of sparteine N16-oxide and

3 citations


Cites background from "Synthesis and spectral characteriza..."

  • ...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 [5-7,9,10]....

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  • ...On the other hand, the less stable all-chair conformer participates in complex formation [5-7]....

    [...]

  • ...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....

    [...]

Journal ArticleDOI
TL;DR: In this paper, a new polymorph of sparteinium tetrachlorocuprate monohydrate (C15H28N2)CuCl4·H2O] is reported.
Abstract: A new polymorph of sparteinium tetrachlorocuprate monohydrate [(C15H28N2)CuCl4·H2O] is reported. The structure of the analyzed crystal was solved in the orthorhombic P212121 space group with the following unit cell parameters at 295 K: a = 9.7722(2) A; b = 13.4582(3) A; c = 15.1582(3) A. The various types of hydrogen bonding interactions existing in the crystal structure of this salt were compared with the data of the previously reported polymorph. XRPD measurement proved that our salt consists of a pure phase of the new polymorph. Cooling down the salt to ca. 230 K caused its color to change from orange-brown to yellow. DSC experiments revealed that during the cooling an endothermic process takes place corresponding to the mentioned color change of the salt.

1 citations

Journal ArticleDOI
TL;DR: In this article, a tetrahedrally distorted complex of α-isosparteine, β-issparteine and 2-methyl sparteine with FeCl 2 has been synthesized.

1 citations

References
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Book
01 Jan 1983
TL;DR: In this paper, the authors present tables and charts of spectrum-structure correlations for all major spectroscopic techniques (C13 NMR, 1H-NMR, IR, MS, UV/VIS).
Abstract: "This book contains tables and charts of spectrum-structure correlations for all major spectroscopic techniques (C13-NMR, 1H-NMR, IR, MS, UV/VIS). It has been designed for those who are routinely faced with the task of interpreting this type of spectral information. ...

987 citations


"Synthesis and spectral characteriza..." refers background in this paper

  • ...The IR spectra of new compounds exhibit additional bands at 1442 and 1100 cm (1), as expected for (SO(2) 4 ) [26] (figure 3)....

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Journal ArticleDOI
TL;DR: The crystal structures of the two chiral alkyllithium bases [n-BuLi.(-)-sparteine]2 (1) and [Et2O.(i-PrLi)2 (2) have been determined and significantly different Li-C distances are found in the central four-membered ring of compound 2.
Abstract: The crystal structures of the two chiral alkyllithium bases [n-BuLi·(−)-sparteine]2 (1) and [Et2O·(i-PrLi)2·(−)-sparteine] (2) have been determined. For compound 1, a symmetric dimer is observed in the solid state, with two (−)-sparteine ligands coordinating to the lithium centers. Because of steric reasons, compound 2 crystallizes as an unsymmetric dimer with the four methyl groups pointing away from the sterically demanding (−)-sparteine ligand. Compound 2 contains one four-coordinate lithium center [coordinated to (−)-sparteine] and one three-coordinate lithium center (coordinated to Et2O). As a result of this arrangement, significantly different Li−C distances are found in the central four-membered ring of compound 2.

74 citations

Journal ArticleDOI
TL;DR: An attempt has been made to rationalize the nature of the specific interaction of C α H(a) bonds with the lone electron pair on nitrogen in the compounds investigated.

72 citations

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