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

Aucott, S M and Milton, H L and Robertson, S D and Slawin, A M Z and Woollins, J D (2004) Crystal structures and molecular modeling of 1,8 chalcogenide-substituted naphthalenes. Heteroatom Chemistry, 15 (7). pp. 530-542. ISSN 1042-7163

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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.