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Zeitschrift für Naturforschung B

A Journal of Chemical Sciences

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Alkylaluminum, -gallium, -magnesium, and -zinc monophenolates with bulky substituents

Clint E. Price
  • Department of Chemical and Biomedical Science and Engineering, Florida Institute of Technology, 150 West University Boulevard, Melbourne, FL 32901, USA
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/ Ana B. Dantas
  • Department of Chemical and Biomedical Science and Engineering, Florida Institute of Technology, 150 West University Boulevard, Melbourne, FL 32901, USA
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/ Douglas R. Powell
  • Department of Chemistry and Biochemistry, University of Oklahoma, 101 Stephenson Parkway, Norman, OK 73019-5251, USA
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/ Rudolf J. Wehmschulte
  • Corresponding author
  • Department of Chemical and Biomedical Science and Engineering, Florida Institute of Technology, 150 West University Boulevard, Melbourne, FL 32901, USA
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Published Online: 2018-09-24 | DOI: https://doi.org/10.1515/znb-2018-0176

Abstract

The bulky phenols 2,6-Ad2C6H3OH (Ad=adamantyl), A, (2,6-Ph2CH)2-4-Me-C6H2OH, B, and (2,6-Tol2CH)2-4-iPr-C6H2OH, C, react with one equivalent of Et3M (M=Al, Ga), Bu2Mg and Et2Zn to afford well-defined mono-phenolate complexes (ArOMRn)m. The aluminum and gallium phenolates derived from the very bulky phenol A are likely monomeric in the solid state. The other compounds are dimeric with bridging phenolates. Crystal structures of compounds with phenols B and C display the dimeric M2O2 cores of the phenolates and illustrate some deviations for the magnesium and zinc compounds. The former possesses stabilizing Mg···C contacts with one of the flanking arene groups of the phenolate substituent, and the latter may be viewed as an intermediate between a symmetric dimer and two monomers. All compounds were characterized by 1H and 13C NMR spectroscopy, and their solution spectra are in agreement with the crystal structure data.

This article offers supplementary material which is provided at the end of the article.

Keywords: metal alkyl; metal···π contacts; phenolate; X-ray crystal structure

Dedicated to: Professor Werner Uhl on the occasion of his 65th birthday.

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About the article

Received: 2018-08-21

Accepted: 2018-09-04

Published Online: 2018-09-24


Citation Information: Zeitschrift für Naturforschung B, 20180176, ISSN (Online) 1865-7117, ISSN (Print) 0932-0776, DOI: https://doi.org/10.1515/znb-2018-0176.

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