Conformational changes in Cmethyl-resorcinarene pyridine N -oxide inclusion complexes in the solid state

Rakesh Puttreddy, Ngong Kodiah Beyeh, Kari Rissanen*

*Corresponding author for this work

Research output: Contribution to journalArticleScientificpeer-review

9 Citations (Scopus)
120 Downloads (Pure)

Abstract

Aromatic N-oxides interact with Cmethyl-resorcinarene resulting in marked changes in the conformation of the host resorcinarene. In the solid state, 2- and 3-methylpyridine N-oxides form pseudo-capsular 2 : 2 endo host-guest complexes with Cmethyl-resorcinarene stabilized by C-H⋯π interactions. The Cmethyl-resorcinarene·2-methylpyridine N-oxide complex has a C4v crown conformation, while the Cmethyl-resorcinarene·3-methylpyridine N-oxide complex has a slightly open C2v boat conformation. On the contrary, other para-substituted and benzo-fused pyridine N-oxides form only exo complexes with Cmethyl-resorcinarene. In the exo complexes, the asymmetry of the guest, conformational flexibility and preferred inter-host hydrogen bonding of Cmethyl-resorcinarenes exclude endo complexation. All the exo complexes form robust 1-D hydrogen bonded chains between the host hydroxyl groups assisted by the guest N-O groups, resulting in a C2v boat conformation.

Original languageEnglish
Pages (from-to)4971-4976
Number of pages6
JournalCrystEngComm
Volume18
Issue number26
DOIs
Publication statusPublished - Feb 2016
MoE publication typeA1 Journal article-refereed

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  • Datasets

    CCDC 1450587: Experimental Crystal Structure Determination

    Beyeh, N. (Creator), Puttreddy, R. (Contributor) & Rissanen, K. (Contributor), Cambridge Crystallographic Data Centre , 1 Jan 2016

    Dataset

    CCDC 1450585: Experimental Crystal Structure Determination

    Beyeh, N. (Creator), Puttreddy, R. (Contributor) & Rissanen, K. (Contributor), Cambridge Crystallographic Data Centre , 1 Jan 2016

    Dataset

    CCDC 1450586: Experimental Crystal Structure Determination

    Beyeh, N. (Creator), Puttreddy, R. (Contributor) & Rissanen, K. (Contributor), Cambridge Crystallographic Data Centre , 1 Jan 2016

    Dataset

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