6533b7d2fe1ef96bd125f452
RESEARCH PRODUCT
false
Klaus BeismannWilhelm NiemannVolker BöhmerWalter VogtDiethard Stotzsubject
chemistry.chemical_compoundchemistryCovalent bondHydrogen bondIntramolecular forceElectrophilePolymer chemistrySubstituentMoleculeReactivity (chemistry)Methylenedescription
The kinetics of the electrophilic bromination of 17 oligonuclear phenolic compounds with molecular bromine in acetic acid were studied at 22°C. Some of these compounds, consisting of up to 6 phenolic units, which are linked in ortho-position by methylene bridges, and having only one (or two) reactive ortho-position(s) at the end of the molecule, were synthesized for the first time. It could be shown, even for hexanuclear compounds, that the variation of substituents at one end of the molecule leads to a change in the reactivity at the other end, that means over a distance of 22 nonconjugated covalent links. So far, this can be explained only by a chain of intramolecular hydrogen bonds between the phenolic hydroxyl groups of adjacent phenolic units. If this chain is interrupted by one methoxy group, a substituent effect cannot be transferred in the same way.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 1983-09-01 | Die Makromolekulare Chemie |