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Investigation of rotameric conformations of substituted imidazo-[1,2-a]pyrazine: experimental and theoretical approaches
The different rotameric conformations of imidazo-[1,2-a]pyrazine have been synthesized and characterized by means of different experimental techniques, such as NMR, FTIR, and absorption spectroscopy and quantum chemical calculations. The different conformations were stabilized by hydrogen bonds, suc...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
The Royal Society of Chemistry
2018
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9078725/ https://www.ncbi.nlm.nih.gov/pubmed/35540834 http://dx.doi.org/10.1039/c7ra13617j |
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author | Kumar, Gulshan Goel, Richa Paul, Kamaldeep Luxami, Vijay |
author_facet | Kumar, Gulshan Goel, Richa Paul, Kamaldeep Luxami, Vijay |
author_sort | Kumar, Gulshan |
collection | PubMed |
description | The different rotameric conformations of imidazo-[1,2-a]pyrazine have been synthesized and characterized by means of different experimental techniques, such as NMR, FTIR, and absorption spectroscopy and quantum chemical calculations. The different conformations were stabilized by hydrogen bonds, such as OH⋯N, ArH⋯N and ArH⋯ArH. The ground state optimizations and potential energy surface (PES) scanning profiles produced using density functional theory (DFT) show two stable rotameric forms for each molecule. The relative population of the conformations is affected by the strength of the hydrogen bonds. The calculated absorption spectra and isotopic shielding constants were acquired by time-dependent density functional theory (TD-DFT) and gauge invariant atomic orbitals (GIAO)-DFT, respectively. The strength of the hydrogen bonding interactions that resulted in the different conformations was studied by quantum theory of atoms in molecules (QTAIM). |
format | Online Article Text |
id | pubmed-9078725 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2018 |
publisher | The Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
spelling | pubmed-90787252022-05-09 Investigation of rotameric conformations of substituted imidazo-[1,2-a]pyrazine: experimental and theoretical approaches Kumar, Gulshan Goel, Richa Paul, Kamaldeep Luxami, Vijay RSC Adv Chemistry The different rotameric conformations of imidazo-[1,2-a]pyrazine have been synthesized and characterized by means of different experimental techniques, such as NMR, FTIR, and absorption spectroscopy and quantum chemical calculations. The different conformations were stabilized by hydrogen bonds, such as OH⋯N, ArH⋯N and ArH⋯ArH. The ground state optimizations and potential energy surface (PES) scanning profiles produced using density functional theory (DFT) show two stable rotameric forms for each molecule. The relative population of the conformations is affected by the strength of the hydrogen bonds. The calculated absorption spectra and isotopic shielding constants were acquired by time-dependent density functional theory (TD-DFT) and gauge invariant atomic orbitals (GIAO)-DFT, respectively. The strength of the hydrogen bonding interactions that resulted in the different conformations was studied by quantum theory of atoms in molecules (QTAIM). The Royal Society of Chemistry 2018-03-07 /pmc/articles/PMC9078725/ /pubmed/35540834 http://dx.doi.org/10.1039/c7ra13617j Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/ |
spellingShingle | Chemistry Kumar, Gulshan Goel, Richa Paul, Kamaldeep Luxami, Vijay Investigation of rotameric conformations of substituted imidazo-[1,2-a]pyrazine: experimental and theoretical approaches |
title | Investigation of rotameric conformations of substituted imidazo-[1,2-a]pyrazine: experimental and theoretical approaches |
title_full | Investigation of rotameric conformations of substituted imidazo-[1,2-a]pyrazine: experimental and theoretical approaches |
title_fullStr | Investigation of rotameric conformations of substituted imidazo-[1,2-a]pyrazine: experimental and theoretical approaches |
title_full_unstemmed | Investigation of rotameric conformations of substituted imidazo-[1,2-a]pyrazine: experimental and theoretical approaches |
title_short | Investigation of rotameric conformations of substituted imidazo-[1,2-a]pyrazine: experimental and theoretical approaches |
title_sort | investigation of rotameric conformations of substituted imidazo-[1,2-a]pyrazine: experimental and theoretical approaches |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9078725/ https://www.ncbi.nlm.nih.gov/pubmed/35540834 http://dx.doi.org/10.1039/c7ra13617j |
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