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Endo-/Exo- and Halogen Bonded Complexes of Conformationally Rigid Cethyl-2-bromoresorcinarene and aromatic N-oxides

Abstract

The host-guest complexes of conformationally rigid Cethyl-2-bromoresorcinarene with aromatic N-oxides were studied using single crystal X-ray crystallography. Unlike the conformationally more flexible Cethyl-2-methylresorcinarene, the Cethyl-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 anti-gauche exo-complex with C-ethyl-2-methylresorcinarene), the flexible 1,3-bis(4-pyridyl)propane N,N'-dioxide guest forms an anti-anti exo-complex with C-ethyl-2-bromoresorcinarene. The endo- and exo-complexes of C-ethyl-2-bromoresorcinarene and studied N-oxides manifest C-OBr, C-H and C-Br interactions.

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Publication details

The article was received on 22 May 2017, accepted on 14 Jun 2017 and first published on 15 Jun 2017


Article type: Paper
DOI: 10.1039/C7CE00975E
Citation: CrystEngComm, 2017, Accepted Manuscript
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    Endo-/Exo- and Halogen Bonded Complexes of Conformationally Rigid Cethyl-2-bromoresorcinarene and aromatic N-oxides

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

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