A Robust Supramolecular Heterosynthon Assembled by a Hydrogen Bond and a Chalcogen Bond
The 1:1 and 2:1 cocrystals of isophthalic acid and 2,1,3-benzoselenadiazole have been successfully synthesized and resolved; the noncovalent interactions in the crystal structures have been studied in detail by quantum chemical calculations. In both of the crystal structures, isophthalic acid and 2,...
Guardado en:
| Autores principales: | , , , , , , |
|---|---|
| Formato: | article |
| Lenguaje: | EN |
| Publicado: |
MDPI AG
2021
|
| Materias: | |
| Acceso en línea: | https://doaj.org/article/53c5dae82b9f4967ab9869238db84d87 |
| Etiquetas: |
Agregar Etiqueta
Sin Etiquetas, Sea el primero en etiquetar este registro!
|
| id |
oai:doaj.org-article:53c5dae82b9f4967ab9869238db84d87 |
|---|---|
| record_format |
dspace |
| spelling |
oai:doaj.org-article:53c5dae82b9f4967ab9869238db84d872021-11-25T17:18:04ZA Robust Supramolecular Heterosynthon Assembled by a Hydrogen Bond and a Chalcogen Bond10.3390/cryst111113092073-4352https://doaj.org/article/53c5dae82b9f4967ab9869238db84d872021-10-01T00:00:00Zhttps://www.mdpi.com/2073-4352/11/11/1309https://doaj.org/toc/2073-4352The 1:1 and 2:1 cocrystals of isophthalic acid and 2,1,3-benzoselenadiazole have been successfully synthesized and resolved; the noncovalent interactions in the crystal structures have been studied in detail by quantum chemical calculations. In both of the crystal structures, isophthalic acid and 2,1,3-benzoselenadiazole are bound together by a cyclic supramolecular heterosynthon assembled by an O–H···N hydrogen bond and a N–Se···O chalcogen bond. The crystal structures of the 1:1 and 2:1 cocrystals of isophthalic acid and 2,1,3-benzoselenadiazole and the crystal structure of pure isophthalic acid are very similar, which indicates that the [COOH]···[Se−N] cyclic heterosynthon can be an effective alternative to the strong [COOH]<sub>2</sub> cyclic homosynthon. The quantum theory of atoms in molecules further recognizes the existence of the hydrogen bond and chalcogen bond. The results of quantum chemical calculations show that the strengths of the π···π stacking interactions in the 1:1 cocrystals of isophthalic acid and 2,1,3-benzoselenadiazole are almost the same as those in the 2:1 cocrystals of isophthalic acid and 2,1,3-benzoselenadiazole, and the strengths of the [COOH]···[Se−N] cyclic heterosynthons (about 9.00 kcal/mol) are less than the strengths of the much stronger [COOH]<sub>2</sub> cyclic homosynthons (14.00 kcal/mol). These calculated results are in good agreement with those experimentally observed, demonstrating that, although not as strong as the [COOH]<sub>2</sub> cyclic homosynthon, the [COOH]···[Se−N] cyclic heterosynthon can also play a key role in the crystal growth and design.Shaobin MiaoYunfan ZhangLinjie ShanMingyuan XuJian-Ge WangYu ZhangWeizhou WangMDPI AGarticlesupramolecular synthonO–H···N hydrogen bondN–Se···O chalcogen bondπ···π stacking interactionquantum chemical calculationCrystallographyQD901-999ENCrystals, Vol 11, Iss 1309, p 1309 (2021) |
| institution |
DOAJ |
| collection |
DOAJ |
| language |
EN |
| topic |
supramolecular synthon O–H···N hydrogen bond N–Se···O chalcogen bond π···π stacking interaction quantum chemical calculation Crystallography QD901-999 |
| spellingShingle |
supramolecular synthon O–H···N hydrogen bond N–Se···O chalcogen bond π···π stacking interaction quantum chemical calculation Crystallography QD901-999 Shaobin Miao Yunfan Zhang Linjie Shan Mingyuan Xu Jian-Ge Wang Yu Zhang Weizhou Wang A Robust Supramolecular Heterosynthon Assembled by a Hydrogen Bond and a Chalcogen Bond |
| description |
The 1:1 and 2:1 cocrystals of isophthalic acid and 2,1,3-benzoselenadiazole have been successfully synthesized and resolved; the noncovalent interactions in the crystal structures have been studied in detail by quantum chemical calculations. In both of the crystal structures, isophthalic acid and 2,1,3-benzoselenadiazole are bound together by a cyclic supramolecular heterosynthon assembled by an O–H···N hydrogen bond and a N–Se···O chalcogen bond. The crystal structures of the 1:1 and 2:1 cocrystals of isophthalic acid and 2,1,3-benzoselenadiazole and the crystal structure of pure isophthalic acid are very similar, which indicates that the [COOH]···[Se−N] cyclic heterosynthon can be an effective alternative to the strong [COOH]<sub>2</sub> cyclic homosynthon. The quantum theory of atoms in molecules further recognizes the existence of the hydrogen bond and chalcogen bond. The results of quantum chemical calculations show that the strengths of the π···π stacking interactions in the 1:1 cocrystals of isophthalic acid and 2,1,3-benzoselenadiazole are almost the same as those in the 2:1 cocrystals of isophthalic acid and 2,1,3-benzoselenadiazole, and the strengths of the [COOH]···[Se−N] cyclic heterosynthons (about 9.00 kcal/mol) are less than the strengths of the much stronger [COOH]<sub>2</sub> cyclic homosynthons (14.00 kcal/mol). These calculated results are in good agreement with those experimentally observed, demonstrating that, although not as strong as the [COOH]<sub>2</sub> cyclic homosynthon, the [COOH]···[Se−N] cyclic heterosynthon can also play a key role in the crystal growth and design. |
| format |
article |
| author |
Shaobin Miao Yunfan Zhang Linjie Shan Mingyuan Xu Jian-Ge Wang Yu Zhang Weizhou Wang |
| author_facet |
Shaobin Miao Yunfan Zhang Linjie Shan Mingyuan Xu Jian-Ge Wang Yu Zhang Weizhou Wang |
| author_sort |
Shaobin Miao |
| title |
A Robust Supramolecular Heterosynthon Assembled by a Hydrogen Bond and a Chalcogen Bond |
| title_short |
A Robust Supramolecular Heterosynthon Assembled by a Hydrogen Bond and a Chalcogen Bond |
| title_full |
A Robust Supramolecular Heterosynthon Assembled by a Hydrogen Bond and a Chalcogen Bond |
| title_fullStr |
A Robust Supramolecular Heterosynthon Assembled by a Hydrogen Bond and a Chalcogen Bond |
| title_full_unstemmed |
A Robust Supramolecular Heterosynthon Assembled by a Hydrogen Bond and a Chalcogen Bond |
| title_sort |
robust supramolecular heterosynthon assembled by a hydrogen bond and a chalcogen bond |
| publisher |
MDPI AG |
| publishDate |
2021 |
| url |
https://doaj.org/article/53c5dae82b9f4967ab9869238db84d87 |
| work_keys_str_mv |
AT shaobinmiao arobustsupramolecularheterosynthonassembledbyahydrogenbondandachalcogenbond AT yunfanzhang arobustsupramolecularheterosynthonassembledbyahydrogenbondandachalcogenbond AT linjieshan arobustsupramolecularheterosynthonassembledbyahydrogenbondandachalcogenbond AT mingyuanxu arobustsupramolecularheterosynthonassembledbyahydrogenbondandachalcogenbond AT jiangewang arobustsupramolecularheterosynthonassembledbyahydrogenbondandachalcogenbond AT yuzhang arobustsupramolecularheterosynthonassembledbyahydrogenbondandachalcogenbond AT weizhouwang arobustsupramolecularheterosynthonassembledbyahydrogenbondandachalcogenbond AT shaobinmiao robustsupramolecularheterosynthonassembledbyahydrogenbondandachalcogenbond AT yunfanzhang robustsupramolecularheterosynthonassembledbyahydrogenbondandachalcogenbond AT linjieshan robustsupramolecularheterosynthonassembledbyahydrogenbondandachalcogenbond AT mingyuanxu robustsupramolecularheterosynthonassembledbyahydrogenbondandachalcogenbond AT jiangewang robustsupramolecularheterosynthonassembledbyahydrogenbondandachalcogenbond AT yuzhang robustsupramolecularheterosynthonassembledbyahydrogenbondandachalcogenbond AT weizhouwang robustsupramolecularheterosynthonassembledbyahydrogenbondandachalcogenbond |
| _version_ |
1718412529138401280 |