Synthesis and conformational studies of an asymmetrical dibenzo-16-crown-5 carboxylic acid

Jong Seung Kim; Richard A. Bartsch; Visvanathan Ramesh

doi:10.1023/A:1008078220916

Synthesis and conformational studies of an asymmetrical dibenzo-16-crown-5 carboxylic acid

Jong Seung Kim, Richard A. Bartsch, Visvanathan Ramesh

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

2 Citations (Scopus)

Abstract

Asymmetrical cis-5,6-dimethyl-6-oxyacetoxy-(2,3)(9,10)-dibenzo-16-crown-5 was synthesized by a multi-step sequence and its stereochemistry determined by NOE experiments. Introduction of the 6-methyl group markedly reduces the stability constant for complexation of Na⁺ and K⁺ by the ionized form of the lariat ether carboxylic acid.

Original language	English
Pages (from-to)	287-299
Number of pages	13
Journal	Journal of Inclusion Phenomena
Volume	36
Issue number	3
DOIs	https://doi.org/10.1023/A:1008078220916
Publication status	Published - 2000 Mar
Externally published	Yes

Bibliographical note

Funding Information:
This research was supported by the Division of Chemical Sciences of the Office of Basic Sciences of the US department of Energy through grant DE-FG03-94ER14416.

Keywords

Complexation
Crown ether
NMR

ASJC Scopus subject areas

Food Science
General Chemistry
Condensed Matter Physics

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10.1023/A:1008078220916

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title = "Synthesis and conformational studies of an asymmetrical dibenzo-16-crown-5 carboxylic acid",

abstract = "Asymmetrical cis-5,6-dimethyl-6-oxyacetoxy-(2,3)(9,10)-dibenzo-16-crown-5 was synthesized by a multi-step sequence and its stereochemistry determined by NOE experiments. Introduction of the 6-methyl group markedly reduces the stability constant for complexation of Na+ and K+ by the ionized form of the lariat ether carboxylic acid.",

keywords = "Complexation, Crown ether, NMR",

author = "Kim, {Jong Seung} and Bartsch, {Richard A.} and Visvanathan Ramesh",

note = "Funding Information: This research was supported by the Division of Chemical Sciences of the Office of Basic Sciences of the US department of Energy through grant DE-FG03-94ER14416.",

year = "2000",

month = mar,

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T1 - Synthesis and conformational studies of an asymmetrical dibenzo-16-crown-5 carboxylic acid

AU - Kim, Jong Seung

AU - Bartsch, Richard A.

AU - Ramesh, Visvanathan

N1 - Funding Information: This research was supported by the Division of Chemical Sciences of the Office of Basic Sciences of the US department of Energy through grant DE-FG03-94ER14416.

PY - 2000/3

Y1 - 2000/3

N2 - Asymmetrical cis-5,6-dimethyl-6-oxyacetoxy-(2,3)(9,10)-dibenzo-16-crown-5 was synthesized by a multi-step sequence and its stereochemistry determined by NOE experiments. Introduction of the 6-methyl group markedly reduces the stability constant for complexation of Na+ and K+ by the ionized form of the lariat ether carboxylic acid.

AB - Asymmetrical cis-5,6-dimethyl-6-oxyacetoxy-(2,3)(9,10)-dibenzo-16-crown-5 was synthesized by a multi-step sequence and its stereochemistry determined by NOE experiments. Introduction of the 6-methyl group markedly reduces the stability constant for complexation of Na+ and K+ by the ionized form of the lariat ether carboxylic acid.

KW - Complexation

KW - Crown ether

KW - NMR

UR - http://www.scopus.com/inward/record.url?scp=0034147757&partnerID=8YFLogxK

U2 - 10.1023/A:1008078220916

DO - 10.1023/A:1008078220916

M3 - Article

AN - SCOPUS:0034147757

SN - 0923-0750

VL - 36

SP - 287

EP - 299

JO - Journal of Inclusion Phenomena

JF - Journal of Inclusion Phenomena

IS - 3

ER -

Synthesis and conformational studies of an asymmetrical dibenzo-16-crown-5 carboxylic acid

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

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