Open Access
Nature Communications, volume 11, issue 1, publication number 2921
The halogen bond with isocyano carbon reduces isocyanide odor
Publication type: Journal Article
Publication date: 2020-06-10
Journal:
Nature Communications
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 16.6
ISSN: 20411723
PubMed ID:
32523100
General Chemistry
General Biochemistry, Genetics and Molecular Biology
General Physics and Astronomy
Abstract
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 13 C 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. Carbon atoms of various species typically function as acceptors of noncovalent interactions when they are part of a π-system. Here, the authors report their discovery of a noncovalent halogen bond involving the isocyano carbon lone pair, which results in adducts with strongly reduced isocyanide odor.
Citations by journals
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Journal of Structural Chemistry
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Journal of Structural Chemistry
3 publications, 6.67%
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Crystal Growth and Design
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Chemistry - A European Journal
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CrystEngComm
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Journal of Molecular Structure
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2 publications, 4.44%
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Molecules
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Nature Communications
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2 publications, 4.44%
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International Journal of Molecular Sciences
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2 publications, 4.44%
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2 publications, 4.44%
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Chemical Science
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2 publications, 4.44%
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Journal of Organic Chemistry
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Journal of Organic Chemistry
1 publication, 2.22%
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1 publication, 2.22%
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1 publication, 2.22%
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1 publication, 2.22%
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1 publication, 2.22%
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Inorganics
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1 publication, 2.22%
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1 publication, 2.22%
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Russian Chemical Bulletin
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1 publication, 2.22%
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Chemical Physics Letters
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1 publication, 2.22%
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Journal of Computational Chemistry
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1 publication, 2.22%
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Journal of Physical Chemistry Letters
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1 publication, 2.22%
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Chemical Reviews
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1 publication, 2.22%
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ACS Omega
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ACS Omega
1 publication, 2.22%
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Chemical Society Reviews
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Chemical Society Reviews
1 publication, 2.22%
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Dalton Transactions
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Dalton Transactions
1 publication, 2.22%
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Chemical Communications
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Chemical Communications
1 publication, 2.22%
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New Journal of Chemistry
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New Journal of Chemistry
1 publication, 2.22%
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International Journal of Biological Macromolecules
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International Journal of Biological Macromolecules
1 publication, 2.22%
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Journal of the Indian Chemical Society
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Journal of the Indian Chemical Society, 1, 2.22%
Journal of the Indian Chemical Society
1 publication, 2.22%
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Physical Chemistry Chemical Physics
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Physical Chemistry Chemical Physics
1 publication, 2.22%
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Citations by publishers
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12
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Royal Society of Chemistry (RSC)
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Royal Society of Chemistry (RSC)
12 publications, 26.67%
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American Chemical Society (ACS)
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American Chemical Society (ACS)
8 publications, 17.78%
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Wiley
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Wiley
6 publications, 13.33%
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Multidisciplinary Digital Publishing Institute (MDPI)
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Multidisciplinary Digital Publishing Institute (MDPI)
6 publications, 13.33%
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Pleiades Publishing
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Pleiades Publishing
4 publications, 8.89%
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Elsevier
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Elsevier
4 publications, 8.89%
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Springer Nature
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Springer Nature
4 publications, 8.89%
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Scientific Publishers
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Scientific Publishers, 1, 2.22%
Scientific Publishers
1 publication, 2.22%
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- We do not take into account publications that without a DOI.
- Statistics recalculated only for publications connected to researchers, organizations and labs registered on the platform.
- Statistics recalculated weekly.
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Mikherdov A. et al. The halogen bond with isocyano carbon reduces isocyanide odor // Nature Communications. 2020. Vol. 11. No. 1. 2921
GOST all authors (up to 50)
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Mikherdov A., Novikov A. S., Boyarskiy V. P., Kukushkin V. Y. The halogen bond with isocyano carbon reduces isocyanide odor // Nature Communications. 2020. Vol. 11. No. 1. 2921
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TY - JOUR
DO - 10.1038/s41467-020-16748-x
UR - https://doi.org/10.1038%2Fs41467-020-16748-x
TI - The halogen bond with isocyano carbon reduces isocyanide odor
T2 - Nature Communications
AU - Mikherdov, Alexander
AU - Novikov, Alexander S.
AU - Boyarskiy, Vadim P
AU - Kukushkin, Vadim Yu.
PY - 2020
DA - 2020/06/10 00:00:00
PB - Springer Nature
IS - 1
VL - 11
PMID - 32523100
SN - 2041-1723
ER -
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@article{2020_Mikherdov,
author = {Alexander Mikherdov and Alexander S. Novikov and Vadim P Boyarskiy and Vadim Yu. Kukushkin},
title = {The halogen bond with isocyano carbon reduces isocyanide odor},
journal = {Nature Communications},
year = {2020},
volume = {11},
publisher = {Springer Nature},
month = {jun},
url = {https://doi.org/10.1038%2Fs41467-020-16748-x},
number = {1},
doi = {10.1038/s41467-020-16748-x}
}