Syn and Anti Isomers of [2.2]Paracyclonapthane

TitleSyn and Anti Isomers of [2.2]Paracyclonapthane
Publication TypeJournal Article
Year of Publication1995
AuthorsA.V. Fratini, M.L. Chabinyc, T.J. Perko, and W.W. Adams
JournalACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS
Volume51
Pagination904-908
Date PublishedMAY 15
ISSN0108-2701
Abstract

The structures of the anti (1) and syn (2) isomers of [2.2]paracyclonaphthane, C24H20, can be understood in terms of molecules composed of four segments, two naphthalene rings and two ethylene groups bridging the naphthalene rings. Distortions from ideal geometries are described and attributed primarily to intramolecular effects. Several observations have been made: the bridged portion of the naphthalene ring is deformed into a boat shape in both (1) and (2); much of the pi-pi repulsion is taken up by bending angles alpha and beta; the naphthalene rings are parallel to each other in (1), but are nonparallel in (2); one naphthalene ring in (2) is twisted relative to the other, indicating a mode of strain reduction which is unique to this molecule, and the C-C distances and valency angles in the ethylene bridges are larger than normal values.

DOI10.1107/S0108270194009959