Inclusion complexation of a deep cavitand with imidazoquinoxaline flaps forming stable vase-like conformation. Issue 15 (12th April 2018)

• Record Type: Journal Article
• Authors: Nguyen, Quoc-Thiet; Sahoo, Suban K.; Choi, Heung-Jin
• Is Part Of: Tetrahedron. Volume 74:Issue 15(2018)
• Page Start: 1759
• Page End: 1766
• Publication Date: 2018-04-12
• Subjects: Imidazoquinoxaline cavitand -- Deep cavitand -- CH/π interactions -- Inclusion complexation -- Annular tautomerism; WAIOKONZHHXUIK-FQVOSWEDSA-N; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2018.01.049
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: The stability of the vase-like conformation of a deep cavitand1 with four imidazoquinoxaline flaps was studied in CDCl3 /CD3 OD by 1 H NMR method. The annular tautomerism of cavitand1 ·4MeOD in CDCl3 /CD3 OD (1:9 v/v) was investigated by 1 H 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 of1 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. Graphical abstract: