Inclusion complexation of a deep cavitand with imidazoquinoxaline flaps forming stable vase-like conformation

Autor:	Heung-Jin Choi, Suban K. Sahoo, Quoc-Thiet Nguyen
Rok vydání:	2018
Předmět:	chemistry.chemical_classification 010405 organic chemistry Organic Chemistry Cavitand Activation energy 010402 general chemistry 01 natural sciences Biochemistry Tautomer 0104 chemical sciences Crystallography chemistry Drug Discovery Proton NMR Stoichiometry Alkyl
Zdroj:	Tetrahedron. 74:1759-1766
ISSN:	0040-4020
DOI:	10.1016/j.tet.2018.01.049
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::064c033e3a2fac813af00a5e7f438ee8 https://doi.org/10.1016/j.tet.2018.01.049 Zobrazit plný text záznamu Full Text from ScienceDirect