Anion binding to monotopic and ditopic macrocyclic amides

Ivan V. Korendovych; Mimi Cho; Phillip L. Butler; Richard J. Staples; Elena V. Rybak-Akimova

doi:10.1021/ol060786r

Anion binding to monotopic and ditopic macrocyclic amides

Ivan V. Korendovych, Mimi Cho, Phillip L. Butler, Richard J. Staples, Elena V. Rybak-Akimova

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

60 Scopus citations

Abstract

Binding of fluoride anion as well as carboxylic acid tetraalkylammonium salts by macrocyclic compounds of different size was studied by NMR in DMSO-d₆. It has been found that at least a 15-membered ring is necessary for successful recognition of fluoride. Larger macrocycles obtained in a [2 + 2] cyclization were shown to bind dicarboxylic acid salts. Effects of binding topicity are discussed.

Original language	English (US)
Pages (from-to)	3171-3174
Number of pages	4
Journal	Organic Letters
Volume	8
Issue number	15
DOIs	https://doi.org/10.1021/ol060786r
State	Published - Jul 20 2006
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol060786r

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abstract = "Binding of fluoride anion as well as carboxylic acid tetraalkylammonium salts by macrocyclic compounds of different size was studied by NMR in DMSO-d6. It has been found that at least a 15-membered ring is necessary for successful recognition of fluoride. Larger macrocycles obtained in a [2 + 2] cyclization were shown to bind dicarboxylic acid salts. Effects of binding topicity are discussed.",

author = "Korendovych, {Ivan V.} and Mimi Cho and Butler, {Phillip L.} and Staples, {Richard J.} and Rybak-Akimova, {Elena V.}",

year = "2006",

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language = "English (US)",

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T1 - Anion binding to monotopic and ditopic macrocyclic amides

AU - Korendovych, Ivan V.

AU - Cho, Mimi

AU - Butler, Phillip L.

AU - Staples, Richard J.

AU - Rybak-Akimova, Elena V.

PY - 2006/7/20

Y1 - 2006/7/20

N2 - Binding of fluoride anion as well as carboxylic acid tetraalkylammonium salts by macrocyclic compounds of different size was studied by NMR in DMSO-d6. It has been found that at least a 15-membered ring is necessary for successful recognition of fluoride. Larger macrocycles obtained in a [2 + 2] cyclization were shown to bind dicarboxylic acid salts. Effects of binding topicity are discussed.

AB - Binding of fluoride anion as well as carboxylic acid tetraalkylammonium salts by macrocyclic compounds of different size was studied by NMR in DMSO-d6. It has been found that at least a 15-membered ring is necessary for successful recognition of fluoride. Larger macrocycles obtained in a [2 + 2] cyclization were shown to bind dicarboxylic acid salts. Effects of binding topicity are discussed.

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U2 - 10.1021/ol060786r

DO - 10.1021/ol060786r

M3 - Article

C2 - 16836358

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SN - 1523-7060

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JO - Organic Letters

JF - Organic Letters

IS - 15

ER -

Anion binding to monotopic and ditopic macrocyclic amides

Abstract

ASJC Scopus subject areas

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