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- W1976760910 abstract "The reactivity of proton-bound diastereomeric [M·H·A]+ complexes (A = amino acid; M = “strapped” tetra-amide macrocycle) towards the 2-aminobutane enantiomers (B) has been investigated in the gas phase by ESI-FT-ICR mass spectrometry. The displacement of the A guest from the diastereomeric [M·H·A]+ complexes by reaction with B exhibits a distinct enantioselectivity which markedly depend upon the presence of a π ring in A and on the nature of the intramolecular chain in the strapped macrocycle, whether –(CH2)10– (II) or –(C2H4O)5– (III). The emerging picture confirms the view that the chiral tetra-amide macrocycle II, characterized by an intramolecular decamethylene chain, may acquire in the gas phase a different conformation by induced fit on complexation of the selected A guests on the convex face of the host. This leads to the coexistence in the gas phase of stable diastereomeric [M·H·A]+ eq–eq and ax–ax structures, in proportions depending on the configuration of A and M and characterized by different stability and reactivity towards the 2-aminobutane enantiomers. When the decamethylene chain of the host is replaced by the –(CH2CH2O)5– chain, as in III, the guest A is blocked on the concave face of the host by complexation of its ammonium group by the “crown-ether”-like chain of the host and, therefore, the B-to-A displacement exhibits a more pronounced enantioselectivity." @default.
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- W1976760910 date "2011-05-26" @default.
- W1976760910 modified "2023-10-16" @default.
- W1976760910 title "Facial control of gas-phase enantioselectivity of strapped tetra-amide macrocycles" @default.
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- W1976760910 doi "https://doi.org/10.1007/s12210-011-0131-7" @default.
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