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1H, 13C and 17O NMR study of chlorovanillins and some related compounds

✍ Scribed by Erkki Kolehmainen; Katri Laihia; Juha Knuutinen; Juha Hyötyläinen

Publisher
John Wiley and Sons
Year
1992
Tongue
English
Weight
474 KB
Volume
30
Category
Article
ISSN
0749-1581

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✦ Synopsis

Abstract

^1^H, ^13^C and ^17^O NMR chemical shifts and ^n^J(H,H), ^1^J(C,H) and ^3^J(C‐6, H‐formyl) spin—spin coupling constants of chlorinated vanillins (3‐methoxy‐4‐hydroxybenzaldehydes) were determined. The variation in the long‐range ^4^J(H,H) value between the formyl proton and an ortho‐proton suggests that the ortho‐substituent strongly forces the formyl group out of the aromatic plane. This can also be observed by considering the ^3^J(C‐6,H‐formyl) values and the ^13^C and ^17^O NMR chemical shifts. The ^17^O NMR chemical shifts show a linear correlation with the torsion angle of the formyl group calculated by molecular mechanics. The ^13^C and ^17^O NMR chemical shifts of the methoxyl group also possess strong predictive power in estimating the torsional characteristics of this group.

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