Reaction Mechanism of 2-Amido-2-Aminoacetic Acid-Formation from Amides and 2-Iminoacetic Acid: A DFT-study and Wavefunction Analysis

10.26434/chemrxiv.13347545.v2 ◽

2021 ◽

Author(s):

Georg Dazinger

Keyword(s):

Reaction Mechanism ◽

Dft Study ◽

Acid Formation ◽

Side Reactions ◽

Aminoacetic Acid ◽

Diamino Acid ◽

Wavefunction Analysis ◽

Acid Esters

Based on a study of Wei Zeng et. al.[7], where the synthesis of gem-diamino acid esters from 2-iminoacetic acid esters and amides, with various N- and C-substituents, respectively, is reported, a modeled reaction, where the latter substituents were replaced by H, was simulated by means of DFT. A reasonable reaction mechanism was found for the formation of 2-amido-2-aminoacetic acid from formamide and 2-iminoacetic acid. Moreover, possible side reactions were simulated and discussed.

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Reaction Mechanism of 2-Amido-2-Aminoacetic Acid-Formation from Amides and 2-Iminoacetic Acid: A DFT-study and Wavefunction Analysis

10.26434/chemrxiv.13347545.v1 ◽

2020 ◽

Author(s):

Georg Dazinger

Keyword(s):

Reaction Mechanism ◽

Dft Study ◽

Acid Formation ◽

Side Reactions ◽

Aminoacetic Acid ◽

Diamino Acid ◽

Wavefunction Analysis ◽

Acid Esters

Based on a study of Wei Zeng et. al.[7], where the synthesis of gem-diamino acid esters from 2-iminoacetic acid esters and amides, with various N- and C-substituents, respectively, is reported, a modeled reaction, where the latter substituents were replaced by H, was simulated by means of DFT. A reasonable reaction mechanism was found for the formation of 2-amido-2-aminoacetic acid from formamide and 2-iminoacetic acid. Moreover, possible side reactions were simulated and discussed.

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An intramolecular oxa-Michael reaction on α,β-unsaturated α-amino-δ-hydroxycarboxylic acid esters. Synthesis of functionalized 1,3-dioxanes

Organic & Biomolecular Chemistry ◽

10.1039/c7ob03066e ◽

2018 ◽

Vol 16 (8) ◽

pp. 1277-1286 ◽

Cited By ~ 6

Author(s):

L. Becerra-Figueroa ◽

S. Movilla ◽

J. Prunet ◽

G. P. Miscione ◽

D. Gamba-Sánchez

Keyword(s):

Reaction Mechanism ◽

Michael Reaction ◽

Experimental Results ◽

Dft Study ◽

Selective Method ◽

Hydroxycarboxylic Acid ◽

Acid Esters

A simple and selective method to access 1,3-dioxanes functionalized in positions 2,4 and 6 has been developed. The experimental results are complemented with a DFT study on the reaction mechanism, which illustrates the reaction course and explains the reactivity and selectivity.

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Enzymatic Synthesis of Muconic Acid-Based Polymers: Trans, Trans-Dimethyl Muconate and Trans, β-Dimethyl Hydromuconate

Polymers ◽

10.3390/polym13152498 ◽

2021 ◽

Vol 13 (15) ◽

pp. 2498

Author(s):

Dina Maniar ◽

Csaba Fodor ◽

Indra Karno Adi ◽

Albert J. J. Woortman ◽

Jur van Dijken ◽

...

Keyword(s):

Reaction Mechanism ◽

Renewable Resources ◽

Enzymatic Synthesis ◽

Enzyme Catalysis ◽

Unsaturated Polyester ◽

Chain Extension ◽

Side Reactions ◽

Muconic Acid ◽

Thermal Stabilities ◽

Polyester Resins

The vast majority of commodity polymers are acquired from petrochemical feedstock, and these resources will plausibly be depleted within the next 100 years. Therefore, the utilization of carbon-neutral renewable resources for the production of polymers is crucial in modern green chemistry. Herein, we report an eco-friendly strategy that uses enzyme catalysis to design biobased unsaturated (co)polyesters from muconic acid derivatives. This method is an attractive pathway for the production of well-defined unsaturated polyesters with minimum side reactions. A suite of characterization techniques was performed to probe the reaction mechanism and properties of the obtained polyesters. It is rationalized that the alkene functionality of the muconate monomers plays an important role in the enzyme catalysis mechanism. The rendered polyesters possessed excellent thermal stabilities and unreacted alkene functionality that can consecutively undergo chain extension, copolymerization, or act as an anchor for other functional groups. These properties open new avenues in the fields of unsaturated polyester resins and photosensitive coatings.

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