Cyclopent[b,c]acenaphthylene; an Elusive Isomer of Pyracylene with the Ring Currents of an Annelated Pentalene

R.W.A. Havenith, L.W. Jenneskens, P.W. Fowler, E. Steiner

Research output: Contribution to journalArticleAcademicpeer-review

Abstract

Ab initio ipsocentric current–density mapping techniques are used to visualise the current density induced by a perpendicular magnetic field in the still unknown cyclopent[b,c]acenaphthylene (1). The π system divides into distinct, but contiguous, paratropic and diatropic regions, both supporting extended ring currents, the two currents running together along the pentagon–hexagon border. On the usual magnetic definition, cyclopent[b,c]acenaphthylene (1) is therefore part aromatic and part antiaromatic. Orbital analysis attributes the ring–current magnetic response of 1 to its eight most energetic π electrons. It is concluded that cyclopent[b,c]acenaphthylene (1) constitutes an ‘annelated pentalene’. This is supported by the computed 1H NMR chemical shifts of 1; they are all positioned upfield with respect to naphthalene (3).
Original languageEnglish
Pages (from-to)2033-2039
Number of pages7
JournalPhysical Chemistry Chemical Physics
Volume2004
Issue number9
DOIs
Publication statusPublished - 2004

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