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Updated: Jul 16, 2026

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
Published on: April 1, 2013
Molecular and electronic structure of 1,8-peribridged naphthalenes
Igor Novak1, Leslie J Harrison, Wei Li
1Charles Sturt University, POB 883, Orange NSW 2800, Australia. inovak@csu.edu.au
Abstract:
The crystal and molecular structure of 1,8-thianaphthalene has been determined and compared with other single-atom peribridged naphthalenes (SAPN). The measured CSC angle is 73.06 degrees, which is the smallest bridging angle yet recorded for a SAPN derivative. The ab initio calculations using G3(MP2)//B3LYP method were performed for peribridged naphthalenes in order to determine how the strain of the four-membered ring is influenced by the type of bridge linking 1,8 positions. The electronic structure of 1,8-thia- and 1,8-sulfonenaphthalenes has been studied by UV photoelectron spectroscopy. We have tried to identify and distinguish the strain effect on the electronic structure of the naphthalene moiety.
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