A New Hydrogen Bonding Motif Based on 10-Hydroxy-10,9-Borazarophenanthrene

Douglas Philp, KDM Harris, BM Kariuki, C Lambropoulos, other 1

Research output: Contribution to journalArticlepeer-review

25 Citations (Scopus)

Abstract

The rational design of a system which mimics the molecular recognition properties of carboxylic acids but displays markedly different reactivity is presented. 10-Hydroxy-10,9-borazarophenanthrene is predicted by both structural analogy with carboxylic acids and ab initio calculations to form cyclic hydrogen bonded homodimers and its crystal structure demonstrates that this expectation is fulfilled. In solution, however, the reactivity of 10-hydroxy-10,9-borazarophenanthrene is markedly different from that of carboxylic acids - reacting with itself under certain conditions by nucleophilic addition at boron followed by loss of water to form the corresponding anhydride. This reactivity is rationalised in terms of the electronic structure of the borazarophenanthrene system. (C) 1997 Elsevier Science Ltd.

Original languageEnglish
Pages (from-to)8599-8612
Number of pages14
JournalTetrahedron
Volume53
Publication statusPublished - 23 Jun 1997

Keywords

  • COMPLEMENTARY MOLECULAR-COMPONENTS
  • SOLID-STATE
  • RECOGNITION
  • CRYSTALS
  • ACID
  • AGGREGATION
  • NETWORKS
  • GEOMETRY

Fingerprint

Dive into the research topics of 'A New Hydrogen Bonding Motif Based on 10-Hydroxy-10,9-Borazarophenanthrene'. Together they form a unique fingerprint.

Cite this