[C-H···O] interactions as a control element in supramolecular complexes: Experimental and theoretical evaluation of receptor affinities for the binding of bipyridinium-based guests by catenated hosts

Journal of the American Chemical Society

Volumn 121, Issue 7, 1999, Pages 1479-1487

  Houk, K N ^a   Menzer, Stephan ^c   Newton, Simon P ^b   Raymo, Françisco M ^a,b   Stoddart, J Fraser ^a,b   Williams, David J ^c  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b UNIVERSITY OF BIRMINGHAM   (United Kingdom)

^c IMPERIAL COLLEGE LONDON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE; COMPLEX FORMATION; CRYSTAL STRUCTURE; HYDROGEN BOND; MOLECULAR INTERACTION; RECEPTOR AFFINITY; SYNTHESIS;

EID: 0033599295     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja982748b     Document Type: Article

References (55)

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37. The mean interplanar separations between both the "inside" and "alongside" 1,5-dioxynaphthalene residues and the bipyridinium unit are in each case 3.5 Å. There are [C-H⋯O] hydrogen bonds (i) between one of the hydrogen atoms in the α-positions with respect to the nitrogen atoms on the bipyridinium units and a central polyether oxygen atom ([C⋯O], 3.38 Å; [H⋯O], 2.46 Å; [C-H⋯O], 161°) and (ii) between one of the methylene groups of the tetracationic cyclophane and the adjacent oxygen atom of the same polyether linkage ([C⋯O], 3.30 Å: [H⋯O], 2.45 Å; [C-H⋯O], 148°). Additionally, there are edge-to-face [C-H⋯π] interactions involving the hydrogen atoms in the 4- and 8-positions of the "inside" 1,5-dioxynaphthalene residues and the proximal p-phenylene rings of the tetracationic cyclophane (respectively: [H⋯π], 2.73 and 2.82 Å; [C-H⋯π], 145 and 141°).
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40. The mean interplanar separations between both the "inside" and "alongside" 1,5-dioxynaphthalene residues and the bipyridinium unit are 3.33 and 3.35 Å. There are [C-H⋯O] hydrogen bonds (i) between diametrically opposite pairs of hydrogen atoms located in the α-positions with respect to the nitrogen atoms on the bipyridinium units and the oxygen atoms in the proximal polyether linkages (respectivley: [C⋯O]. 3.26, 3.30, and 3.23 Å; [H⋯O], 2.43, 2.44, and 2.45 Å; [C-H⋯O], 145, 148, and 138°) and (ii) between one of the methylene groups of the tetracationic cylophane and one of the oxygen atoms in one of the polyether linkages ([C⋯O], 3.12 Å; [H⋯O], 2.39 Å; [C-H⋯O], 133°). Additionally, there are two edge-to-face [C-H⋯π] interactions involving the "inside" 1,5-dioxynaphthalene residues and the proximal p-phenylene rings of the tetracationic cyclophane ([H⋯π], 2.72 and 2.76 Å; [C-H⋯π], 148 and 145°).
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47. No significant differences were observed in the values of the interaction energies when these were calculated with the inclusion of chloride counterions.
48. A similar effect was observed experimentally in a series of related pseudorotaxanes incorporating bipyridinium and 1,4-dioxybenzene recognition sites: (a) Anelli, P. L.; Ashton, P. R.; Ballardini, R.; Balzani, V.; Delgado, M.; Gandolfi, M. T.; Goodnow, T. T.; Kaifer, A. E.; Philp, D.; Pietraszkiewicz, M.; Prodi, L.; Reddington, M. V.; Slawin, A. M. Z.; Spencer, N.; Stoddart, J. F.; Vicent, C.; Williams, D. J. J. Am. Chem. Soc. 1992, 114, 193-218.
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