| Title | Stabilization of Imines and Hemiaminals in Water by an Endo-Functionalized Container Molecule |
| Author | |
| Corresponding Author | Jiang, Wei |
| Publication Years | 2022-07-01
|
| DOI | |
| Source Title | |
| ISSN | 1433-7851
|
| EISSN | 1521-3773
|
| Volume | 61 |
| 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 | |
| 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]:3
|
| Document Type | Journal Article |
| Identifier | http://kc.sustech.edu.cn/handle/2SGJ60CL/356164 |
| Department | Shenzhen 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 Affilication | Shenzhen Grubbs Institute; Department of Chemistry |
| Corresponding Author Affilication | Shenzhen 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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