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Cation–anion CH⋯O− interactions in the metal-free phenolate, tetra-n-butylammonium phenol-phenolate

Authors :
Richard Goddard
Manfred T. Reetz
H. Martin Herzog
Source :
Tetrahedron. 58:7847-7850
Publication Year :
2002
Publisher :
Elsevier BV, 2002.

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) A). A short contact between one α-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.

Details

ISSN :
00404020
Volume :
58
Database :
OpenAIRE
Journal :
Tetrahedron
Accession number :
edsair.doi...........9fa57bdd392942b5e8fa7307c7ca5fb1