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Conformational Control of [2]Rotaxane by Hydrogen Bond

[Image: see text] A series of [2]rotaxanes with various functional groups in the axle component was synthesized by the oxidative dimerization of alkynes, which is mediated by a macrocyclic phenanthroline–Cu complex. The rotaxanes were fully characterized by spectroscopic methods, and the structure o...

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Autores principales: Kawasaki, Yusuke, Rashid, Showkat, Ikeyatsu, Katsuhiko, Mutoh, Yuichiro, Yoshigoe, Yusuke, Kikkawa, Shoko, Azumaya, Isao, Hosoya, Shoichi, Saito, Shinichi
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9087201/
https://www.ncbi.nlm.nih.gov/pubmed/35389647
http://dx.doi.org/10.1021/acs.joc.2c00086
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author Kawasaki, Yusuke
Rashid, Showkat
Ikeyatsu, Katsuhiko
Mutoh, Yuichiro
Yoshigoe, Yusuke
Kikkawa, Shoko
Azumaya, Isao
Hosoya, Shoichi
Saito, Shinichi
author_facet Kawasaki, Yusuke
Rashid, Showkat
Ikeyatsu, Katsuhiko
Mutoh, Yuichiro
Yoshigoe, Yusuke
Kikkawa, Shoko
Azumaya, Isao
Hosoya, Shoichi
Saito, Shinichi
author_sort Kawasaki, Yusuke
collection PubMed
description [Image: see text] A series of [2]rotaxanes with various functional groups in the axle component was synthesized by the oxidative dimerization of alkynes, which is mediated by a macrocyclic phenanthroline–Cu complex. The rotaxanes were fully characterized by spectroscopic methods, and the structure of a rotaxane was determined by X-ray crystallographic analysis. The interaction between the ring component and the axle component was studied in detail to understand the conformation of the rotaxanes. The presence of the hydrogen bond between the phenanthroline moiety in the macrocyclic component and the acidic proton in the axle component influenced the conformation of rotaxane.
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spelling pubmed-90872012022-05-10 Conformational Control of [2]Rotaxane by Hydrogen Bond Kawasaki, Yusuke Rashid, Showkat Ikeyatsu, Katsuhiko Mutoh, Yuichiro Yoshigoe, Yusuke Kikkawa, Shoko Azumaya, Isao Hosoya, Shoichi Saito, Shinichi J Org Chem [Image: see text] A series of [2]rotaxanes with various functional groups in the axle component was synthesized by the oxidative dimerization of alkynes, which is mediated by a macrocyclic phenanthroline–Cu complex. The rotaxanes were fully characterized by spectroscopic methods, and the structure of a rotaxane was determined by X-ray crystallographic analysis. The interaction between the ring component and the axle component was studied in detail to understand the conformation of the rotaxanes. The presence of the hydrogen bond between the phenanthroline moiety in the macrocyclic component and the acidic proton in the axle component influenced the conformation of rotaxane. American Chemical Society 2022-04-07 2022-05-06 /pmc/articles/PMC9087201/ /pubmed/35389647 http://dx.doi.org/10.1021/acs.joc.2c00086 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Kawasaki, Yusuke
Rashid, Showkat
Ikeyatsu, Katsuhiko
Mutoh, Yuichiro
Yoshigoe, Yusuke
Kikkawa, Shoko
Azumaya, Isao
Hosoya, Shoichi
Saito, Shinichi
Conformational Control of [2]Rotaxane by Hydrogen Bond
title Conformational Control of [2]Rotaxane by Hydrogen Bond
title_full Conformational Control of [2]Rotaxane by Hydrogen Bond
title_fullStr Conformational Control of [2]Rotaxane by Hydrogen Bond
title_full_unstemmed Conformational Control of [2]Rotaxane by Hydrogen Bond
title_short Conformational Control of [2]Rotaxane by Hydrogen Bond
title_sort conformational control of [2]rotaxane by hydrogen bond
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9087201/
https://www.ncbi.nlm.nih.gov/pubmed/35389647
http://dx.doi.org/10.1021/acs.joc.2c00086
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