Chemical shift and coupling constant analysis of dibenzyloxy disulfides

Eric G. Stoutenburg, Ganna Gryn'Ova, Michelle L. Coote, Ronny Priefer

Research output: Contribution to journalArticlepeer-review

Abstract

Dialkoxy disulfides have found applications in the realm of organic synthesis as an S2 or alkoxy donor, under thermal and photolytic decompositions conditions, respectively. Spectrally, dibenzyloxy disulfides possess an ABq in the 1H NMR, which can shift by over 1.1 ppm depending on the substituents present on the aromatic ring, as well as the solvent employed. The effect of the said substituents and solvent were analyzed and compared to the center of the ABq, geminal coupling, and the differences in chemical shifts of the individual doublets. Additionally, quantum-chemical calculations demonstrated the intramolecular H-bonding arrangement, found within the dibenzyloxy disulfides.

Original languageEnglish
Pages (from-to)1924-1931
Number of pages8
JournalSpectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy
Volume136
Issue numberPart C
DOIs
Publication statusPublished - 5 Feb 2015
Externally publishedYes

Keywords

  • AB quartet
  • Computational
  • F-value
  • Keywords Dibenzyloxy disulfides
  • Swain and Lupton's

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