中文版 | English
Title

Stabilization of Imines and Hemiaminals in Water by an Endo-Functionalized Container Molecule

Author
Corresponding AuthorJiang, Wei
Publication Years
2022-07-01
DOI
Source Title
ISSN
1433-7851
EISSN
1521-3773
Volume61
Abstract
Stabilizing water-sensitive reaction intermediates is challenging but desirable for guiding reactions to desired products in water. Herein, we report that labile imine and hemiaminal functional groups can be stabilized inside a synthetic container compound, a water-soluble naphthotube. The naphthotube features a primary amine group anchored in a cavity with both hydrogen bonding sites and hydrophobic surfaces. Aldehydes in bulk aqueous solution are trapped in the cavity by the amine to form hemiaminals stabilized through hydrogen bonding and hydrophobic effects. Dehydration of the hemiaminal to the imine is favored by the release of water from the hydrophobic microenvironment. Both the hemiaminals and imines can be detected at room temperature by NMR spectroscopy and mass spectrometry.
Keywords
URL[Source Record]
Indexed By
SCI ; EI
Language
English
Important Publications
NI Journal Papers
SUSTech Authorship
Corresponding
Funding Project
National Natural Science Foundation of China[22125105] ; Guangdong High-Level Personnel of Special Support Program[2019TX05C157] ; Guangdong Provincial Key Laboratory of Catalysis[2020B121201002]
WOS Research Area
Chemistry
WOS Subject
Chemistry, Multidisciplinary
WOS Accession No
WOS:000826547400001
Publisher
EI Accession Number
20223112455393
EI Keywords
Amines ; Hydrogen ; Hydrogen bonds ; Hydrophobicity ; Mass spectrometry ; Nuclear magnetic resonance spectroscopy ; Reaction intermediates ; Surface chemistry
ESI Classification Code
Chemistry:801 ; Physical Chemistry:801.4 ; Chemical Products Generally:804 ; Organic Compounds:804.1 ; Physical Properties of Gases, Liquids and Solids:931.2
ESI Research Field
CHEMISTRY
Data Source
Web of Science
Citation statistics
Cited Times [WOS]:1
Document TypeJournal Article
Identifierhttp://kc.sustech.edu.cn/handle/2SGJ60CL/356164
DepartmentShenzhen Grubbs Institute
理学院_化学系
Affiliation
1.Harbin Inst Technol, Sch Chem & Chem Engn, 92 Xidazhi St, Harbin 150001, Peoples R China
2.Southern Univ Sci & Technol SUSTech, Shenzhen Grubbs Inst, Guangdong Prov Key Lab Catalysis, Xueyuan Blvd 1088, Shenzhen 518055, Peoples R China
3.Southern Univ Sci & Technol SUSTech, Dept Chem, Xueyuan Blvd 1088, Shenzhen 518055, Peoples R China
First Author AffilicationShenzhen Grubbs Institute;  Department of Chemistry
Corresponding Author AffilicationShenzhen Grubbs Institute;  Department of Chemistry
Recommended Citation
GB/T 7714
Li, Ming-Shuang,Dong, Yi-Wei,Quan, Mao,et al. Stabilization of Imines and Hemiaminals in Water by an Endo-Functionalized Container Molecule[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,2022,61.
APA
Li, Ming-Shuang,Dong, Yi-Wei,Quan, Mao,&Jiang, Wei.(2022).Stabilization of Imines and Hemiaminals in Water by an Endo-Functionalized Container Molecule.ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,61.
MLA
Li, Ming-Shuang,et al."Stabilization of Imines and Hemiaminals in Water by an Endo-Functionalized Container Molecule".ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 61(2022).
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