Russo Marco, Lo Meo Paolo
Dipartimento di Scienze e Tecnologie Biologiche, Chimiche e Farmaceutiche (STEBICEF), University of Palermo, V.le delle Scienze ed. 17, 90128 Palermo, Italy.
ATeNCenter, University of Palermo, V.le delle Scienze ed. 18, 90128 Palermo, Italy.
Beilstein J Org Chem. 2017 Dec 15;13:2698-2709. doi: 10.3762/bjoc.13.268. eCollection 2017.
Polarimetry was used to investigate the binding abilities of a chiral calix[4]resorcinarene derivative, bearing L-proline subunits, towards a set of suitably selected organic guests. The simultaneous formation of 1:1 and 2:1 host-guest inclusion complexes was observed in several cases, depending on both the charge status of the host and the structure of the guest. Thus, the use of the polarimetric method was thoroughly revisited, in order to keep into account the occurrence of multiple equilibria. Our data indicate that the stability of the host-guest complexes is affected by an interplay between Coulomb interactions, π-π interactions, desolvation effects and entropy-unfavorable conformational dynamic restraints. Polarimetry is confirmed as a very useful and versatile tool for the investigation of supramolecular interactions with chiral hosts, even in complex systems involving multiple equilibria.
使用旋光测定法研究了带有L-脯氨酸亚基的手性杯[4]间苯二酚芳烃衍生物与一组经过适当选择的有机客体的结合能力。在几种情况下，观察到同时形成了1:1和2:1的主客体包合配合物，这取决于主体的电荷状态和客体的结构。因此，对旋光测定法的使用进行了全面回顾，以便考虑到多重平衡的存在。我们的数据表明，主客体配合物的稳定性受到库仑相互作用、π-π相互作用、去溶剂化效应和熵不利的构象动态限制之间相互作用的影响。旋光测定法被确认为研究与手性主体的超分子相互作用的一种非常有用且通用的工具，即使在涉及多重平衡的复杂系统中也是如此。
