Publication Date:
2008
Citation:
Reactivity of anionic nucleophiles in ionic liquids and in molecular solvents / C. Betti, D. Landini, A. Maia. - In: TETRAHEDRON. - ISSN 0040-4020. - 64:8(2008), pp. 1689-1695. [10.1016/j.tet.2007.12.009]
abstract:
The nucleophilic reactivity of a representative series of anions has been measured in [hmim][ClO4] 3i, [hm2im][ClO4] 30i, and [hmim][PF6]
3l ILs in the reaction with n-alkyl methanesulfonates and compared with that found in common molecular solvents (MeOH, DMSO, PhCl). The
reactivity is found to depend on both the imidazolium cationeanion interaction and the specific solvation by water present in the IL, the water
playing the main effect, in particular with hydrophilic anions. Removal of the largest quantity of water remarkably increases the ion pair
reactivity in the IL up to rate constant value k comparable with those obtained in DMSO and in low polarity media (PhCl).
3l ILs in the reaction with n-alkyl methanesulfonates and compared with that found in common molecular solvents (MeOH, DMSO, PhCl). The
reactivity is found to depend on both the imidazolium cationeanion interaction and the specific solvation by water present in the IL, the water
playing the main effect, in particular with hydrophilic anions. Removal of the largest quantity of water remarkably increases the ion pair
reactivity in the IL up to rate constant value k comparable with those obtained in DMSO and in low polarity media (PhCl).
IRIS type:
01 - Articolo su periodico
Keywords:
Ionic liquids ; nucleophilic substitutions ; anionic reactivity ; alkyl methanesulfonates
List of contributors:
C. Betti, D. Landini, M. A.
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