Lithium ion-selective binding properties of a conformationally constrained tris(spirotetrahydrofuran) secured to an inositol orthoformate platform

Jinsung Tae; Robin D. Rogers; Leo A. Paquette

doi:10.1021/ol990342d

Lithium ion-selective binding properties of a conformationally constrained tris(spirotetrahydrofuran) secured to an inositol orthoformate platform

Jinsung Tae, Robin D. Rogers, Leo A. Paquette

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

26 Citations (Scopus)

Abstract

(equation presented) The C_3v-symmetric triaxially locked trispirotetrahydrofuran 2 binds Li⁺ ions strongly and Na⁺ ions much less effectively. The observed discrimination factor is attributed to greater structural preorganiztion and lower solvation prior to selective complexation, and particularly to the formation of a 2:1 sandwich complex involving lithium. ¹³C NMR studies have defined a reluctance to form a 1:1 species when excess Li⁺ is present.

Original language	English
Pages (from-to)	139-142
Number of pages	4
Journal	Organic Letters
Volume	2
Issue number	2
DOIs	https://doi.org/10.1021/ol990342d
Publication status	Published - 2000 Jan 27

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol990342d

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abstract = "(equation presented) The C3v-symmetric triaxially locked trispirotetrahydrofuran 2 binds Li+ ions strongly and Na+ ions much less effectively. The observed discrimination factor is attributed to greater structural preorganiztion and lower solvation prior to selective complexation, and particularly to the formation of a 2:1 sandwich complex involving lithium. 13C NMR studies have defined a reluctance to form a 1:1 species when excess Li+ is present.",

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AB - (equation presented) The C3v-symmetric triaxially locked trispirotetrahydrofuran 2 binds Li+ ions strongly and Na+ ions much less effectively. The observed discrimination factor is attributed to greater structural preorganiztion and lower solvation prior to selective complexation, and particularly to the formation of a 2:1 sandwich complex involving lithium. 13C NMR studies have defined a reluctance to form a 1:1 species when excess Li+ is present.

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