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Issue 27, 2019
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Synthesis of per(5-N-carboxamide-5-dehydroxylmethyl)-β-cyclodextrins and their selective recognition ability utilizing multiple hydrogen bonds†

Takashi Nakamura, ORCID logo a   Sota Yonemuraa  and  Tatsuya Nabeshima ORCID logo *a  
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* Corresponding authors

a Graduate School of Pure and Applied Sciences and Tsukuba Research Center for Energy Materials Science (TREMS), University of Tsukuba, 1-1-1 Tennodai, Tsukuba, Ibaraki 305-8571, Japan
E-mail: nabesima@chem.tsukuba.ac.jp

Abstract

Per(5-N-carboxamide-5-dehydroxylmethyl)-β-cyclodextrin derivatives with seven equivalent amide groups directly attached to each pyranose ring were synthesized. The amide cyclodextrins show unique recognition properties toward hydrogen phosphonate anions. An X-ray crystallographic analysis revealed its recognition mode in which unsymmetrically arranged amide groups play distinctive roles both as a hydrogen bond donor and acceptor.

Graphical abstract: Synthesis of per(5-N-carboxamide-5-dehydroxylmethyl)-β-cyclodextrins and their selective recognition ability utilizing multiple hydrogen bonds

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Article information

https://doi.org/10.1039/C9CC00517J
Submitted
21 Jan 2019
Accepted
19 Feb 2019
First published
19 Feb 2019
Chem. Commun., 2019,55, 3872-3875
Article type
Communication
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Synthesis of per(5-N-carboxamide-5-dehydroxylmethyl)-β-cyclodextrins and their selective recognition ability utilizing multiple hydrogen bonds

T. Nakamura, S. Yonemura and T. Nabeshima, Chem. Commun., 2019, 55, 3872
DOI: 10.1039/C9CC00517J

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