Crystal structures and molecular modeling of 1,8 chalcogenide-substituted naphthalenes

S M Aucott, H L Milton, S D Robertson, A M Z Slawin, J D Woollins

Research output: Contribution to journalArticle

32 Citations (Scopus)

Abstract

The molecular structures of naphtho[1,8-cd][1,2]dithiole, naphtho[1,8-cd][1,2]diselenole, naphtho[1,8-cd][1,2]ditellurole, naphtho[1,8-cd][1,2]dithiole I-oxide, naphtho[1,8-cd][1,2]dithiole 1,1-dioxide, and naphtho[1,8-cd][1,2]dithiole 1,1,2-trioxideand naphtho[1,8-cd][1,2]dithiole 1,1,2,2-tetroxide are compared. The E-E distance varies, broadly reflecting the degree of distortion imposed by the rigid naphthalene backbone as well as the degree of oxidation at sulfur. The naphthalene backbone imposes shortening of E-E bond lengths when E = S and Se compared to Ph-E-E-Ph systems but is itself subject to distortion as a consequence of the steric bulk of the E atoms. 

Original languageEnglish
Pages (from-to)530-542
Number of pages13
JournalHeteroatom Chemistry
Volume15
Issue number7
DOIs
Publication statusPublished - 2004

Keywords

  • proton sponge
  • salts
  • analog
  • molecular modeling
  • naphthalenes

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