Aromatic solvent effect on the rotational isomerism in 2-hydroxy-5-methyl-3-nitroacetophenone

Konopacka, Aleksandra; Pawełka, Z.

doi:10.1002/poc.988

Cited by 8 publications

(1 citation statement)

References 21 publications

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“…NMR spectroscopy demonstrates the specificity of aromatic solvents, with the compound proton signals being displaced upfield in aromatic solvents compared to the case when these are in magnetically isotropic solvents. As a commonly observed phenomenon, 1 H NMR chemical shifts of polar compounds in aromatic solvents move downfield in comparison to magnetically isotropic solvents [1], usually called the aromatic solvent induced shift (SIS). SIS depends on both the solute site properties and the solvent parameters [2,3].…”

Section: Introductionmentioning

confidence: 99%

Solvent induced 1H NMR chemical shifts of annulenes

Goyary

Sarmah

Goswami

et al. 2023

Preprint

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We investigate the effect of solvent polarity on the 1H NMR chemical shifts of [n]annulenes (n = 12, 18, and 30) using density functional theory and corroborate the computational results with Onsager’s reaction field theory. We observe that there is a complete deshielding of the proton NMR chemical shifts for the outer protons and these shifts depend linearly on the dielectric function of the solvents reaction field for certain annulenes (n = 12 and 30). For the asymmetric C2 structure of [18]annulene, the inner protons are observed to vary nonlinearly with the function of solvent dielectrics due to the influence of the asymmetry parameter “C”, which generates an anisotropic environment inside the annulene ring cavity.

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Section: Introductionmentioning

confidence: 99%