Synthesis, IR Spectra, and Steric Structure of Macrocycles Derived from Pyrimidine Compounds

Authors: Shagidullin, R.R.; Chernova, A.V.; Doroshkina, G.M.; Kataev, V.E.; Bazhanova, Z.G.; Katsyuba, S.A.; Reznik, V.S.; Mikhailov, A.S.; Giniyatullin, R.K.; Pashkurov†, N.G.; Efremov, Y.Y.; Nafikova, A.A.

Source: Russian Journal of General Chemistry, Volume 72, Number 10, October 2002 , pp. 1625-1632(8)

Publisher: MAIK Nauka/Interperiodica

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A new macrocycle including pyrimidine fragments, 12,23,36-trimethyl-24,40-dioxo-15,33-dithia-2,9,13,22,26,35,38,39-octaazatetracy clo[,14.122,26]tetraconta-1(38),10(39),11,13,23,34,36-heptaene, was synthesized. According to the data of IR and UV spectroscopy and HF/6-31G** quantum-chemical calculations, macrocyclic compounds of this series in crystal exist in the amino form, one NH group of which is likely to be involved in intramolecular hydrogen bond, and the other, in intermolacular hydrogen bond. The strength of the latter depends on the macroring size. In solution, the above structures are supplemented by conformers containing both intramolecularly H-bonded and free amino groups, predominantly with trans structure of the HÄNÄCÍN fragment. The imino form of the aminopyrimidine moieties is hardly probable.

Document Type: Research Article

Affiliations: Arbuzov Institute of Organic and Physical Chemistry, Kazan Research Center, Russian Academy of Sciences, Kazan, Tatarstan, Russia

Publication date: October 1, 2002



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