Correlation between the stereochemistry of quinolizidine alkaloids and their infrared spectra from 2840-2600 CM−1

Skolik, Jerzy; Krueger, P. J.; Wiewiórowski, M.

doi:10.1016/s0040-4020(01)96339-2

Cited by 82 publications

(8 citation statements)

References 23 publications

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“…Dans le cas de la lupanine, les spectres RMN et IR (Wiewiorowski, Edwards & Bratek-Wiewiorowska, 1967;Skolik, Krueger & Wiewiorowski, 1968) ont montr~ que le cycle C adoptait en solution la conformation bateau. Afin de confirmer ce r6sultat et d'~tab-lir la st6r6ochimie precise de ce compos6, nous avons entrepris la d6termination de la structure cristalline de la ( + )-lupanine.…”

Section: Introductionunclassified

Structure cristalline de la (±)-lupanine

Doucerain¹,

Chiaroni²,

Riche³

1976

Acta Crystallogr Sect B

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Section: Introductionunclassified

Structure cristalline de la (±)-lupanine

Doucerain¹,

Chiaroni²,

Riche³

1976

Acta Crystallogr Sect B

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“…In the range 2840-2600 cm À1 in the spectrum of -isosparteine there are three peaks at 2793, 2758 and 2735 cm À1 . The trans-band of sparteine reveals two absorption maxima at about 2795 and 2760 cm À1 [25]. The attachment of copper atom to N results in the disappearance of the trans-band.…”

Section: Spectroscopic Studiesmentioning

confidence: 99%

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

Jasiewicz

Boczoń

Kowałczyk

2007

Journal of Coordination Chemistry

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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.

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“…Strong signals in the range of 2800–2700 cm −1 , the so-called Bohlmann bands [ 71 ], named after their discoverer, are observed in response to the presence of a substituent of the amine nitrogen atom, in the form of a sp 2 carbon atom (which is a ring member) or sp 3 . Originally, the study of these bands was used to clarify the stereochemistry of alkaloids, especially those containing the quinolizidine system [ 72 , 73 ]—found in the Egyptian water lily, called the tiger lotus, in the Scotch broom ( Cytisus , Fabaceae) or in the Andean lupin ( Lupinus , Fabaceae), such as lupinine or sparteine and its oxo-derivatives. In order to clearly illustrate the core of the Bohlmann effect, the commonly known anomeric effect should be recalled.…”

Section: Hydrazidesmentioning

confidence: 99%

Different Schiff Bases—Structure, Importance and Classification

et al. 2022

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Schiff bases are a vast group of compounds characterized by the presence of a double bond linking carbon and nitrogen atoms, the versatility of which is generated in the many ways to combine a variety of alkyl or aryl substituents. Compounds of this type are both found in nature and synthesized in the laboratory. For years, Schiff bases have been greatly inspiring to many chemists and biochemists. In this article, we attempt to present a new take on this group of compounds, underlining of the importance of various types of Schiff bases. Among the different types of compounds that can be classified as Schiff bases, we chose hydrazides, dihydrazides, hydrazones and mixed derivatives such as hydrazide–hydrazones. For these compounds, we presented the elements of their structure that allow them to be classified as Schiff bases. While hydrazones are typical examples of Schiff bases, including hydrazides among them may be surprising for some. In their case, this is possible due to the amide-iminol tautomerism. The carbon–nitrogen double bond present in the iminol tautomer is a typical element found in Schiff bases. In addition to the characteristics of the structure of these selected derivatives, and sometimes their classification, we presented selected literature items which, in our opinion, represent their importance in various fields well.

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Correlation between the stereochemistry of quinolizidine alkaloids and their infrared spectra from 2840-2600 CM−1

Cited by 82 publications

References 23 publications

Structure cristalline de la (±)-lupanine

Structure cristalline de la (±)-lupanine

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

Different Schiff Bases—Structure, Importance and Classification

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