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Related Concept Videos

Directing Effect of Substituents: ortho–para-Directing Groups01:14

Directing Effect of Substituents: ortho–para-Directing Groups

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Ortho–para directors are substituent groups attached to the benzene ring and direct the addition of an electrophile to the positions ortho or para to the substituent. All electron-donating groups are considered ortho–para directors. They donate electrons to the ring and make the ring more electron-rich. The ring is therefore susceptible to the addition of electrophiles. Substituents such as amino, hydroxy, or alkoxy, containing lone pairs on the atom adjacent to the ring, donate...
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Halogens are ortho–para directors. They are more electronegative than carbon. Therefore, as ring substituents, they can withdraw electrons through the inductive effect and deactivate the aromatic ring towards electrophilic substitution. Halogens also have an electron-donating resonance effect on the ring, which influences the orientation of the incoming electrophile. If an electrophile attacks at the ortho or the para position, the halogen donates electrons and stabilizes the intermediate...
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ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

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All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...
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Metallic Solids

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Metallic solids such as crystals of copper, aluminum, and iron are formed by metal atoms. The structure of metallic crystals is often described as a uniform distribution of atomic nuclei within a “sea” of delocalized electrons. The atoms within such a metallic solid are held together by a unique force known as metallic bonding that gives rise to many useful and varied bulk properties.
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A phase diagram combines plots of pressure versus temperature for the liquid-gas, solid-liquid, and solid-gas phase-transition equilibria of a substance. These diagrams indicate the physical states that exist under specific conditions of pressure and temperature and also provide the pressure dependence of the phase-transition temperatures (melting points, sublimation points, boiling points). Regions or areas labeled solid, liquid, and gas represent single phases, while lines or curves represent...
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Structures of Solids

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Solids in which the atoms, ions, or molecules are arranged in a definite repeating pattern are known as crystalline solids. Metals and ionic compounds typically form ordered, crystalline solids. A crystalline solid has a precise melting temperature because each atom or molecule of the same type is held in place with the same forces or energy. Amorphous solids or non-crystalline solids (or, sometimes, glasses) which lack an ordered internal structure and are randomly arranged. Substances that...
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Directed ortho-Lithiation on Solid Phase.

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Researchers developed a novel resin-bound 1-hydroxyimidazole synthesis. This method efficiently produces various 2-substituted 1-hydroxyimidazoles, offering a versatile route for chemical synthesis.

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry
  • Medicinal Chemistry

Background:

  • 1-hydroxyimidazoles are important heterocyclic compounds with diverse applications.
  • Traditional synthesis methods for substituted imidazoles can be complex and low-yielding.
  • Developing efficient and versatile synthetic routes is crucial for accessing novel imidazole derivatives.

Purpose of the Study:

  • To develop a robust and efficient method for synthesizing 2-substituted 1-hydroxyimidazoles.
  • To utilize a solid-phase synthesis approach for improved purification and scalability.
  • To explore the scope of functionalization at the C-2 position of the 1-hydroxyimidazole core.

Main Methods:

  • Alkylation of sodium 1-hydroxyimidazole with chloromethyl polystyrene to create a resin-bound intermediate.
  • Lithiation at the C-2 position using n-butyllithium.
  • Reaction of the lithiated intermediate with various carbon, halogen, and sulfur electrophiles.
  • Detachment of the product from the solid support using trifluoroacetic acid.

Main Results:

  • Successful synthesis of resin-bound 1-hydroxyimidazole.
  • Efficient lithiation at the C-2 position of the immobilized intermediate.
  • Broad scope of C-2 functionalization demonstrated with diverse electrophiles.
  • High yields (52-93%) of 2-substituted 1-hydroxyimidazoles after cleavage from the resin.

Conclusions:

  • The developed solid-phase synthesis provides a versatile and efficient route to 2-substituted 1-hydroxyimidazoles.
  • This method simplifies purification and offers potential for library synthesis.
  • The approach is valuable for generating diverse imidazole derivatives for various applications.