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Quantification and Prediction of Imine Formation Kinetics in Aqueous Solution by Microfluidic NMR Spectroscopy
Author(s) -
Zhuo Youzhen,
Wang Xiuxiu,
Chen Si,
Chen Hang,
Ouyang Jie,
Yang Liulin,
Wang Xinchang,
You Lei,
Utz Marcel,
Tian Zhongqun,
Cao Xiaoyu
Publication year - 2021
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202100874
Subject(s) - reactivity (psychology) , imine , chemistry , kinetics , aqueous solution , nuclear magnetic resonance spectroscopy , reaction rate constant , covalent bond , chemical kinetics , spectroscopy , reaction rate , microfluidics , organic chemistry , materials science , nanotechnology , catalysis , medicine , physics , alternative medicine , pathology , quantum mechanics
Quantitatively predicting the reactivity of dynamic covalent reaction is essential to understand and rationally design complex structures and reaction networks. Herein, the reactivity of aldehydes and amines in various rapid imine formation in aqueous solution by microfluidic NMR spectroscopy was quantified. Investigation of reaction kinetics allowed to quantify the forward rate constants k + by an empirical equation, of which three independent parameters were introduced as reactivity parameters of aldehydes ( S E , E ) and amines ( N ). Furthermore, these reactivity parameters were successfully used to predict the unknown forward rate constants of imine formation. Finally, two competitive reaction networks were rationally designed based on the proposed reactivity parameters. Our work has demonstrated the capability of microfluidic NMR spectroscopy in quantifying the kinetics of label‐free chemical reactions, especially rapid reactions that are complete in minutes.