NDLI: Overcrowded naphthologs of mono-bridged tetraarylethylenes: analogs of bistricyclic aromatic enes

Content Provider	Springer Nature Link
Author	Assadi, Naela Pogodin, Sergey Cohen, Shmuel Levy, Amalia Agranat, Israel
Copyright Year	2009
Abstract	The naphthalogous mono-bridged tetraarylethylenes 9,9′-di-(1-naphthylmethylene)-9H-fluorene (5) and 9,9′-di-(1-naphthylmethylene)-9H-xanthene (6), analogs of bifluorenylidene (1) and bixanthenylidene (2), have been synthesized and their molecular and crystal structures have been determined. Ene 5 has been prepared by two alternative synthetic routes. The molecular structures of 5 and 6 show that each of these enes has very small twist around the central double bond, but the two naphthalene rings in both 5 and 6 are highly twisted. According to the NMR study, 5 and 6 in solution adopt conformations which are similar to those found by X-ray crystal structure analysis. The notable upfield shifts of H$^{1}$ and H$^{8}$ (6.11 and 6.83 ppm, respectively) and H$^{2}$ and H$^{7}$ (6.70 and 6.44 ppm, respectively) in 5 and 6 are due to the shielding caused by the nearly orthogonally twisted naphthalene rings. The B3LYP/6-31G(d) calculations of 5, 6, and their 2-naphthyl and phenyl analogs have been performed. In the 1-naphthyl series, the more efficient conjugation between the naphthyl substituents and the central C=C and the overcrowding due to the peri-hydrogen atoms lead to higher twists of the naphthyl groups and to lower twists of the central C=C. In the 2-naphthyl series, the opposite effects are noted.
Starting Page	541
Ending Page	556
Page Count	16
File Format	PDF
ISSN	10400400
Journal	Structural Chemistry
Volume Number	20
Issue Number	4
e-ISSN	15729001
Language	English
Publisher	Springer US
Publisher Date	2009-05-13
Publisher Place	Boston
Access Restriction	One Nation One Subscription (ONOS)
Subject Keyword	Mono-bridged tetraarylethylenes Diazo-thione coupling Crystal structures NMR DFT Theoretical and Computational Chemistry Physical Chemistry Computer Applications in Chemistry
Content Type	Text
Resource Type	Article
Subject	Physical and Theoretical Chemistry Condensed Matter Physics

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