π-Electron delocalisation in the spacer of the O-H…N bridge in Schiff bases. Crystal and molecular structure of 3,5-dimethoxy-2 [(phenylimino) methyl]phenol and 4-methoxy-2-[(phenylimino) methyl] phenol
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Add time:07/25/2019 Source:sciencedirect.com
The spacer built up of NC, two CC, and CO bonds between the H-bond donating OH group and H-bond accepting nitrogen atom in the CN bond in Schiff bases exhibits a significant and strongly diversified degree of the π-electron delocalisation. No dependence between the delocalisation of π electrons and the H-bond strength is observed. The most important factor appears to be the mesomeric effect of the substituents attached to the ring of which a bond is a part of the spacer. This is supported by analysis of the geometry of 3,5-dimethoxy-2[(phenylimino) methyl] phenol and 4-methoxy-2-[(phenylimino) methyl] phenol presented in this study and molecular geometries of 47 well solved X-ray structures retrieved from the CSD.Delocalisation of π-electrons in the spacer of the H-bond depends chiefly on the substituent effect from the ring.
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