Can the absence of solvation of neutral reagents by ionic liquids be responsible for the high reactivity in base-assisted intramolecular nucleophilic substitutions in these solvents?

Autor:	Domenico Spinelli, Renato Noto, Francesca D'Anna, Vitalba Pace, Vincenzo Frenna
Přispěvatelé:	F. D'ANNA, V. FRENNA, R. NOTO, V. PACE, SPINELLI D., D'ANNA F, FRENNA V, NOTO R, PACE V, SPINELLI D
Jazyk:	angličtina
Rok vydání:	2005
Předmět:	ionic liquids mononuclear rearrangement of heterocycles base catalysis Organic Chemistry Solvation Solvent chemistry.chemical_compound chemistry Nucleophile Computational chemistry Intramolecular force Ionic liquid Nucleophilic substitution Organic chemistry Reactivity (chemistry) Solvent effects
Popis:	[reaction: see text] The kinetics of the rearrangement of the Z-phenylhydrazone of 3-benzoyl-5-phenyl-1,2,4-oxadiazole (1a) into the relevant 4-benzoylamino-2,5-diphenyl-1,2,3-triazole (2a) induced by amines have been studied in two room-temperature ionic liquids (IL-1, [BMIM][BF4] and IL-2, [BMIM][PF6]). The data collected show that the reaction occurs faster in ionic liquids than in other conventional solvents previously studied (both polar or apolar, protic or aprotic). Presumably, this could depend on their peculiar ability to minimize the strong substrate-solvent, amine-solvent and amine-amine interactions occurring in conventional solvents.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::ffe808e073f9feb8571f5e93947bf744 http://hdl.handle.net/11585/2553 Zobrazit plný text záznamu