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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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Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.
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Computational design of pH-switchable control agents for nitroxide mediated polymerization.

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Novel nitroxides with acid-base groups act as pH-switchable agents for room temperature nitroxide-mediated polymerization (NMP). These compounds are inert when neutral but effective when deprotonated, enabling controlled polymerization of styrene.

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Area of Science:

  • Polymer Chemistry
  • Computational Chemistry
  • Organic Chemistry

Background:

  • Nitroxide-mediated polymerization (NMP) is a controlled radical polymerization technique.
  • Developing efficient and tunable control agents for NMP is crucial for polymer synthesis.
  • pH-responsive materials offer advanced functionalities in various applications.

Purpose of the Study:

  • To evaluate known and novel nitroxides with acid-base functionalities as pH-switchable control agents for room temperature NMP.
  • To identify nitroxide structures suitable for controlled styrene polymerization under specific pH conditions.
  • To explore the potential of these agents in diverse polymerization applications.

Main Methods:

  • Accurate quantum chemistry calculations were employed to assess nitroxide properties.
  • G3(MP2,CC)(+)//M06-2X/6-31+G(d) calculations were performed.
  • UAKS-CPCM/M06-2X/6-31+G(d) solvation corrections were applied to simulate aqueous environments.

Main Results:

  • Several novel nitroxides were predicted to be effective for room temperature NMP when deprotonated (negatively charged).
  • These effective nitroxides include an α-ethyl analogue of 3-carboxy-PROXYL and modified TIPNO derivatives.
  • Other evaluated species, like 3,4-dicarboxy-PROXYL and SG1 derivatives, showed pH-switching suitability around 60 °C.

Conclusions:

  • The study identifies promising pH-switchable nitroxide control agents for room temperature NMP.
  • Deprotonation of nitroxides with acid-base groups activates their control capability for styrene polymerization.
  • These findings offer new avenues for designing responsive polymers and advanced materials.