Chalcogen Bond versus Weak Hydrogen Bond: Changing Contributions in Determining the Crystal Packing of [1,2,5]-Chalcogenadiazole-Fused Tetracyanonaphthoquinodimethanes

Chalcogen Bond versus Weak Hydrogen Bond: Changing Contributions in Determining the Crystal Packing of [1,2,5]-Chalcogenadiazole-Fused Tetracyanonaphthoquinodimethanes

Abstract The crystal structures of a series of tetracyanonaphthoquinodimethanes fused with a selenadiazole or thiadiazole ring revealed that their molecular packing is determined mainly by two intermolecular interactions: chalcogen bond (ChB) and weak hydrogen bond (WHB). ChB between Se and a cyano...

Full description

Bibliographic Details
Main Authors: Yusuke Ishigaki, Kota Asai, Takuya Shimajiri, Tomoyuki Akutagawa, Takanori Fukushima, Takanori Suzuki
Format: Article
Language:English
Published: Georg Thieme Verlag 2021-04-01
Series:Organic Materials
Subjects:
crystal engineering
weak hydrogen bonds
chalcogen bonds
chalcogenadiazoles
tetracyanoquinodimethanes
x-ray analysis
Online Access:http://www.thieme-connect.de/DOI/DOI?10.1055/s-0041-1725046
id doaj-04b86d3693de4e3f8f77cca4f99619cc
record_format Article
spelling doaj-04b86d3693de4e3f8f77cca4f99619cc2021-04-06T05:15:54ZengGeorg Thieme VerlagOrganic Materials2625-18252021-04-01030209009610.1055/s-0041-1725046Chalcogen Bond versus Weak Hydrogen Bond: Changing Contributions in Determining the Crystal Packing of [1,2,5]-Chalcogenadiazole-Fused TetracyanonaphthoquinodimethanesYusuke Ishigaki0Kota Asai1Takuya Shimajiri2Tomoyuki Akutagawa3Takanori Fukushima4Takanori Suzuki5Department of Chemistry, Faculty of Science, Hokkaido University, Sapporo, Hokkaido 060-0810, Japan.Department of Chemistry, Faculty of Science, Hokkaido University, Sapporo, Hokkaido 060-0810, Japan.Department of Chemistry, Faculty of Science, Hokkaido University, Sapporo, Hokkaido 060-0810, Japan.Institute of Multidisciplinary Research for Advanced Materials, Tohoku University, Sendai, Miyagi 980-8577, JapanLaboratory for Chemistry and Life Science, Institute of Innovative Research, Tokyo Institute of Technology, Yokohama 226-8503, JapanDepartment of Chemistry, Faculty of Science, Hokkaido University, Sapporo, Hokkaido 060-0810, Japan.Abstract The crystal structures of a series of tetracyanonaphthoquinodimethanes fused with a selenadiazole or thiadiazole ring revealed that their molecular packing is determined mainly by two intermolecular interactions: chalcogen bond (ChB) and weak hydrogen bond (WHB). ChB between Se and a cyano group dictates the packing of selenadiazole derivatives, whereas the S-based ChB is much weaker and competes with WHB in thiadiazole analogues. This difference can be explained by different electrostatic potentials as revealed by density functional theory calculations. A proper molecular design that weakens WHB can change the contribution of ChB in determining the crystal packing of thiadiazole derivatives.http://www.thieme-connect.de/DOI/DOI?10.1055/s-0041-1725046crystal engineeringweak hydrogen bondschalcogen bondschalcogenadiazolestetracyanoquinodimethanesx-ray analysis
collection DOAJ
language English
format Article
sources DOAJ
author Yusuke Ishigaki
Kota Asai
Takuya Shimajiri
Tomoyuki Akutagawa
Takanori Fukushima
Takanori Suzuki
spellingShingle Yusuke Ishigaki
Kota Asai
Takuya Shimajiri
Tomoyuki Akutagawa
Takanori Fukushima
Takanori Suzuki
Chalcogen Bond versus Weak Hydrogen Bond: Changing Contributions in Determining the Crystal Packing of [1,2,5]-Chalcogenadiazole-Fused Tetracyanonaphthoquinodimethanes
Organic Materials
crystal engineering
weak hydrogen bonds
chalcogen bonds
chalcogenadiazoles
tetracyanoquinodimethanes
x-ray analysis
author_facet Yusuke Ishigaki
Kota Asai
Takuya Shimajiri
Tomoyuki Akutagawa
Takanori Fukushima
Takanori Suzuki
author_sort Yusuke Ishigaki
title Chalcogen Bond versus Weak Hydrogen Bond: Changing Contributions in Determining the Crystal Packing of [1,2,5]-Chalcogenadiazole-Fused Tetracyanonaphthoquinodimethanes
title_short Chalcogen Bond versus Weak Hydrogen Bond: Changing Contributions in Determining the Crystal Packing of [1,2,5]-Chalcogenadiazole-Fused Tetracyanonaphthoquinodimethanes
title_full Chalcogen Bond versus Weak Hydrogen Bond: Changing Contributions in Determining the Crystal Packing of [1,2,5]-Chalcogenadiazole-Fused Tetracyanonaphthoquinodimethanes
title_fullStr Chalcogen Bond versus Weak Hydrogen Bond: Changing Contributions in Determining the Crystal Packing of [1,2,5]-Chalcogenadiazole-Fused Tetracyanonaphthoquinodimethanes
title_full_unstemmed Chalcogen Bond versus Weak Hydrogen Bond: Changing Contributions in Determining the Crystal Packing of [1,2,5]-Chalcogenadiazole-Fused Tetracyanonaphthoquinodimethanes
title_sort chalcogen bond versus weak hydrogen bond: changing contributions in determining the crystal packing of [1,2,5]-chalcogenadiazole-fused tetracyanonaphthoquinodimethanes
publisher Georg Thieme Verlag
series Organic Materials
issn 2625-1825
publishDate 2021-04-01
description Abstract The crystal structures of a series of tetracyanonaphthoquinodimethanes fused with a selenadiazole or thiadiazole ring revealed that their molecular packing is determined mainly by two intermolecular interactions: chalcogen bond (ChB) and weak hydrogen bond (WHB). ChB between Se and a cyano group dictates the packing of selenadiazole derivatives, whereas the S-based ChB is much weaker and competes with WHB in thiadiazole analogues. This difference can be explained by different electrostatic potentials as revealed by density functional theory calculations. A proper molecular design that weakens WHB can change the contribution of ChB in determining the crystal packing of thiadiazole derivatives.
topic crystal engineering
weak hydrogen bonds
chalcogen bonds
chalcogenadiazoles
tetracyanoquinodimethanes
x-ray analysis
url http://www.thieme-connect.de/DOI/DOI?10.1055/s-0041-1725046
work_keys_str_mv AT yusukeishigaki chalcogenbondversusweakhydrogenbondchangingcontributionsindeterminingthecrystalpackingof125chalcogenadiazolefusedtetracyanonaphthoquinodimethanes
AT kotaasai chalcogenbondversusweakhydrogenbondchangingcontributionsindeterminingthecrystalpackingof125chalcogenadiazolefusedtetracyanonaphthoquinodimethanes
AT takuyashimajiri chalcogenbondversusweakhydrogenbondchangingcontributionsindeterminingthecrystalpackingof125chalcogenadiazolefusedtetracyanonaphthoquinodimethanes
AT tomoyukiakutagawa chalcogenbondversusweakhydrogenbondchangingcontributionsindeterminingthecrystalpackingof125chalcogenadiazolefusedtetracyanonaphthoquinodimethanes
AT takanorifukushima chalcogenbondversusweakhydrogenbondchangingcontributionsindeterminingthecrystalpackingof125chalcogenadiazolefusedtetracyanonaphthoquinodimethanes
AT takanorisuzuki chalcogenbondversusweakhydrogenbondchangingcontributionsindeterminingthecrystalpackingof125chalcogenadiazolefusedtetracyanonaphthoquinodimethanes
_version_ 1721538512467001344

Similar Items