Simultaneous electrophile-nucleophile Cl ⋯π interactions stabilizing solid state inclusions: A new tool for supramolecular crystal engineering

Ingeborg Csöregh, Edwin Weber, Thomas Hens, Mátyás Czugler

Research output: Contribution to journalArticle

32 Citations (Scopus)

Abstract

The crystalline inclusions of the host compound trans-11,12-bis[bis(p-chlorophenyl)hydroxymethyl]-9,10-ethanoanthracene, with guests such as pentan-2-ol [1·pentan-2-ol (1:1), la], 1,4-dioxane [1-1,4-dioxane (2:5), 1b] and o-xylene [1·o-xylene (1:2), lc] were shown by X-ray analysis to have host matrices mainly determined by directional 'electrophile-nucleophile pairing' interactions, involving a chloro substituent and the adjacent aryl n electrons of a neighbouring molecule. The observed shorter Cl⋯centroid distances in la-c are between 3.33 and 3.75 A. On the other hand, the versatility of host-guest interactions due to the different proton donor-acceptor abilities and polarities of the guests yielded various packing relations with different symmetries and conformations of the host hydroxy functions. Although compounds la and lb contain H-bonded 1·pentanol and 1·dioxane aggregates, respectively, the realized packing arrangements seem to be a compromise between close packing on the one hand and hydrogen bonding on the other. Compound lc is a lattice-type inclusion in which the o-xylene guests are trapped in tunnels formed by the bulky host molecules.

Original languageEnglish
Pages (from-to)2733-2739
Number of pages7
JournalJournal of the Chemical Society. Perkin Transactions 2
Volume1996
Issue number12
DOIs
Publication statusPublished - Jan 1 1996

ASJC Scopus subject areas

  • Chemistry(all)

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