Jump to main content
Jump to site search
Access to RSC content Close the message box

Continue to access RSC content when you are not at your institution. Follow our step-by-step guide.


Issue 30, 2017
Previous Article Next Article

Endo-/exo- and halogen-bonded complexes of conformationally rigid C-ethyl-2-bromoresorcinarene and aromatic N-oxides

Author affiliations

Abstract

The host–guest complexes of conformationally rigid C-ethyl-2-bromoresorcinarene with aromatic N-oxides were studied using single crystal X-ray crystallography. Unlike that of the conformationally more flexible C-ethyl-2-methylresorcinarene, the C-ethyl-2-bromoresorcinarene cavity forms endo-complexes only with the small pyridine-N-oxides, such as pyridine N-oxide, 2-methyl-, 3-methyl- and 4-methylpyrdine N-oxide, and quinoline N-oxide. The larger 2,4,6-trimethylpyridine, 4-phenylpyridine and isoquinoline N-oxide, and 4,4-bipyridine N,N′-dioxide and 1,3-bis(4-pyridyl)propane N,N′-dioxide do not fit into the host cavity. Instead endo-acetone complexes are formed. Remarkably, differing from the antigauche endo-complex with C-ethyl-2-methylresorcinarene, the flexible 1,3-bis(4-pyridyl)propane N,N′-dioxide guest forms an antianti exo-complex with C-ethyl-2-bromoresorcinarene. The endo- and exo-complexes of C-ethyl-2-bromoresorcinarene and studied N-oxides manifest C–O⋯Br, C–H⋯π and C–Br⋯π interactions.

Graphical abstract: Endo-/exo- and halogen-bonded complexes of conformationally rigid C-ethyl-2-bromoresorcinarene and aromatic N-oxides

Back to tab navigation

Supplementary files

Article information


Submitted
22 May 2017
Accepted
14 Jun 2017
First published
15 Jun 2017

CrystEngComm, 2017,19, 4312-4320
Article type
Paper

Endo-/exo- and halogen-bonded complexes of conformationally rigid C-ethyl-2-bromoresorcinarene and aromatic N-oxides

R. Puttreddy, N. K. Beyeh, R. H. A. Ras, J. F. Trant and K. Rissanen, CrystEngComm, 2017, 19, 4312
DOI: 10.1039/C7CE00975E

Social activity

Search articles by author

Spotlight

Advertisements