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[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

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The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
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meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H01:13

meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H

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All meta-directing substituents are deactivating groups. These substituents withdraw electrons from the aromatic ring, making the ring less reactive toward electrophilic substitution. For example, the nitration of nitrobenzene is 100,000 times slower than that of benzene because of the deactivating effect of the nitro group. The first step in an electrophilic aromatic substitution is the addition of an electrophile to form a resonance-stabilized carbocation. The energy diagrams for...
6.6K
2° Amines to N-Nitrosamines: Reaction with NaNO201:20

2° Amines to N-Nitrosamines: Reaction with NaNO2

5.4K
Secondary amines react with nitrous acid to form N-nitrosamines, as depicted in Figure 1. Nitrous acid, a weak and unstable acid, is formed in situ from an aqueous solution of sodium nitrite and strong acids, such as hydrochloric acid or sulfuric acid, in cold conditions. In the presence of an acid, the nitrous acid gets protonated. The subsequent loss of water results in the formation of the electrophile known as nitrosonium ion.
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Coordination Number and Geometry02:57

Coordination Number and Geometry

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For transition metal complexes, the coordination number determines the geometry around the central metal ion. Table 1 compares coordination numbers to molecular geometry. The most common structures of the complexes in coordination compounds are octahedral, tetrahedral, and square planar.
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SN2 Reaction: Kinetics02:14

SN2 Reaction: Kinetics

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Kinetic Studies and Significance
In a chemical reaction, a relationship exists between the concentration of reactants and the rate at which the reaction proceeds. The study to measure this relationship is known as the kinetics of a chemical reaction. Kinetic studies are used to deduce the rate law of a chemical reaction, which provides information about the species involved during the transition state of the rate-determining step. Thus, kinetic studies help to derive the mechanism of a...
10.2K
Lattice Centering and Coordination Number02:33

Lattice Centering and Coordination Number

11.4K
The structure of a crystalline solid, whether a metal or not, is best described by considering its simplest repeating unit, which is referred to as its unit cell. The unit cell consists of lattice points that represent the locations of atoms or ions. The entire structure then consists of this unit cell repeating in three dimensions. The three different types of unit cells present in the cubic lattice are illustrated in Figure 1.
Types of Unit Cells
Imagine taking a large number of identical...
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Preparation of Highly Porous Coordination Polymer Coatings on Macroporous Polymer Monoliths for Enhanced Enrichment of Phosphopeptides
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A Multistimulus Responsive Porous Coordination Polymer: Temperature-Mediated Control of Solid-State [2+2]

Isabella E Claassens1, Leonard J Barbour1, Delia A Haynes1

  • 1Department of Chemistry and Polymer Science , Stellenbosch University , P. Bag X1, Matieland , 7602 Stellenbosch , South Africa.

Journal of the American Chemical Society
|July 17, 2019
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Researchers controlled photochemical [2+2] cycloaddition within porous coordination polymers (PCPs) by temperature. This temperature-induced phase transition alters ligand conformation, selectively yielding different isomeric products. This highlights PCPs

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Area of Science:

  • Materials Science
  • Photochemistry
  • Supramolecular Chemistry

Background:

  • Porous coordination polymers (PCPs) offer tunable environments for chemical reactions.
  • Photochemical [2+2] cycloaddition is a key reaction for forming cyclobutane rings.
  • Controlling reaction selectivity in confined spaces remains a challenge.

Purpose of the Study:

  • To investigate the selective synthesis of isomeric products via photochemical [2+2] cycloaddition within a PCP.
  • To explore the influence of temperature on the reaction outcome.
  • To understand the role of ligand flexibility in PCP responsiveness.

Main Methods:

  • Synthesis of a porous coordination polymer (PCP) incorporating 1,4-bis[2-(4-pyridyl)ethenyl]-benzene ligands.
  • Photochemical [2+2] cycloaddition reactions conducted at different temperatures.
  • Analysis of reaction products using spectroscopic and crystallographic techniques.
  • Investigation of temperature-induced phase transitions in the PCP.

Main Results:

  • Selective formation of two different isomeric cycloaddition products was achieved.
  • The specific isomer obtained was directly dependent on the irradiation temperature.
  • A rare temperature-induced phase transition was observed, altering ligand conformation.
  • This conformational change dictated the regioselectivity of the cycloaddition.

Conclusions:

  • The flexibility of ligands in PCPs enables multistimulus responsiveness.
  • Temperature can be used as an external stimulus to control photochemical reactions within PCPs.
  • This work demonstrates a novel approach for selective synthesis of isomeric compounds using smart materials.