Halogen Bonding in Solution

10 Chapter 10Figure 10.1 Biomolecular origami. (a) DNA origami in which a single strand o...Figure 10.2 Examples of halogenated nucleic acids and amino acids. On the le...Figure 10.3 Comparing the hydrogen bond (H‐bond) and the halogen bond (X‐bon...Figure 10.4 Electrostatic model for and effects on halogen bonds. (a) The σ‐...Figure 10.5 Relationships between hydrogen bonds and halogen bonds. (a) Comp...Figure 10.6 The H‐bond enhanced X‐bond (HBeXB). QM calculated electrostatic ...Figure 10.7 Intertwined, intercalated parallel helices of d(AC BrUCGGA BrUGA)....Figure 10.8 Effect of an X‐bond on the transition from duplex to four‐strand...Figure 10.9 Comparing the octamer structure of the unmodified to the hexamer...Figure 10.10 Assembly of d(G BrCGAGAGC). The interface is shown that hold two...Figure 10.11 Competition between H‐bonds and X‐bonds to control the isomer c...Figure 10.12 Comparison of X‐bonding energies for halogen substituents (X = ...Figure 10.13 Orthogonal X‐bonds from diiodotetrafluorobenzene to H‐bonded N ‐...Figure 10.14 X‐bond stabilization of β‐conformation in a cyclic peptide. NMR...Figure 10.15 Peptide foldamers incorporating eight halogenated α/L‐sulfono‐γ...Figure 10.16 Effect of halogenated amino acids on the structure and stabilit...Figure 10.17 Structure of meta ‐halotyrosine at position 18 at the active sit...Figure 10.18 Predicted X‐bonded nucleic acid base pairs and quartets. The le...

11 Chapter 11Scheme 11.1 (a) Schematic illustration of halogen and chalcogen bonds (R 1is...Scheme 11.2 (a) ChB donor abilities of Se and Te.(b) Effect of electron ...Scheme 11.3 (a) Positive charge‐assisted chalcogen bonding in 9– 14.(b) N...Scheme 11.4 Reaction of 18with Na 2Ch 2.Scheme 11.5 Intramolecular Te ⋯N types of chalcogen bonding in organote...Scheme 11.6 Intramolecular Se ⋯N types of chalcogen bonding in asymmetr...Scheme 11.7 Se ⋯O chalcogen bonding in asymmetric reaction of diselenid...Scheme 11.8 Role of intramolecular Se ⋯S interactions in asymmetric add...Scheme 11.9 (a) Michael addition of 5‐methoxy‐1 H ‐indole to ( E )‐(2‐nitrovinyl...Scheme 11.10 (a) Chalcogen bond‐assisted solvolysis of (bromomethylene)diben...Scheme 11.11 Chalcogen bond‐promoted CCl bond activation in 1‐chloroisochro...Scheme 11.12 (a) One‐pot synthesis of seven‐membered N ‐heterocycles. (b) ChB...Scheme 11.13 Intramolecular chalcogen bond‐supported intermediates in the en...Scheme 11.14 Anion binding modes of ChB donor receptors.Scheme 11.15 Negative charge‐assisted chalcogen bonds in mono‐ and bidentate...Scheme 11.16 Positive charge‐assisted chalcogen bonding in the detection of ...Scheme 11.17 Acyclic HaB‐ and ChB‐based receptors for the recognition of I −...Scheme 11.18 ChB‐promoted anion transport.

1 Cover Page

2 Title Page Halogen Bonding in Solution Edited by Stefan Huber

3 Copyright Editor Stefan Huber Ruhr‐Universität Bochum Organische Chemie I Universitätsstr. 150 NC 4/171 44801 Bochum Germany Cover Images © Olga Moonlight/Shutterstock © andrew hall/Alamy Stock Photo All books published by Wiley‐VCH are carefully produced. Nevertheless, authors, editors, and publisher do not warrant the information contained in these books, including this book, to be free of errors. Readers are advised to keep in mind that statements, data, illustrations, procedural details or other items may inadvertently be inaccurate. Library of Congress Card No.: applied for British Library Cataloguing‐in‐Publication Data A catalogue record for this book is available from the British Library. Bibliographic information published by the Deutsche Nationalbibliothek The Deutsche Nationalbibliothek lists this publication in the Deutsche Nationalbibliografie; detailed bibliographic data are available on the Internet at < http://dnb.d-nb.de >. © 2021 WILEY‐VCH GmbH, Boschstr. 12, 69469 Weinheim, Germany All rights reserved (including those of translation into other languages). No part of this book may be reproduced in any form – by photoprinting, microfilm, or any other means – nor transmitted or translated into a machine language without written permission from the publishers. Registered names, trademarks, etc. used in this book, even when not specifically marked as such, are not to be considered unprotected by law. Print ISBN: 978‐3‐527‐34731‐5 ePDF ISBN: 978‐3‐527‐82572‐1 ePub ISBN: 978‐3‐527‐82574‐5 oBook ISBN: 978‐3‐527‐82573‐8

4 Preface

5 Table of Contents

6 Begin Reading

7 Index

8 WILEY END USER LICENSE AGREEMENT

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