Dilithioplumbole: A lead-bearing aromatic cyclopentadienyl analog

Masaichi Saito; Masafumi Sakaguchi; Tomoyuki Tajima; Kazuya Ishimura; Shigeru Nagase; Masahiko Hada

doi:10.1126/science.1183648

Dilithioplumbole: A lead-bearing aromatic cyclopentadienyl analog

Masaichi Saito, Masafumi Sakaguchi, Tomoyuki Tajima, Kazuya Ishimura, Shigeru Nagase, Masahiko Hada

Research output: Contribution to journal › Article › peer-review

89 Citations (Scopus)

Abstract

Although the concept of aromaticity has long played an important role in carbon chemistry, it has been unclear how applicable the stabilizing framework is to the heaviest elements. Here we report the synthesis of dilithiotetraphenylplumbole by reduction of hexaphenylplumbole. X-ray crystallography revealed a planar structure with no alternation of carbon-carbon bond lengths in the five-membered ring core. Nuclear magnetic resonance spectra and relativistic theoretical calculations show considerable aromatic character in the molecule, thus extending aromaticity to carbon's heaviest congener.

Original language	English
Pages (from-to)	339-342
Number of pages	4
Journal	Science
Volume	328
Issue number	5976
DOIs	https://doi.org/10.1126/science.1183648
Publication status	Published - Apr 16 2010
Externally published	Yes

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abstract = "Although the concept of aromaticity has long played an important role in carbon chemistry, it has been unclear how applicable the stabilizing framework is to the heaviest elements. Here we report the synthesis of dilithiotetraphenylplumbole by reduction of hexaphenylplumbole. X-ray crystallography revealed a planar structure with no alternation of carbon-carbon bond lengths in the five-membered ring core. Nuclear magnetic resonance spectra and relativistic theoretical calculations show considerable aromatic character in the molecule, thus extending aromaticity to carbon's heaviest congener.",

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AU - Sakaguchi, Masafumi

AU - Tajima, Tomoyuki

AU - Ishimura, Kazuya

AU - Nagase, Shigeru

AU - Hada, Masahiko

PY - 2010/4/16

Y1 - 2010/4/16

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AB - Although the concept of aromaticity has long played an important role in carbon chemistry, it has been unclear how applicable the stabilizing framework is to the heaviest elements. Here we report the synthesis of dilithiotetraphenylplumbole by reduction of hexaphenylplumbole. X-ray crystallography revealed a planar structure with no alternation of carbon-carbon bond lengths in the five-membered ring core. Nuclear magnetic resonance spectra and relativistic theoretical calculations show considerable aromatic character in the molecule, thus extending aromaticity to carbon's heaviest congener.

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Dilithioplumbole: A lead-bearing aromatic cyclopentadienyl analog

Abstract

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