Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 80, Issue 15, Pages 7412-7418Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.5b00878
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- Italian Ministry of University and Research (Italian network for the development of multivalent nanosystems) [2010JMAZML]
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The two glycodusters alpha- and beta-D-mannosylthioureidocalix[4]arenes 1 and 2 in the cone geometry have been submitted to a conformational investigation with the DFT approach at the standard B3LYP/6-31G(d) level and using a water continuum solvent model. After a reasoned choice of the level of calculation and the evaluation of the properties of the monomeric components of 1 and 2, the intrinsic conformational properties of cone calix[4]arenes with orientable groups at the upper rim were thoroughly analyzed. From the possible combinations of the directions that the groups may assume, 10 different geometries derive, all chiral. These geometries are interchangeable through two different processes, named breathing equilibrium and arrow rotation, that allow a dense network connection among them. When the modeling of whole macrocydes 1 and 2 was performed, a huge difference in their conformational behavior that heavily influences the presentation mode of their saccharidic moieties was found.
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