Cargando…

Graphene-catalyzed formation of C≡N bonds via cleavage of C-C and N-O bonds in ethanol and nitrate under room temperature

The cleavage of carbon-carbon bonds and the formation of carbon-nitrogen bonds play crucial roles in chemical synthesis. However, these reactions usually proceed at high temperature and involve multiple steps. Herein, we report an unusual and novel reaction catalyzed by graphene. The C-C bond in eth...

Descripción completa

Detalles Bibliográficos
Autores principales: Xiao, Ding, Wang, Wucong, Gai, Yanzhe, Zhao, Yaping
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group UK 2018
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5789086/
https://www.ncbi.nlm.nih.gov/pubmed/29379108
http://dx.doi.org/10.1038/s41598-018-20238-y
_version_ 1783296200917647360
author Xiao, Ding
Wang, Wucong
Gai, Yanzhe
Zhao, Yaping
author_facet Xiao, Ding
Wang, Wucong
Gai, Yanzhe
Zhao, Yaping
author_sort Xiao, Ding
collection PubMed
description The cleavage of carbon-carbon bonds and the formation of carbon-nitrogen bonds play crucial roles in chemical synthesis. However, these reactions usually proceed at high temperature and involve multiple steps. Herein, we report an unusual and novel reaction catalyzed by graphene. The C-C bond in ethanol and the N-O bond in nitrate can be broken under room temperature, accompanied by the formation of the C≡N bond. We demonstrate these reactions and elucidate their mechanisms by verifying that the product is silver cyanide which was formed when mixing a solution of silver nitrate and ethanol with graphene dispersion in ethanol at room temperature. The pivotal reason for the reaction is the formation of the precipitated silver cyanide. In a broader context, this discovery opens a significant new path for the breakage of the C-C bond in ethanol and the synthesis of nitriles under mild conditions. Also, the graphene was first reported as a catalyst for the room-temperature reaction.
format Online
Article
Text
id pubmed-5789086
institution National Center for Biotechnology Information
language English
publishDate 2018
publisher Nature Publishing Group UK
record_format MEDLINE/PubMed
spelling pubmed-57890862018-02-08 Graphene-catalyzed formation of C≡N bonds via cleavage of C-C and N-O bonds in ethanol and nitrate under room temperature Xiao, Ding Wang, Wucong Gai, Yanzhe Zhao, Yaping Sci Rep Article The cleavage of carbon-carbon bonds and the formation of carbon-nitrogen bonds play crucial roles in chemical synthesis. However, these reactions usually proceed at high temperature and involve multiple steps. Herein, we report an unusual and novel reaction catalyzed by graphene. The C-C bond in ethanol and the N-O bond in nitrate can be broken under room temperature, accompanied by the formation of the C≡N bond. We demonstrate these reactions and elucidate their mechanisms by verifying that the product is silver cyanide which was formed when mixing a solution of silver nitrate and ethanol with graphene dispersion in ethanol at room temperature. The pivotal reason for the reaction is the formation of the precipitated silver cyanide. In a broader context, this discovery opens a significant new path for the breakage of the C-C bond in ethanol and the synthesis of nitriles under mild conditions. Also, the graphene was first reported as a catalyst for the room-temperature reaction. Nature Publishing Group UK 2018-01-29 /pmc/articles/PMC5789086/ /pubmed/29379108 http://dx.doi.org/10.1038/s41598-018-20238-y Text en © The Author(s) 2018 Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/.
spellingShingle Article
Xiao, Ding
Wang, Wucong
Gai, Yanzhe
Zhao, Yaping
Graphene-catalyzed formation of C≡N bonds via cleavage of C-C and N-O bonds in ethanol and nitrate under room temperature
title Graphene-catalyzed formation of C≡N bonds via cleavage of C-C and N-O bonds in ethanol and nitrate under room temperature
title_full Graphene-catalyzed formation of C≡N bonds via cleavage of C-C and N-O bonds in ethanol and nitrate under room temperature
title_fullStr Graphene-catalyzed formation of C≡N bonds via cleavage of C-C and N-O bonds in ethanol and nitrate under room temperature
title_full_unstemmed Graphene-catalyzed formation of C≡N bonds via cleavage of C-C and N-O bonds in ethanol and nitrate under room temperature
title_short Graphene-catalyzed formation of C≡N bonds via cleavage of C-C and N-O bonds in ethanol and nitrate under room temperature
title_sort graphene-catalyzed formation of c≡n bonds via cleavage of c-c and n-o bonds in ethanol and nitrate under room temperature
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5789086/
https://www.ncbi.nlm.nih.gov/pubmed/29379108
http://dx.doi.org/10.1038/s41598-018-20238-y
work_keys_str_mv AT xiaoding graphenecatalyzedformationofcnbondsviacleavageofccandnobondsinethanolandnitrateunderroomtemperature
AT wangwucong graphenecatalyzedformationofcnbondsviacleavageofccandnobondsinethanolandnitrateunderroomtemperature
AT gaiyanzhe graphenecatalyzedformationofcnbondsviacleavageofccandnobondsinethanolandnitrateunderroomtemperature
AT zhaoyaping graphenecatalyzedformationofcnbondsviacleavageofccandnobondsinethanolandnitrateunderroomtemperature