N-(p-Toluenesulfonyl)-1-(4′-acetylphenoxy)acrylimidate: Synthesis, Crystal Structure and Theoretical Studies

The formation of N-sulfonyl-1-aryloxy acrylimidate is described, for the first time, from a consecutive process, which involves a CuAAC reaction, a ketenimine formation and subsequent rearrangement between an aryl propargyl ether and a sulfonyl azide. The structure of this newly synthesized compound...

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Published inMolBank Vol. 2022; no. 4; p. M1509
Main Authors Escandón-Mancilla, Flor María, Cedillo-Cruz, Alberto, Gordillo-Cruz, Raúl Eduardo, Martínez-Otero, Diego, Unnamatla, M. V. Basavanag, Cuevas-Yañez, Erick
Format Journal Article
LanguageEnglish
Published Basel MDPI AG 01.12.2022
Subjects
acrylimidate
Aromatic compounds
Azide
Carbonyls
Crystal structure
CuAAC reaction
Hydrogen
ketenimine
Ketones
NMR
Nuclear magnetic resonance
Quantum theory
sulfonyl azide
X ray analysis
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Abstract The formation of N-sulfonyl-1-aryloxy acrylimidate is described, for the first time, from a consecutive process, which involves a CuAAC reaction, a ketenimine formation and subsequent rearrangement between an aryl propargyl ether and a sulfonyl azide. The structure of this newly synthesized compound was analyzed by NMR spectra and unambiguously established by X-ray analysis. In addition, theoretical calculations, which included a Hirshfeld surface, FMO, QTAIM and NCI indices analysis, corroborated the formation of π-π stacking interactions among aromatic rings, as well as C-H···O interactions between vinyl hydrogens with ketone carbonyl oxygen.
AbstractList The formation of N-sulfonyl-1-aryloxy acrylimidate is described, for the first time, from a consecutive process, which involves a CuAAC reaction, a ketenimine formation and subsequent rearrangement between an aryl propargyl ether and a sulfonyl azide. The structure of this newly synthesized compound was analyzed by NMR spectra and unambiguously established by X-ray analysis. In addition, theoretical calculations, which included a Hirshfeld surface, FMO, QTAIM and NCI indices analysis, corroborated the formation of π-π stacking interactions among aromatic rings, as well as C-H···O interactions between vinyl hydrogens with ketone carbonyl oxygen.
Author Cedillo-Cruz, Alberto
Gordillo-Cruz, Raúl Eduardo
Unnamatla, M. V. Basavanag
Escandón-Mancilla, Flor María
Martínez-Otero, Diego
Cuevas-Yañez, Erick
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ContentType Journal Article
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Snippet The formation of N-sulfonyl-1-aryloxy acrylimidate is described, for the first time, from a consecutive process, which involves a CuAAC reaction, a ketenimine...
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SubjectTerms acrylimidate
Aromatic compounds
Azide
Carbonyls
Crystal structure
CuAAC reaction
Hydrogen
ketenimine
Ketones
NMR
Nuclear magnetic resonance
Quantum theory
sulfonyl azide
X ray analysis
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Title N-(p-Toluenesulfonyl)-1-(4′-acetylphenoxy)acrylimidate: Synthesis, Crystal Structure and Theoretical Studies
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