Circular linkage of intramolecular multi-hydrogen bonding frameworks through nucleophilic substitutions of β-dicarbonyls onto cyanuric chloride and subsequent tautomerisation

Nucleophilic substitution reactions of cyanuric chloride with a series of β-dicarbonyls give triply β-dicarbonyl-embedded 1,3,5-triazines. Their subsequent but spontaneous tautomeric transformation leads to circularly linked, intramolecular, multi-hydrogen bonding networks. Their structural elucidat...

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Autores principales: Awatani, Ayano, Suzuki, Masaaki
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2020
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9057380/
https://www.ncbi.nlm.nih.gov/pubmed/35518411
http://dx.doi.org/10.1039/d0ra07677e
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author Awatani, Ayano
Suzuki, Masaaki
author_facet Awatani, Ayano
Suzuki, Masaaki
author_sort Awatani, Ayano
collection PubMed
description Nucleophilic substitution reactions of cyanuric chloride with a series of β-dicarbonyls give triply β-dicarbonyl-embedded 1,3,5-triazines. Their subsequent but spontaneous tautomeric transformation leads to circularly linked, intramolecular, multi-hydrogen bonding networks. Their structural elucidation by X-ray crystallography showed elongated double bonds and shortened single bonds. This is likely due to a resonance hybrid formed via tautomerisation and simultaneous proton transfer.
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spelling pubmed-90573802022-05-04 Circular linkage of intramolecular multi-hydrogen bonding frameworks through nucleophilic substitutions of β-dicarbonyls onto cyanuric chloride and subsequent tautomerisation Awatani, Ayano Suzuki, Masaaki RSC Adv Chemistry Nucleophilic substitution reactions of cyanuric chloride with a series of β-dicarbonyls give triply β-dicarbonyl-embedded 1,3,5-triazines. Their subsequent but spontaneous tautomeric transformation leads to circularly linked, intramolecular, multi-hydrogen bonding networks. Their structural elucidation by X-ray crystallography showed elongated double bonds and shortened single bonds. This is likely due to a resonance hybrid formed via tautomerisation and simultaneous proton transfer. The Royal Society of Chemistry 2020-10-23 /pmc/articles/PMC9057380/ /pubmed/35518411 http://dx.doi.org/10.1039/d0ra07677e Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Awatani, Ayano
Suzuki, Masaaki
Circular linkage of intramolecular multi-hydrogen bonding frameworks through nucleophilic substitutions of β-dicarbonyls onto cyanuric chloride and subsequent tautomerisation
title Circular linkage of intramolecular multi-hydrogen bonding frameworks through nucleophilic substitutions of β-dicarbonyls onto cyanuric chloride and subsequent tautomerisation
title_full Circular linkage of intramolecular multi-hydrogen bonding frameworks through nucleophilic substitutions of β-dicarbonyls onto cyanuric chloride and subsequent tautomerisation
title_fullStr Circular linkage of intramolecular multi-hydrogen bonding frameworks through nucleophilic substitutions of β-dicarbonyls onto cyanuric chloride and subsequent tautomerisation
title_full_unstemmed Circular linkage of intramolecular multi-hydrogen bonding frameworks through nucleophilic substitutions of β-dicarbonyls onto cyanuric chloride and subsequent tautomerisation
title_short Circular linkage of intramolecular multi-hydrogen bonding frameworks through nucleophilic substitutions of β-dicarbonyls onto cyanuric chloride and subsequent tautomerisation
title_sort circular linkage of intramolecular multi-hydrogen bonding frameworks through nucleophilic substitutions of β-dicarbonyls onto cyanuric chloride and subsequent tautomerisation
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9057380/
https://www.ncbi.nlm.nih.gov/pubmed/35518411
http://dx.doi.org/10.1039/d0ra07677e
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AT suzukimasaaki circularlinkageofintramolecularmultihydrogenbondingframeworksthroughnucleophilicsubstitutionsofbdicarbonylsontocyanuricchlorideandsubsequenttautomerisation

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