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

✍ Scribed by Stephen M. Aucott; Heather L. Milton; Stuart D. Robertson; Alexandra M. Z. Slawin; J. Derek Woollins

• Publisher: John Wiley and Sons
• Year: 2004
• Tongue: English
• Weight: 494 KB
• Volume: 15
• Category: Article
• ISSN: 1042-7163
• DOI: 10.1002/hc.20055

✦ Synopsis

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 1‐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.

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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. © 2004 Wiley Periodicals, Inc. Heteroatom Chem 15:530–542, 2004; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20055