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Stacked aryl groups in P-resolved cyclic phosphonamides as a new conformational constraint

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Abstract

Along the lines of a systematic investigation of conformational constraints promoted by weak interactions, the aryl-stacked structures of some chiral cyclic phosphonamides synthesised with the aid of Betti bases as chirality inducers were investigated by X-ray diffraction analysis and NMR spectroscopy. The synthesised systems showed the stacked conformation between two of their aryl groups, leading to pre-organized structures. The π–π stacking motif between the aromatic rings was observed in solid state and in solution, suggesting that this supramolecular synthon could be used as a conformational constraining tool in the development of drug molecule candidates based on chiral cyclic phosphonamides. The disabling of the π–π stacking motif was pursued by adding an ortho-substituent on one aromatic ring.

Graphical abstract: Stacked aryl groups in P-resolved cyclic phosphonamides as a new conformational constraint

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Publication details

The article was received on 02 Sep 2019, accepted on 23 Oct 2019 and first published on 23 Oct 2019


Article type: Paper
DOI: 10.1039/C9CE01382B
CrystEngComm, 2019, Advance Article

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    Stacked aryl groups in P-resolved cyclic phosphonamides as a new conformational constraint

    M. A. M. Capozzi, C. Pigliacelli, G. Terraneo and C. Cardellicchio, CrystEngComm, 2019, Advance Article , DOI: 10.1039/C9CE01382B

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