Molecular Recognition by Chalcogen Bond: Selective Chargetransfer Crystal Formation of Dimethylnaphthalene with Selenadiazolotetracyanonaphthoquinodimethane - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue European Journal of Organic Chemistry Année : 2021

Molecular Recognition by Chalcogen Bond: Selective Chargetransfer Crystal Formation of Dimethylnaphthalene with Selenadiazolotetracyanonaphthoquinodimethane

Résumé

The title nonplanar electron acceptor (1) fused with a selenadiazole ring selectively forms a crystalline charge-transfer complex (CT crystal) with 2,6-dimethylnaphthalene (2,6-DMN). On the other hand, the sulfur analogue (2) has less recognition ability and forms CT crystals with both 2,6-and 2,7-DMN. X-ray analyses of 1, 2, and their CT crystals revealed that the Se ••• N chalcogen bond (ChB) in 1 is strong enough to determine the crystal packing with the formation of a cavity suitable for 2,6-DMN. On the contrary, ChB through S ••• N contact in 2 competes with other weak interactions such as a C-H ••• N hydrogen bond. The stronger ChB involving Se is the key for 1 to separate 2,6-DMN (>97 wt%) from a complex isomer mixture containing ca. 10 wt% each of 2,6and 2,7-DMN by a simple, efficient and straightforward mixingfiltration-heating process.

Domaines

Chimie
Fichier principal
Vignette du fichier
10.1002ejoc.202001554.pdf (954.4 Ko) Télécharger le fichier
Origine : Fichiers produits par l'(les) auteur(s)

Dates et versions

hal-03114533 , version 1 (19-01-2021)

Identifiants

Citer

Yusuke Ishigaki, Kota Asai, Henri-Pierre Jacquot de Rouville, Takuya Shimajiri, Valérie Heitz, et al.. Molecular Recognition by Chalcogen Bond: Selective Chargetransfer Crystal Formation of Dimethylnaphthalene with Selenadiazolotetracyanonaphthoquinodimethane. European Journal of Organic Chemistry, In press, ⟨10.1002/ejoc.202001554⟩. ⟨hal-03114533⟩

Collections

SITE-ALSACE
63 Consultations
116 Téléchargements

Altmetric

Partager

Gmail Facebook X LinkedIn More