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Factors Affecting α-Alkylation of Ketones: Choice of Base01:10

Factors Affecting α-Alkylation of Ketones: Choice of Base

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α-Alkylation of ketones is achieved in the presence of alkyl halides and a base. The reaction proceeds via the formation of an enolate ion followed by nucleophilic substitution. The choice of base employed is essential as it is the key factor in determining the reaction outcome.
The reaction involving bases like EtO− whose conjugate acid EtOH (pKa = 15.9) is stronger than the ketone (pKa = 19.2) results in an equilibrium mixture with higher ketone concentration. As a consequence,...
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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 higher...
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Polymer Classification: Crystallinity01:21

Polymer Classification: Crystallinity

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Unlike ionic or small covalent molecules, polymers do not form crystalline solids due to the diffusion limitations of their long-chain structures. However, polymers contain microscopic crystalline domains separated by amorphous domains.
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Alkyl Halides02:45

Alkyl Halides

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Structural Properties
Alkyl halides are halogen-substituted alkanes wherein one or more hydrogen atoms of an alkane is replaced by a halogen atom such as fluorine, chlorine, bromine, or iodine. The carbon atom in an alkyl halide is bonded to the halogen atom, which is sp3-hybridized and exhibits a tetrahedral shape.
Unlike alkyl halides, compounds in which a halogen atom is bonded to an sp2 -hybridized carbon atom of a carbon-carbon double bond (C=C) are called vinyl halides. Whereas aryl...
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Electron Transport Chains01:28

Electron Transport Chains

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The final stage of cellular respiration is oxidative phosphorylation that consists of two steps: the electron transport chain and chemiosmosis. The electron transport chain is a set of proteins found in the inner mitochondrial membrane in eukaryotic cells. Its primary function is to establish a proton gradient that can be used during chemiosmosis to produce ATP and generate electron carriers, such as NAD+ and FAD, that are used in glycolysis and the citric acid cycle.
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Base Excision Repair

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One of the common DNA damages is the chemical alteration of single bases by alkylation, oxidation, or deamination. The altered bases cause mispairing and strand breakage during replication. This type of damage causes minimal change to the DNA double helix structure and can be repaired by the base excision repair (BER) pathways. BER corrects damaged DNA sequences by removing the damaged base and restoring the original base sequence using the complementary strand as a template.
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Crystalline CO2 -Based Aliphatic Polycarbonates with Long Alkyl Chains.

Lena Kunze1, Jonas Wolfs1, Patrick Verkoyen1

  • 1Institute of Organic Chemistry, Johannes Gutenberg University of Mainz, Duesbergweg 10-14,, 55128, Mainz, Germany.

Macromolecular Rapid Communications
|October 16, 2018
PubMed
Summary

This study demonstrates the copolymerization of carbon dioxide (CO2) with dodecyl glycidyl ether and propylene oxide to create novel aliphatic polycarbonates. The resulting polymers exhibit tunable properties and high molecular weights, offering sustainable material solutions.

Keywords:
catalystscopolymerizationcrystallizationpolycarbonatesthermal properties

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Area of Science:

  • Polymer Chemistry
  • Materials Science
  • Sustainable Chemistry

Background:

  • Carbon dioxide (CO2) is an abundant, renewable carbon source with potential for chemical valorization.
  • Aliphatic polycarbonates can be synthesized via ring-opening polymerization of epoxides.
  • CO2 can be incorporated as a comonomer to create functional polycarbonate materials.

Purpose of the Study:

  • To synthesize novel aliphatic polycarbonates by copolymerizing CO2 with dodecyl glycidyl ether (DDGE) and propylene oxide (PO).
  • To investigate the effect of comonomer ratio on copolymer properties.
  • To characterize the molecular weight, thermal properties, and composition of the resulting copolymers.

Main Methods:

  • Catalytic ring-opening copolymerization of epoxides (DDGE and PO) with CO2.
  • Utilized a binary catalytic system: (R,R)-Co(salen)Cl/[PPN]Cl.
  • Characterization techniques included NMR, FT-IR spectroscopy, SEC, differential scanning calorimetry (DSC), and thermogravimetric analysis (TGA).

Main Results:

  • Successfully synthesized aliphatic poly(dodecyl glycidyl ether carbonate) and poly(propylene carbonate-co-dodecyl glycidyl ether carbonate) copolymers.
  • Achieved high molecular weights ranging from 11,400 to 37,900 g mol⁻¹ with low dispersities (1.37-1.61).
  • Obtained copolymers with tunable glass transition temperatures (Tg) down to -11 °C or melting temperatures (Tm) from 5 to 15 °C, and thermal decomposition above 200 °C.

Conclusions:

  • The catalytic system efficiently copolymerizes CO2 with DDGE and PO to produce high molecular weight aliphatic polycarbonates.
  • The comonomer ratio significantly influences the thermal properties (Tg, Tm) and molecular characteristics of the copolymers.
  • These findings highlight the potential of using CO2 as a sustainable building block for designing functional aliphatic polycarbonates.