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Radical reactions can occur either intermolecularly or intramolecularly. In an intermolecular radical reaction, a nucleophilic radical adds to an electrophilic alkene or vice versa. In such reactions, the radical and generally the alkene, which is also called the radical trap, are two different molecules. Additionally, for such intermolecular reactions to occur, the radical trap must be active, present in an excess concentration, and the radical starting material must have a weak...
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Nucleophilic substitution in aromatic compounds is feasible in substrates bearing strong electron-withdrawing substituents positioned ortho or para to the leaving group. The reaction proceeds via two steps: the addition of the nucleophile and the elimination of the leaving group.
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Introduction
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Exploring short intramolecular interactions in alkylaromatic substrates.

Alberto Baggioli1, Carlo A Cavallotti1, Antonino Famulari1

  • 1Dipartimento di Chimica, Materiali e Ingegneria Chimica "G. Natta", Politecnico di Milano, via Mancinelli 7, I-20131 Milano, Italy. alberto.baggioli@polimi.it.

Physical Chemistry Chemical Physics : PCCP
|October 27, 2016
PubMed
Summary
This summary is machine-generated.

Alkyl-aromatic interactions in macromolecules influence material properties. Computational analysis reveals twisted conformations can be more stable than extended ones, offering new design guidelines.

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Area of Science:

  • Macromolecular science and materials chemistry.
  • Computational chemistry and molecular modeling.

Background:

  • Aliphatic chains on aromatic groups are key structural motifs in diverse macromolecules, influencing their physical properties through folding and packing.
  • Understanding intramolecular interactions within these units is crucial for predicting macromolecular behavior and material performance.

Purpose of the Study:

  • To investigate the conformational preferences of alkylaromatic units, focusing on intramolecular interactions between aliphatic X-H bonds and aromatic rings.
  • To provide guidelines for predicting the most stable conformations of these building blocks.

Main Methods:

  • Utilized a set of 23 model compounds with intramolecular interactions between aliphatic X-H (X = C, N, O, S) and aromatic systems.
  • Employed advanced computational techniques, including CCSD(T) calculations and Non-Covalent Interaction (NCI) topological analysis.

Main Results:

  • Revealed complex networks of dispersive and steric interactions governing molecular conformation.
  • Observed that twisted conformational isomers can exhibit higher energetic stability compared to extended side-chain conformations, contrary to initial expectations.
  • Investigated the influence of vicinal covalent effects and heteroatoms on conformational stability.

Conclusions:

  • Developed a comprehensive set of guidelines to predict the most stable conformations for alkylaromatic building blocks.
  • Findings have implications for organic electronics, photovoltaics, and understanding protein/peptide folding preferences.