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

Li, Ming-Shuang1,2,3; Dong, Yi-Wei2,3; Quan, Mao2,3; Jiang, Wei2,3

2022-07-01

10.1002/anie.202208508

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION   影响因子和分区

1433-7851

1521-3773

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.

Hemiaminals Imines Naphthotube Water-Sensitive Intermediates

SCI ; EI

英语

NI论文

通讯

National Natural Science Foundation of China[22125105] ; Guangdong High-Level Personnel of Special Support Program[2019TX05C157] ; Guangdong Provincial Key Laboratory of Catalysis[2020B121201002]

Chemistry

Chemistry, Multidisciplinary

WOS:000826547400001

WILEY-V C H VERLAG GMBH

20223112455393

Amines ; Hydrogen ; Hydrogen bonds ; Hydrophobicity ; Mass spectrometry ; Nuclear magnetic resonance spectroscopy ; Reaction intermediates ; Surface chemistry

Chemistry:801 ; Physical Chemistry:801.4 ; Chemical Products Generally:804 ; Organic Compounds:804.1 ; Physical Properties of Gases, Liquids and Solids:931.2

CHEMISTRY

Web of Science

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

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.

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.

Li, Ming-Shuang,et al."Stabilization of Imines and Hemiaminals in Water by an Endo-Functionalized Container Molecule".ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 61(2022).