Investigation on the hydrolytic mechanism of cucurbit[6]uril in alkaline solution

Chao Zhu; Zihui Meng; Wenjin Liu; Hongwei Ma; Jiarong Li; Tongtong Yang; Yang Liu; Ni Liu; Zhibin Xu

doi:10.1098/rsos.180038

Investigation on the hydrolytic mechanism of cucurbit[6]uril in alkaline solution

Chao Zhu, Zihui Meng, Wenjin Liu, Hongwei Ma, Jiarong Li, Tongtong Yang, Yang Liu, Ni Liu, Zhibin Xu^*

^*Corresponding author for this work

School of Chemistry and Chemical Engineering

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

3 Citations (Scopus)

Abstract

The structure of cucurbit[6]uril (CB[6]), as a fascinating supramolecular receptor, is regarded as ‘indestructible’. Herein, we investigated the hydrolysis of CB[6] catalysed by alkali. Our results showed that CB[6] was easily hydrolysed in 30% NaOH at 160°C within 3 h. Separation and purification of hydrolytic products demonstrated the presence of NH₃, CO₂, HCOONa, glycine and hydantoic acid. Based on the studies of the hydrolysis of substances similar to CB[6] including 4,5-dihydroxyethyleneurea, glycoluril and glycoluril dimer, we proposed that a plausible reaction mechanism involved a Cannizzaro reaction, which is supported by HPLC, mass spectrometry data and previous reports. Further studies are dedicated towards a controlled hydrolysis of CB[6], which will provide a new route for direct functionalization of CB[6].

Original language	English
Article number	180038
Journal	Royal Society Open Science
Volume	5
Issue number	5
DOIs	https://doi.org/10.1098/rsos.180038
Publication status	Published - 2 May 2018

Keywords

Cucurbit[6]uril
Hydrolysis reaction
Mechanism research
Product separation

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10.1098/rsos.180038

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title = "Investigation on the hydrolytic mechanism of cucurbit[6]uril in alkaline solution",

abstract = "The structure of cucurbit[6]uril (CB[6]), as a fascinating supramolecular receptor, is regarded as {\textquoteleft}indestructible{\textquoteright}. Herein, we investigated the hydrolysis of CB[6] catalysed by alkali. Our results showed that CB[6] was easily hydrolysed in 30% NaOH at 160°C within 3 h. Separation and purification of hydrolytic products demonstrated the presence of NH3, CO2, HCOONa, glycine and hydantoic acid. Based on the studies of the hydrolysis of substances similar to CB[6] including 4,5-dihydroxyethyleneurea, glycoluril and glycoluril dimer, we proposed that a plausible reaction mechanism involved a Cannizzaro reaction, which is supported by HPLC, mass spectrometry data and previous reports. Further studies are dedicated towards a controlled hydrolysis of CB[6], which will provide a new route for direct functionalization of CB[6].",

keywords = "Cucurbit[6]uril, Hydrolysis reaction, Mechanism research, Product separation",

author = "Chao Zhu and Zihui Meng and Wenjin Liu and Hongwei Ma and Jiarong Li and Tongtong Yang and Yang Liu and Ni Liu and Zhibin Xu",

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doi = "10.1098/rsos.180038",

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T1 - Investigation on the hydrolytic mechanism of cucurbit[6]uril in alkaline solution

AU - Zhu, Chao

AU - Meng, Zihui

AU - Liu, Wenjin

AU - Ma, Hongwei

AU - Li, Jiarong

AU - Yang, Tongtong

AU - Liu, Yang

AU - Liu, Ni

AU - Xu, Zhibin

PY - 2018/5/2

Y1 - 2018/5/2

N2 - The structure of cucurbit[6]uril (CB[6]), as a fascinating supramolecular receptor, is regarded as ‘indestructible’. Herein, we investigated the hydrolysis of CB[6] catalysed by alkali. Our results showed that CB[6] was easily hydrolysed in 30% NaOH at 160°C within 3 h. Separation and purification of hydrolytic products demonstrated the presence of NH3, CO2, HCOONa, glycine and hydantoic acid. Based on the studies of the hydrolysis of substances similar to CB[6] including 4,5-dihydroxyethyleneurea, glycoluril and glycoluril dimer, we proposed that a plausible reaction mechanism involved a Cannizzaro reaction, which is supported by HPLC, mass spectrometry data and previous reports. Further studies are dedicated towards a controlled hydrolysis of CB[6], which will provide a new route for direct functionalization of CB[6].

AB - The structure of cucurbit[6]uril (CB[6]), as a fascinating supramolecular receptor, is regarded as ‘indestructible’. Herein, we investigated the hydrolysis of CB[6] catalysed by alkali. Our results showed that CB[6] was easily hydrolysed in 30% NaOH at 160°C within 3 h. Separation and purification of hydrolytic products demonstrated the presence of NH3, CO2, HCOONa, glycine and hydantoic acid. Based on the studies of the hydrolysis of substances similar to CB[6] including 4,5-dihydroxyethyleneurea, glycoluril and glycoluril dimer, we proposed that a plausible reaction mechanism involved a Cannizzaro reaction, which is supported by HPLC, mass spectrometry data and previous reports. Further studies are dedicated towards a controlled hydrolysis of CB[6], which will provide a new route for direct functionalization of CB[6].

KW - Cucurbit[6]uril

KW - Hydrolysis reaction

KW - Mechanism research

KW - Product separation

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DO - 10.1098/rsos.180038

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AN - SCOPUS:85046540087

SN - 2054-5703

VL - 5

JO - Royal Society Open Science

JF - Royal Society Open Science

IS - 5

M1 - 180038

ER -

Investigation on the hydrolytic mechanism of cucurbit[6]uril in alkaline solution

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Keywords

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