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Cation-anion CH...O¯ interactions in the metal-free phenolate, tetra-n-butylammonium phenol-phenolate

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Goddard,  R.
Service Department Lehmann (EMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society;
Service Department Lehmann (EMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society;
Service Department Lehmann (EMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Herzog,  H. M.
Research Department Reetz, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Reetz,  M. T.
Research Department Reetz, Max-Planck-Institut für Kohlenforschung, Max Planck Society;
Research Department Reetz, Max-Planck-Institut für Kohlenforschung, Max Planck Society;
Research Department Reetz, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Goddard, R., Herzog, H. M., & Reetz, M. T. (2002). Cation-anion CH..O¯ interactions in the metal-free phenolate, tetra-n-butylammonium phenol-phenolate. Tetrahedron, 58(39), 7847-7850. doi:10.1016/S0040-4020(02)00900-6.


Cite as: http://hdl.handle.net/11858/00-001M-0000-000F-9997-7
Abstract
Deprotonation of phenol by tetra-n-butylammonium hydroxide and subsequent removal of water by P2O5 results in quantitative formation of tetra-n-butylammonium phenol-phenolate. The compound crystallizes as an ion pair, with the solute phenol molecule intimately attached to the phenolate anion by an O- H...O- hydrogen bond (O...O 2.471(5) Angstrom). A short contact between one alpha-C atom of the tetra-n-butylammonium cation and the phenolate O atom indicates that the ion pair interaction is strengthened by an additional C-H...O- hydrogen- bond, despite the attached phenol. (C) 2002 Elsevier Science Ltd. All rights reserved.