Co-crystals of an organic triselenocyanate with ditopic Lewis bases: recurrent chalcogen bond interactions motifs

Asia Marie S. Riel; Olivier Jeannin; Orion B. Berryman; Marc Fourmigué

doi:10.1107/S2052520618017778

Co-crystals of an organic triselenocyanate with ditopic Lewis bases: recurrent chalcogen bond interactions motifs

Asia Marie S. Riel
, Olivier Jeannin
, Orion B. Berryman
, Marc Fourmigué

Université de Rennes

Research output: Contribution to journal › Article › peer-review

15 Scopus citations

Abstract

Organic selenocyanates R–Se–CN can act as an amphoteric chalcogen bond (ChB) donor (through the Se atom) and acceptor (through the N atom lone pair). Co-crystallization of tri-substituted 1,3,5-tris(selenocyanatomethyl)-2,4,6-trimethylbenzene (1) is investigated with different ditopic Lewis bases acting as chalcogen bond (ChB) acceptors to investigate the outcome of the competition, as ChB acceptor, between the nitrogen lone pair of the SeCN group and other Lewis bases involving pyridinyl or carbonyl functions. In the presence of tetramethylpyrazine (TMP), benzoquinone (BQ) and para-dinitrobenzene (pDNB) as ditopic Lewis bases, a recurrent oligomeric motif stabilized by six ChB interactions is observed, involving six SeCN groups and the ChB acceptor sites of TMP, BQ and pDNB in the 2:1 adducts (1) ₂ ·TMP, (1) ₂ ·BQ and (1) ₂ ·pDNB.

Original language	English
Pages (from-to)	34-38
Number of pages	5
Journal	Acta Crystallographica Section B: Structural Science, Crystal Engineering and Materials
Volume	75
Issue number	1
DOIs	https://doi.org/10.1107/S2052520618017778
State	Published - Feb 1 2019

Keywords

chalcogen bond
sigma-hole interactions

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10.1107/S2052520618017778

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title = "Co-crystals of an organic triselenocyanate with ditopic Lewis bases: recurrent chalcogen bond interactions motifs",

abstract = " Organic selenocyanates R–Se–CN can act as an amphoteric chalcogen bond (ChB) donor (through the Se atom) and acceptor (through the N atom lone pair). Co-crystallization of tri-substituted 1,3,5-tris(selenocyanatomethyl)-2,4,6-trimethylbenzene (1) is investigated with different ditopic Lewis bases acting as chalcogen bond (ChB) acceptors to investigate the outcome of the competition, as ChB acceptor, between the nitrogen lone pair of the SeCN group and other Lewis bases involving pyridinyl or carbonyl functions. In the presence of tetramethylpyrazine (TMP), benzoquinone (BQ) and para-dinitrobenzene (pDNB) as ditopic Lewis bases, a recurrent oligomeric motif stabilized by six ChB interactions is observed, involving six SeCN groups and the ChB acceptor sites of TMP, BQ and pDNB in the 2:1 adducts (1) 2 ·TMP, (1) 2 ·BQ and (1) 2 ·pDNB.",

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author = "Riel, \{Asia Marie S.\} and Olivier Jeannin and Berryman, \{Orion B.\} and Marc Fourmigu{\'e}",

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doi = "10.1107/S2052520618017778",

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Co-crystals of an organic triselenocyanate with ditopic Lewis bases: recurrent chalcogen bond interactions motifs. / Riel, Asia Marie S.; Jeannin, Olivier; Berryman, Orion B. et al.
In: Acta Crystallographica Section B: Structural Science, Crystal Engineering and Materials, Vol. 75, No. 1, 01.02.2019, p. 34-38.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

T1 - Co-crystals of an organic triselenocyanate with ditopic Lewis bases

T2 - recurrent chalcogen bond interactions motifs

AU - Riel, Asia Marie S.

AU - Jeannin, Olivier

AU - Berryman, Orion B.

AU - Fourmigué, Marc

N1 - Publisher Copyright: © International Union of Crystallography, 2019

PY - 2019/2/1

Y1 - 2019/2/1

N2 - Organic selenocyanates R–Se–CN can act as an amphoteric chalcogen bond (ChB) donor (through the Se atom) and acceptor (through the N atom lone pair). Co-crystallization of tri-substituted 1,3,5-tris(selenocyanatomethyl)-2,4,6-trimethylbenzene (1) is investigated with different ditopic Lewis bases acting as chalcogen bond (ChB) acceptors to investigate the outcome of the competition, as ChB acceptor, between the nitrogen lone pair of the SeCN group and other Lewis bases involving pyridinyl or carbonyl functions. In the presence of tetramethylpyrazine (TMP), benzoquinone (BQ) and para-dinitrobenzene (pDNB) as ditopic Lewis bases, a recurrent oligomeric motif stabilized by six ChB interactions is observed, involving six SeCN groups and the ChB acceptor sites of TMP, BQ and pDNB in the 2:1 adducts (1) 2 ·TMP, (1) 2 ·BQ and (1) 2 ·pDNB.

AB - Organic selenocyanates R–Se–CN can act as an amphoteric chalcogen bond (ChB) donor (through the Se atom) and acceptor (through the N atom lone pair). Co-crystallization of tri-substituted 1,3,5-tris(selenocyanatomethyl)-2,4,6-trimethylbenzene (1) is investigated with different ditopic Lewis bases acting as chalcogen bond (ChB) acceptors to investigate the outcome of the competition, as ChB acceptor, between the nitrogen lone pair of the SeCN group and other Lewis bases involving pyridinyl or carbonyl functions. In the presence of tetramethylpyrazine (TMP), benzoquinone (BQ) and para-dinitrobenzene (pDNB) as ditopic Lewis bases, a recurrent oligomeric motif stabilized by six ChB interactions is observed, involving six SeCN groups and the ChB acceptor sites of TMP, BQ and pDNB in the 2:1 adducts (1) 2 ·TMP, (1) 2 ·BQ and (1) 2 ·pDNB.

KW - chalcogen bond

KW - sigma-hole interactions

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DO - 10.1107/S2052520618017778

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JO - Acta Crystallographica Section B: Structural Science, Crystal Engineering and Materials

JF - Acta Crystallographica Section B: Structural Science, Crystal Engineering and Materials

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ER -

Co-crystals of an organic triselenocyanate with ditopic Lewis bases: recurrent chalcogen bond interactions motifs

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