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Synthesis and structure of 1,3,5-tris(diorganohydroxysilyl)benzenes. Novel building blocks in supramolecular silanol chemistry

Beckmann, Jens, Duthie, Andrew, Reeske, Gregor and Schurmann, Markus 2004, Synthesis and structure of 1,3,5-tris(diorganohydroxysilyl)benzenes. Novel building blocks in supramolecular silanol chemistry, Organometallics, vol. 23, no. 20, pp. 4630-4635, doi: 10.1021/om049620p.

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Title Synthesis and structure of 1,3,5-tris(diorganohydroxysilyl)benzenes. Novel building blocks in supramolecular silanol chemistry
Author(s) Beckmann, Jens
Duthie, AndrewORCID iD for Duthie, Andrew orcid.org/0000-0002-1103-325X
Reeske, Gregor
Schurmann, Markus
Journal name Organometallics
Volume number 23
Issue number 20
Start page 4630
End page 4635
Publisher American Chemical Society
Place of publication Washington D.C., Wash.
Publication date 2004-08-25
ISSN 0276-7333
1520-6041
Summary The 1,3,5-tris(diorganohydroxysilyl)benzenes 1,3,5-(HOR2Si)3C6H3 (TMSB, R = Me; TPSB, R = Ph) have been prepared and fully characterized by X-ray crystallography. The crystal structure of TMSB features pairwise connected layers, in which the molecules are involved in interlayer hydrogen bonding. The supramolecular hydrogen bond motif may be described as a 12-membered ring that adopts a chair conformation. TPSB forms an equimolar inclusion complex with water, which is associated via hydrogen bonding and apparently fills a void in the crystal packing. In this case, the supramolecular hydrogen bond motif may be described as an eight-membered ring. Two of the water molecules are also associated, giving rise to a water dimer entrapped in the silanol matrix. Besides the hydrogen bonds, the crystal structure of the TPSB·H2O complex reveals intra- and intermolecular C-H··· π stacking of most of the phenyl groups. Electrospray mass spectrometry shows that TPSB undergoes supramolecular complex formation with a variety of N-donors such as 4-(dimethylamino)pyridine, N,N,N',N'-tetramethylethylenediamine, imidazole, 2-(dimethylamino)pyridine, and 2,2'-dipyridylamine.

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Language eng
DOI 10.1021/om049620p
Field of Research 039904 Organometallic Chemistry
Socio Economic Objective 970103 Expanding Knowledge in the Chemical Sciences
HERDC Research category C1 Refereed article in a scholarly journal
Copyright notice ©2004, American Chemical Society
Persistent URL http://hdl.handle.net/10536/DRO/DU:30002721

Document type: Journal Article
Collections: Faculty of Science, Engineering and Built Environment
School of Biological and Chemical Sciences
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