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Chalcogen bonding interactions in organic selenocyanates: from cooperativity to chelation

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Abstract

Intermolecular chalcogen bonding interactions are identified in crystalline organic selenocyanates where a linear Se⋯N[triple bond, length as m-dash]C interaction takes place, leading to the recurrent formation of chain-like motifs ⋯Se(R)–CN⋯Se(R)–CN⋯, stabilized by cooperativity. Analysis of 15 reported structures of such selenocyanates is complemented by the structural determinations of three other novel polytopic selenocyanates, namely 1,3,5-tris(selenocyanatomethyl)benzene (1a), 1,3,5-tris(selenocyanatomethyl)-2,4,6-trimethylbenzene (1b) and 1,2,4,5-tetrakis(selenocyanatomethyl)benzene (2). While the recurrent chain-like motifs with short and linear Se⋯N contacts are indeed observed in the pure compounds, solvates with DMF and AcOEt also demonstrate that the nitrile N atom can be easily displaced from the chalcogen bond by stronger Lewis bases such as carbonyl oxygen atoms, leading in the case of (2)·(DMF)2 to a chelating motif where two neighboring CH2–SeCN groups link to the same oxygen atom through Se⋯O interactions.

Graphical abstract: Chalcogen bonding interactions in organic selenocyanates: from cooperativity to chelation

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Publication details

The article was received on 31 Jan 2018, accepted on 04 Mar 2018 and first published on 06 Mar 2018


Article type: Paper
DOI: 10.1039/C8NJ00554K
Citation: New J. Chem., 2018, Advance Article
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    Chalcogen bonding interactions in organic selenocyanates: from cooperativity to chelation

    O. Jeannin, H. Huynh, A. M. S. Riel and M. Fourmigué, New J. Chem., 2018, Advance Article , DOI: 10.1039/C8NJ00554K

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