Abstract
Analysis of the PMR spectra of cycleanine in CDCl3 (INDOR and double-resonance spectra) measured at various temperatures has shown that the cycleanine molecule exists in a stable symmetrical boat-like conformation for the macrocycle in which the tetrahydroisoquinoline rings acquire a distorted boat form, the benzyl groups are oriented axially, and the distance between them is the greatest. A comparison of the spectra of the cycleanine and its methiodide in CF3COOH (double-resonance spectra) has shown that in solutions of cycleanine in the salt form there are molecules with axial and equatorial methyl groups at the nitrogen atoms (1:1). It has been shown with the aid of paramagnetic reagents that the main associating center in the cycleanine molecule is formed by the methoxy groups in position 7 and 7′, which possess an increased electron density on their oxygen atoms because of their departure from the plane of conjugation with the aromatic ring of the isoquinoline nucleus.
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