Stacking Interactions: A Supramolecular Approach to Upgrade Weak Halogen Bond Donors; Chemistry - A European Journal; Vol. 28, iss. 70
| Parent link: | Chemistry - A European Journal Vol. 28, iss. 70.— 2022.— [e202201869, 10 p.] |
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| Korporativní autor: | |
| Další autoři: | , , , , , , |
| Shrnutí: | Title screen The co-crystallization of tetracyanobenzene (TCB) with haloarenes ArX provided six new co-crystals TCB ⋅ ArX (ArX=PhCl, PhBr, 4-MeC6H4Cl, 4-MeC6H4Br, 4-MeOC6H4Cl, 1,2-Br2C6H4) which were studied by X-ray diffraction. In these systems, the strong collective effect of π⋅⋅⋅π stacking interactions and lone pair-(X)⋅⋅⋅π-hole-(C) bondings between TCB and ArX promote the strength of X⋅⋅⋅Ncyano halogen bonding (HaB). Theoretical studies showed that the stacking interactions affect the σ-hole depth of the haloarenes, thus significantly boosting their ability to function as HaB donors. According to the molecular electrostatic potential calculations, the σ- hole-(Cl) value (1.5 kcal/mol) in the haloarene 4-MeOC6H4Cl (featuring an electron-rich arene moiety and exhibiting very poor σ-hole-(Cl) ability) increases significantly in the stacked trimer (TCB)2 ⋅ 4-MeOC6H4Cl (12.5 kcal/mol). Theoretical DFT calculations demonstrate the dramatic increase of X⋅⋅⋅Ncyano HaB strength for stacked trimers in comparison with parent unstacked haloarenes. Режим доступа: по договору с организацией-держателем ресурса |
| Jazyk: | angličtina |
| Vydáno: |
2022
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| Témata: | |
| On-line přístup: | https://doi.org/10.1002/chem.202201869 |
| Médium: | Elektronický zdroj Kapitola |
| KOHA link: | https://koha.lib.tpu.ru/cgi-bin/koha/opac-detail.pl?biblionumber=379357 |
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| 200 | 1 | |a Stacking Interactions: A Supramolecular Approach to Upgrade Weak Halogen Bond Donors |f S. V. Baykov, D. M. Ivanov, S. O. Kasatkina [et al.] | |
| 203 | |a Текст |c электронный | ||
| 300 | |a Title screen | ||
| 320 | |a [References: 88 tit.] | ||
| 330 | |a The co-crystallization of tetracyanobenzene (TCB) with haloarenes ArX provided six new co-crystals TCB ⋅ ArX (ArX=PhCl, PhBr, 4-MeC6H4Cl, 4-MeC6H4Br, 4-MeOC6H4Cl, 1,2-Br2C6H4) which were studied by X-ray diffraction. In these systems, the strong collective effect of π⋅⋅⋅π stacking interactions and lone pair-(X)⋅⋅⋅π-hole-(C) bondings between TCB and ArX promote the strength of X⋅⋅⋅Ncyano halogen bonding (HaB). Theoretical studies showed that the stacking interactions affect the σ-hole depth of the haloarenes, thus significantly boosting their ability to function as HaB donors. According to the molecular electrostatic potential calculations, the σ- hole-(Cl) value (1.5 kcal/mol) in the haloarene 4-MeOC6H4Cl (featuring an electron-rich arene moiety and exhibiting very poor σ-hole-(Cl) ability) increases significantly in the stacked trimer (TCB)2 ⋅ 4-MeOC6H4Cl (12.5 kcal/mol). Theoretical DFT calculations demonstrate the dramatic increase of X⋅⋅⋅Ncyano HaB strength for stacked trimers in comparison with parent unstacked haloarenes. | ||
| 333 | |a Режим доступа: по договору с организацией-держателем ресурса | ||
| 461 | |t Chemistry - A European Journal | ||
| 463 | |t Vol. 28, iss. 70 |v [e202201869, 10 p.] |d 2022 | ||
| 610 | 1 | |a труды учёных ТПУ | |
| 610 | 1 | |a электронный ресурс | |
| 610 | 1 | |a crystal engineering | |
| 610 | 1 | |a DFT calculations | |
| 610 | 1 | |a halogen bonding | |
| 610 | 1 | |a noncovalent interactions | |
| 610 | 1 | |a staking | |
| 610 | 1 | |a кристаллотехника | |
| 610 | 1 | |a галогенные связи | |
| 610 | 1 | |a нековалентные взаимодействия | |
| 701 | 1 | |a Baykov |b S. V. |c chemist |c Researcher at Tomsk Polytechnic University, Candidate of Chemical Sciences |f 1987- |g Sergey Valentinovich |3 (RuTPU)RU\TPU\pers\47276 | |
| 701 | 1 | |a Ivanov |b D. M. |c Chemist |c Senior researcher of Tomsk Polytechnic University, Candidate of chemical sciences |f 1992- |g Daniil Mikhaylovich |3 (RuTPU)RU\TPU\pers\47038 | |
| 701 | 1 | |a Kasatkina |b S. O. |g Svetlana Olegovna | |
| 701 | 1 | |a Galmes |b B. |g Bartomeu | |
| 701 | 1 | |a Frontera |b A. |g Antonio | |
| 701 | 1 | |a Resnati |b D. P. |c Chemist |c The Head of the Laboratory of Tomsk Polytechnic University, PhD |f 1955- |g Dzhuzeppe Paolo |3 (RuTPU)RU\TPU\pers\47042 | |
| 701 | 1 | |a Kukushkin |b A. Yu. |g Vadim Yurjevich | |
| 712 | 0 | 2 | |a Национальный исследовательский Томский политехнический университет |b Исследовательская школа химических и биомедицинских технологий (ИШХБМТ) |c (2017- ) |3 (RuTPU)RU\TPU\col\23537 |
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| 856 | 4 | |u https://doi.org/10.1002/chem.202201869 | |
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