ArticleChemistry (Weinheim an der Bergstrasse, Germany)2020
Configurational and Constitutional Dynamics of Enamine Molecular Switches.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 3 papers.
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3 citing papers in PubMed.
- Formation of Zwitterionic and Self-Healable Hydrogels via Amino-yne Click Chemistry for Development of Cellular Scaffold and Tumor Spheroid Phantom for MRI.ACS applied materials & interfaces · 2024Article
- A Spectroscopic Overview of Intramolecular Hydrogen Bonds of NH…O,S,N Type.Molecules (Basel, Switzerland) · 2021Review
- Configurational and Constitutional Dynamics of Enamine Molecular Switches.Chemistry (Weinheim an der Bergstrasse, Germany) · 2020Article
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Abstract
Dual configurational and constitutional dynamics in systems based on enamine molecular switches has been systematically studied. pH-responsive moieties, such as 2-pyridyl and 2-quinolinyl units, were required on the "stator" part, also providing enamine stability through intramolecular hydrogen-bonding (IMHB) effects. Upon protonation or deprotonation, forward and backward switching could be rapidly achieved. Extension of the stator π-system in the 2-quinolinyl derivative provided a higher E-isomeric equilibrium ratio under neutral conditions, pointing to a means to achieve quantitative forward/backward isomerization processes. The "rotor" part of the enamine switches exhibited constitutional exchange ability with primary amines. Interestingly, considerably higher exchange rates were observed with amines containing ester groups, indicating potential stabilization of the transition state through IMHB. Acids, particularly Bi
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