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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...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2019
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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. |
format | Online Article Text |
id | pubmed-6480494 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2019 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
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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