Synthesis and dynamic NMR studies of novel hydantoin and thiohydantoin derivatives. Crystal structure of diethyl 2-(4,4-diaryl-2,5-dioxoimidazolidin-1-yl) fumarate and diethyl 2-(4,4-diaryl-2-mercapto-5-oxo-4,5-dihydro-1H-imidazol-1-yl)fumarate

Mohammad M. Ghanbari, Marzieh Jamali, Gyula Batta, Attila C. Bényei

Research output: Article

Abstract

The reaction of stoichiometric amounts of dialkyl acetylenedicarboxylates with triphenylphosphine in the presence of hydantoins or thiohydantoins afforded stable crystalline phosphorus ylides. These compounds undergo smooth elimination of PPh3 to produce dialkyl 2-(4,4-diaryl-2,5-dioxoimidazolidin-1-yl)fumarate, 4 or dialkyl 2-(4,4-diaryl-2-mercapto-5-oxo-4,5-dihydro-1H-imidazol-1-yl)fumarate, 7. Single crystal X-ray diffraction study on 4b and 7b proved the structures unambiguously with C=O and SH functionality at the 2-position of the imidazole ring, respectively. Dynamic effects were observed in the NMR spectra of these compounds and were attributed to restricted rotation around the carbon-nitrogen single bonds. Rotational energy barrier (ΔG#) for their interconversion process of rotational isomers equals to (53.6 and 17.2) ± 2 kcal mol-1.

Original languageEnglish
Pages (from-to)309-313
Number of pages5
JournalJournal of Chemical Research
Volume41
Issue number5
DOIs
Publication statusPublished - máj. 2017

ASJC Scopus subject areas

  • Chemistry(all)

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