title: The halogen bond with isocyano carbon reduces isocyanide odor
metadata.name: dc.contributor.author
metadata.value: Mikherdov, Alexander S
metadata.lang: -
metadata.name: dc.contributor.author
metadata.value: Novikov, Alexander S
metadata.lang: -
metadata.name: dc.contributor.author
metadata.value: Boyarskiy, Vadim P
metadata.lang: -
metadata.name: dc.contributor.author
metadata.value: Kukushkin, Vadim Yu
metadata.lang: -
metadata.name: dc.date.accessioned
metadata.value: 2020-06-15T16:53:20Z
metadata.lang: -
metadata.name: dc.date.available
metadata.value: 2020-06-15T16:53:20Z
metadata.lang: -
metadata.name: dc.date.issued
metadata.value: 2020-06-10
metadata.lang: -
metadata.name: dc.identifier
metadata.value: 10.1038/s41467-020-16748-x
metadata.lang: -
metadata.name: dc.identifier.issn
metadata.value: 10.1038/s41467-020-16748-x
metadata.lang: -
metadata.name: dc.identifier.uri
metadata.value: http://hdl.handle.net/11701/18305
metadata.lang: -
metadata.name: dc.description.abstract
metadata.value: Predominantly, carbon atoms of various species function as acceptors of noncovalent interactions when they are part of a π-system. Here, we report on the discovery of a halogen bond involving the isocyano carbon lone pair. The co-crystallization or mechanochemical liquid-assisted grinding of model mesityl isocyanide with four iodoperfluorobenezenes leads to a series of halogen-bonded adducts with isocyanides. The obtained adducts were characterized by single-crystal and powder X-ray diffraction, solid-state IR and 13C NMR spectroscopies, and also by thermogravimetric analysis. The formation of the halogen bond with the isocyano group leads to a strong reduction of the isocyanide odor (3- to 46-fold gas phase concentration decrease). This manipulation makes isocyanides more suitable for laboratory storage and usage while preserving their reactivity, which is found to be similar between the adducts and the parent isocyanide in some common transformations, such as ligation to metal centers and the multi-component Ugi reaction.
metadata.lang: en_GB
metadata.name: dc.language.iso
metadata.value: en
metadata.lang: en_GB
metadata.name: dc.title
metadata.value: The halogen bond with isocyano carbon reduces isocyanide odor
metadata.lang: en_GB
metadata.name: dc.type
metadata.value: Article
metadata.lang: en_GB
resources.filename: Mikherdov_et_al-2020-Nature_Communications.pdf
resources.url: https://dspace.spbu.ru/bitstream/11701/18305/1/Mikherdov_et_al-2020-Nature_Communications.pdf
resources.format: Adobe PDF
resources.size: 1,49 MB