Trianglamines--readily prepared, conformationally flexible inclusion-forming chiral hexamines |
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Authors: | Gawronski Jacek Gawronska Krystyna Grajewski Jakub Kwit Marcin Plutecka Agnieszka Rychlewska Urszula |
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Affiliation: | Department of Chemistry, A. Mickiewicz University, Grunwaldzka 6, 60780 Poznan, Poland. gawronsk@amu.edu.pl |
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Abstract: | Trianglamines, macrocyclic heteraphanes, were readily synthesised through a [3+3] cyclocondensation of (R,R)-1,2-diaminocyclohexane with terephthalaldehyde, followed by NaBH4 reduction and N-alkylation. The macrocyclic ring shows a remarkable ability to change its conformation, as a consequence of rotation about the C-N bonds or nitrogen inversion due to protonation or N-alkylation, as revealed by circular dichroism spectra, computational modelling and X-ray diffraction analysis. The flexible natures of the trianglamine macrocycles allow ready accommodation of a variety of guest molecules to form crystalline inclusion complexes of highly diversified interpenetrating structures. |
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Keywords: | amines circular dichroism conformation analysis macrocycles X‐ray diffraction |
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