Bent aromatic rings in naphthalene derivatives

Peter R. Ashton*, George R. Brown, Alan J. Foubister, Diane R. Smith, Neil Spencer, J. Fraser Stoddart, David J. Williams

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

7 Scopus citations

Abstract

X-Ray crystallography and dynamic 1H NMR spectroscopy have revealed that 1,4,5,8-tetramethyl-, 1-bromomethyl-4,5,8-trimethyl-, and 1,8-bis(bromomethyl)-4,5-dimethyl-2,3,6,7-tetrabromonaphthalene - 3, 4, and 5, respectively - have severely distorted naphthalene nuclei in the solid state that also correspond to the gross conformations that occupy appreciable (ΔG‡∼16 kcal mol-1) energy wells in the solution state.

Original languageEnglish (US)
Pages (from-to)8333-8336
Number of pages4
JournalTetrahedron Letters
Volume34
Issue number51
DOIs
StatePublished - Dec 17 1993

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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