Legnani, Laura Compostella, Federica Sansone, Francesco Toma, Lucio <i>Cone</i> Calix[4]arenes with Orientable Glycosylthioureido Groups at the Upper Rim: An In-Depth Analysis of Their Symmetry Properties The two glycoclusters α- and β-d-mannosylthioureidocalix­[4]­arenes <b>1</b> and <b>2</b> in the <i>cone</i> 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 <b>1</b> and <b>2</b>, the intrinsic conformational properties of <i>cone</i> 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 macrocycles <b>1</b> and <b>2</b> was performed, a huge difference in their conformational behavior that heavily influences the presentation mode of their saccharidic moieties was found. monomeric components;geometrie;Upper Rim;network connection;DFT approach;Symmetry PropertiesThe;water continuum;orientable groups;arrow rotation;saccharidic moieties;macrocycles 1;presentation mode;B 3LYP level;Orientable Glycosylthioureido Groups;breathing equilibrium;cone geometry 2015-08-07
    https://acs.figshare.com/articles/journal_contribution/_i_Cone_i_Calix_4_arenes_with_Orientable_Glycosylthioureido_Groups_at_the_Upper_Rim_An_In_Depth_Analysis_of_Their_Symmetry_Properties/2142751
10.1021/acs.joc.5b00878.s001