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Isonitrile-Derivatized Indole as an Infrared Probe for Hydrogen-Bonding Environments

The isonitrile (NC) group has been shown to be a promising infrared probe for studying the structure and dynamics of biomolecules. However, there have been no systematic studies performed on the NC group as an infrared probe, when it is bonded to an indole ring. Here, we systematically study the NC...

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Detalles Bibliográficos
Autores principales: You, Min, Zhou, Liang, Huang, Xinyue, Wang, Yang, Zhang, Wenkai
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6480494/
https://www.ncbi.nlm.nih.gov/pubmed/30965674
http://dx.doi.org/10.3390/molecules24071379
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author You, Min
Zhou, Liang
Huang, Xinyue
Wang, Yang
Zhang, Wenkai
author_facet You, Min
Zhou, Liang
Huang, Xinyue
Wang, Yang
Zhang, Wenkai
author_sort You, Min
collection PubMed
description The isonitrile (NC) group has been shown to be a promising infrared probe for studying the structure and dynamics of biomolecules. However, there have been no systematic studies performed on the NC group as an infrared probe, when it is bonded to an indole ring. Here, we systematically study the NC stretching mode of two model compounds, 5-isocyano-1H-indole (5ICI) and 5-isocyano-1-methyl-1H-indole (NM5ICI), using Fourier transform infrared (FTIR) spectroscopy. The NC stretching frequency is shown to be strongly dependent on the polarizability of protic solvents and the density of hydrogen-bond donor groups in the solvent when NC is bonded to an indole ring. Infrared pump–probe studies of 5ICI in DMSO and in EtOH further support that the NC stretching mode could be used as a site-specific infrared probe for local environments when NC is bonded to an indole ring.
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spelling pubmed-64804942019-04-30 Isonitrile-Derivatized Indole as an Infrared Probe for Hydrogen-Bonding Environments You, Min Zhou, Liang Huang, Xinyue Wang, Yang Zhang, Wenkai Molecules Article The isonitrile (NC) group has been shown to be a promising infrared probe for studying the structure and dynamics of biomolecules. However, there have been no systematic studies performed on the NC group as an infrared probe, when it is bonded to an indole ring. Here, we systematically study the NC stretching mode of two model compounds, 5-isocyano-1H-indole (5ICI) and 5-isocyano-1-methyl-1H-indole (NM5ICI), using Fourier transform infrared (FTIR) spectroscopy. The NC stretching frequency is shown to be strongly dependent on the polarizability of protic solvents and the density of hydrogen-bond donor groups in the solvent when NC is bonded to an indole ring. Infrared pump–probe studies of 5ICI in DMSO and in EtOH further support that the NC stretching mode could be used as a site-specific infrared probe for local environments when NC is bonded to an indole ring. MDPI 2019-04-08 /pmc/articles/PMC6480494/ /pubmed/30965674 http://dx.doi.org/10.3390/molecules24071379 Text en © 2019 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
You, Min
Zhou, Liang
Huang, Xinyue
Wang, Yang
Zhang, Wenkai
Isonitrile-Derivatized Indole as an Infrared Probe for Hydrogen-Bonding Environments
title Isonitrile-Derivatized Indole as an Infrared Probe for Hydrogen-Bonding Environments
title_full Isonitrile-Derivatized Indole as an Infrared Probe for Hydrogen-Bonding Environments
title_fullStr Isonitrile-Derivatized Indole as an Infrared Probe for Hydrogen-Bonding Environments
title_full_unstemmed Isonitrile-Derivatized Indole as an Infrared Probe for Hydrogen-Bonding Environments
title_short Isonitrile-Derivatized Indole as an Infrared Probe for Hydrogen-Bonding Environments
title_sort isonitrile-derivatized indole as an infrared probe for hydrogen-bonding environments
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6480494/
https://www.ncbi.nlm.nih.gov/pubmed/30965674
http://dx.doi.org/10.3390/molecules24071379
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