A new hydrogen bonding motif based on 10-hydroxy-10,9-borazarophenanthrene

Kenneth D.M. Harris, Benson M. Kariuki, Cristos Lambropoulos, Douglas Philp, James M.A. Robinson

Research output: Contribution to journalArticlepeer-review

21 Scopus citations

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 baron followed by loss of water to form the corresponding anhydride. This reactivity is rationalised in terms of the electronic structure of the borazarophenanthrene system.

Original languageEnglish (US)
Pages (from-to)8599-8612
Number of pages14
JournalTetrahedron
Volume53
Issue number25
DOIs
StatePublished - Jun 23 1997

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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