The two glycoclusters α- and β-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 macrocycles 1 and 2 was performed, a huge difference in their conformational behavior that heavily influences the presentation mode of their saccharidic moieties was found.

Legnani, L., Compostella, F., Sansone, F., Toma, L. (2015). Cone Calix[4]arenes with Orientable Glycosylthioureido Groups at the Upper Rim: An In-Depth Analysis of Their Symmetry Properties. JOURNAL OF ORGANIC CHEMISTRY, 80(15), 7412-7418 [10.1021/acs.joc.5b00878].

Cone Calix[4]arenes with Orientable Glycosylthioureido Groups at the Upper Rim: An In-Depth Analysis of Their Symmetry Properties

LEGNANI, LAURA;
2015

Abstract

The two glycoclusters α- and β-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 macrocycles 1 and 2 was performed, a huge difference in their conformational behavior that heavily influences the presentation mode of their saccharidic moieties was found.
Articolo in rivista - Articolo scientifico
MOLECULAR MODELING; DFT CALCULATIONS; CALIXARENES; GLYCOCLUSTERS
English
7412
7418
7
Legnani, L., Compostella, F., Sansone, F., Toma, L. (2015). Cone Calix[4]arenes with Orientable Glycosylthioureido Groups at the Upper Rim: An In-Depth Analysis of Their Symmetry Properties. JOURNAL OF ORGANIC CHEMISTRY, 80(15), 7412-7418 [10.1021/acs.joc.5b00878].
Legnani, L; Compostella, F; Sansone, F; Toma, L
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/10281/352053
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