Tetrahedron ( IF 2.1 ) Pub Date : 2018-02-24 , DOI: 10.1016/j.tet.2018.01.049 Quoc-Thiet Nguyen , Suban K. Sahoo , Heung-Jin Choi
The stability of the vase-like conformation of a deep cavitand 1 with four imidazoquinoxaline flaps was studied in CDCl3/CD3OD by 1H NMR method. The annular tautomerism of cavitand 1·4MeOD in CDCl3/CD3OD (1:9 v/v) was investigated by 1H NMR and the free energy of activation (ΔG‡268) of this process was measured as 12.9 kcal/mol at a coalescence temperature of 263 K. The inclusion complexation of 1 with various rod-like fatty amides and fatty esters resulted the formation of host-guest complexes in 1:1 stoichiometry where the alkyl chain of guests are coiled within the cavity and stabilized by CH/π interactions with the enlarged aromatic π surfaces of imidazoquinoxaline flaps.
中文翻译:
深空洞与咪唑并喹喔啉瓣的夹杂物络合形成稳定的花瓶状构象
通过1 H NMR方法在CDCl 3 / CD 3 OD中研究了具有四个咪唑并喹喔啉瓣的深腔体1的花瓶状构象的稳定性。通过1 H NMR研究了Cavitand 1 ·4MeOD在CDCl 3 / CD 3 OD(1:9 v / v)中的环状互变异构现象,该过程的活化自由能(ΔG ‡ 268)为12.9 kcal / mol。在263 K的聚结温度下。1的夹杂物络合 与各种棒状脂肪酰胺和脂肪酯形成的主客体络合物以1:1的化学计量比形成,其中来宾的烷基链盘旋在空腔内,并通过CH /π与咪唑并喹喔啉瓣的扩大的芳族π表面相互作用而稳定。