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Towards Norcorrin: Hydrogenation Chemistry and the Heterodimerization of Nickel(II) Norcorrole
Author(s) -
Liu Bin,
Li Xiaofang,
Stępień Marcin,
Chmielewski Piotr J.
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201500736
Subject(s) - cyclic voltammetry , chemistry , nickel , raney nickel , chloranil , redox , yield (engineering) , spectroscopy , spectrophotometry , nuclear magnetic resonance spectroscopy , medicinal chemistry , inorganic chemistry , photochemistry , nuclear chemistry , electrochemistry , organic chemistry , catalysis , electrode , materials science , physics , quantum mechanics , chromatography , metallurgy
5,14‐Dimesitylnorcorrolatonickel(II) was hydrogenated under mild conditions (room temperature, 1 atm H 2 , THF solution, 5 min.) in the presence of Raney nickel to yield nonaromatic derivatives that were isolated and characterized by NMR spectroscopy, UV/Vis spectrophotometry, HRMS, cyclic voltammetry, and X‐ray diffraction analysis. The major hydrogenation product, 1,2,3,7,8,9‐hexahydronorcorrolatonickel(II), underwent dimerization in the presence of p ‐chloranil to give a nonsymmetrically linked 2,3′‐bis(norcorrole) system that can adopt eight different oxidation states over a redox potential window of 3 V and has a HOMO–LUMO gap of 0.92 V.
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