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Related Concept Videos

Structure of Amines01:19

Structure of Amines

2.6K
The hybridized nitrogen atom in amines possesses a lone pair of electrons and is bound to three substituents with a bond angle of around 108°, which is less than the tetrahedral angle of 109.5°. However, the C–N–H bond angle is slightly larger at 112°, with a carbon–nitrogen bond length of 147 pm. This carbon–nitrogen bond length of of amines is longer than the carbon–oxygen bond of alcohols (143 pm) but shorter than alkanes’...
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Basicity of Aromatic Amines01:18

Basicity of Aromatic Amines

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The basicity of aromatic amines is much weaker than that of aliphatic amines due to the involvement of the lone pair of electrons over the N atom in resonance with the aryl rings. Generally, the electron-donating ability of any substituents on the aryl ring of aromatic amines increases the basicity of the amine by increasing electron density, and hence the availability of lone pair on the nitrogen. On the other hand, electron-withdrawing functional groups on the aryl ring of amines decrease the...
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Basicity of Heterocyclic Aromatic Amines01:25

Basicity of Heterocyclic Aromatic Amines

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Heterocyclic amines, where the N atom is a part of an alicyclic system, are similar in basicity to alkylamines. Interestingly, the heterocyclic amine having a nitrogen atom as part of an aromatic ring has much less basicity than its corresponding alicyclic counterpart. For this reason, as presented in Figure 1, piperidine (pKb = 2.8) is significantly more basic than pyridine (pKb = 8.8).
6.2K
Preparation of Amines: Alkylation of Ammonia and Amines01:30

Preparation of Amines: Alkylation of Ammonia and Amines

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Alkylation is one of the methods used to prepare amines. Direct alkylation of ammonia or a primary amine with an alkyl halide gives polyalkylated amines along with a quaternary ammonium salt through successive SN2 reactions. This process of making the quaternary salt through the direct alkylation method is called exhaustive alkylation.
Each alkylation step makes the nitrogen center more nucleophilic, which triggers successive alkylations until a quaternary ammonium salt is formed. Considering...
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Physical Properties of Amines01:26

Physical Properties of Amines

3.3K
Amines with low molecular weight are usually gaseous at room temperature, while those with high molecular weight are liquid or solids in nature. Usually, low molecular weight amines have a rotten fish-like smell. Diamines typically have a pungent smell. For instance, cadaverine and putrescine, depicted in Figure 1, are two molecules responsible for decaying tissue.
3.3K
Basicity of Aliphatic Amines01:21

Basicity of Aliphatic Amines

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Amines can behave as Brønsted–Lowry bases by accepting a proton from the acid to form corresponding conjugate acids. Due to a lone pair of nonbonding electrons, aliphatic amines can also act as Lewis bases by forming a covalent bond with an electrophile.
To measure the basicity of amines, two conventions are generally used. The first defines Kb as the basicity constant for the deprotonation reaction of water by the amine, as presented in Figure 1. Conventionally, lower Kb indicates...
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Ethylene Polymerizations Using Parallel Pressure Reactors and a Kinetic Analysis of Chain Transfer Polymerization
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Ethylene Polymerizations Using Parallel Pressure Reactors and a Kinetic Analysis of Chain Transfer Polymerization

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Variable Amine Spacing Determines Depolymerization Rate in Polydiketoenamines.

Alexander R Epstein1, Jeremy Demarteau2, Brett A Helms2,3,4

  • 1Materials Sciences and Engineering, University of California, Berkeley, Berkeley, California 94720, United States.

Journal of the American Chemical Society
|March 28, 2023
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Summary
This summary is machine-generated.

Circular polymers like polydiketoenamines (PDKs) enable efficient plastic recycling. A proximal amine in the cross-linker significantly speeds up PDK depolymerization, enhancing material circularity.

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Area of Science:

  • Polymer Chemistry
  • Materials Science
  • Sustainable Chemistry

Background:

  • Efficient recycling methods for commodity plastics, especially in durable goods, are lacking.
  • Circular polymers offer a sustainable alternative to conventional plastics.
  • Polydiketoenamines (PDKs) are promising due to their selective acid-catalyzed depolymerization for monomer recovery.

Purpose of the Study:

  • To investigate the effect of cross-linker chemistry on the depolymerization rate of polydiketoenamines (PDKs).
  • To understand the molecular basis governing the circularity of PDKs.
  • To identify new design strategies for amine monomers to enhance PDK properties and recyclability.

Main Methods:

  • Synthesis of polydiketoenamine (PDK) variants with varying cross-linker structures.
  • Acid-catalyzed depolymerization experiments to measure reaction rates.
  • Analysis of the influence of cross-linker functionality and spacing on depolymerization kinetics.

Main Results:

  • The presence of a proximal amine group in the cross-linker significantly accelerates PDK depolymerization compared to non-amine cross-linkers.
  • The spacing between the amine group and the diketoenamine linkage modulates the depolymerization rate.
  • This finding reveals a key factor in controlling the chemical recyclability of PDKs.

Conclusions:

  • Cross-linker design, specifically the inclusion and positioning of amine groups, is critical for tuning PDK depolymerization rates.
  • Understanding these structure-property relationships is essential for designing next-generation circular polymers.
  • This research provides a molecular basis for enhancing the chemical recycling and material diversity of polydiketoenamines.