Details

Autor(en) / Beteiligte

• Abraham, Raymond J.
• Byrne, Jonathan J.
• Griffiths, Lee
• Perez, Manuel

Titel

1H chemical shifts in NMR: Part 23, the effect of dimethyl sulphoxide versus chloroform solvent on 1H chemical shifts

Ist Teil von

• Magnetic resonance in chemistry, 2006-05, Vol.44 (5), p.491-509

Ort / Verlag

Chichester, UK: John Wiley & Sons, Ltd

Erscheinungsjahr

2006

Quelle

MEDLINE

Beschreibungen/Notizen

• The 1H chemical shifts of 124 compounds containing a variety of functional groups have been recorded in CDCl3 and DMSO‐d6 (henceforth DMSO) solvents. The 1H solvent shift Δδ = δ(DMSO) − δ(CDCl3) varies from −0.3 to +4.6 ppm. This solvent shift can be accurately predicted (rms error 0.05 ppm) using the charge model of α, β, γ and long‐range contributions. The labile protons of alcohols, acids, amines and amides give both, the largest solvent shifts and the largest errors. The contributions for the various groups are tabulated and it is shown that for H.C.C.X γ‐effects (X = OH, NH, O, NH.CO) there is a dihedral angle dependence of the γ‐effect. The group contributions are discussed in terms of the possible solvent–solute interactions. For protic hydrogens, hydrogen bonding is the dominant interaction, but for the remaining protons solvent anisotropy and electric field effects appear to be the major factors. Copyright © 2006 John Wiley & Sons, Ltd.