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ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3

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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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Enolate ions are formed by the acid–base reaction of a carbonyl compound with a base. This leads to deprotonation of the α hydrogen atom, leading to a resonance-stabilized enolate ion where one of the contributing structures is an oxyanion, which imparts additional stability. Therefore, the proton on the α carbon is more acidic in nature than that of other sp3-hybridized C–H bonds but less acidic than those in O–H bonds where the negative charge in the conjugate...
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Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

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The rate of acid-catalyzed hydration of alkenes depends on the alkene's structure, as the presence of alkyl substituents at the double bond can significantly influence the rate.
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Regioselectivity and Stereochemistry of Hydroboration02:36

Regioselectivity and Stereochemistry of Hydroboration

8.5K
A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn...
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Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule02:17

Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule

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If a set of reactants can yield multiple constitutional isomers, but one of the isomers is obtained as the major product, the reaction is said to be regioselective. In such reactions, bond formation or breaking is favored at one reaction site over others.
The hydrohalogenation of an unsymmetrical alkene can yield two haloalkane products, depending on which vinylic carbon takes up the halogen. However, one product usually predominates, where hydrogen adds to the vinylic carbon bearing the...
14.8K
ortho–para-Directing Deactivators: Halogens01:24

ortho–para-Directing Deactivators: Halogens

6.0K
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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Hydroxy Groups Enhance [2]Rotaxane Anion Binding Selectivity.

Rosemary J Goodwin1, Andrew Docker2, Hugo I MacDermott-Opeskin1

  • 1Research School of Chemistry, Australian National University, Canberra, ACT, Australia.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|March 16, 2022
PubMed
Summary
This summary is machine-generated.

Researchers developed novel [2]rotaxanes for selective chloride anion binding. The rotaxane with phenol donors showed enhanced selectivity due to optimized binding pocket interactions.

Keywords:
anionshydroxy groupsmolecular dynamicspreorganisationrotaxanes

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Area of Science:

  • Supramolecular Chemistry
  • Organic Synthesis
  • Anion Recognition

Background:

  • Rotaxanes are mechanically interlocked molecules with potential applications in molecular recognition.
  • Designing selective anion receptors remains a significant challenge in supramolecular chemistry.
  • Hydrogen bonding interactions play a crucial role in host-guest complexation.

Purpose of the Study:

  • To synthesize and characterize novel [2]rotaxanes with three-dimensional binding cavities.
  • To investigate the anion binding properties of these rotaxanes, particularly their selectivity for chloride.
  • To elucidate the structural basis for enhanced anion selectivity through experimental and computational methods.

Main Methods:

  • Synthesis of pyridinium bis(amide) based [2]rotaxanes.
  • Anion binding studies using competitive solvent mixtures (CDCl3:CD3OD).
  • X-ray crystallography for structural determination of host-guest complexes.
  • Computational semi-empirical simulations to analyze binding interactions.

Main Results:

  • Two [2]rotaxanes with interlocked binding cavities were successfully synthesized.
  • One rotaxane derivative demonstrated significantly higher selectivity for chloride anions compared to a control.
  • X-ray structures confirmed chloride encapsulation within the binding cavity.
  • Computational studies revealed secondary interactions contributing to a preorganized binding pocket.

Conclusions:

  • The synthesized [2]rotaxanes represent a promising class of receptors for selective anion binding.
  • The presence of phenol donors and secondary interactions enhances chloride selectivity.
  • Further studies can explore modifications for tailored anion recognition applications.