M. L. S. Cristiano, R. Johnstone, M. Pratt
Dec 15, 1995
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Journal
Acta Crystallographica Section C-crystal Structure Communications
Abstract
Nitration of 3-hydroxyacetophenone gives 2,6-dinitro- 3-hydroxyacetophenone, C8H6N206, in which the nitro groups have entered the sterically least favourable po- sitions in the aromatic nucleus. None of the expected substitution in the 4-position was observed. The two ni- tro groups flanking the carbonyl side chain are different in that one is in the plane of the aryl ring but the other is twisted well out of the plane. Comment During nitration of 3-hydroxyacetophenone to obtain the previously reported 2-nitro-3-hydroxyacetophenone (Butenandt, Hallmann & Beckmann, 1957), a substantial quantity of a new compound was also isolated. 1H NMR spectroscopy showed that there were two ortho H atoms and, by using additivity rules for chemical shifts (Gordon & Ford, 1972), it seemed that the H atoms occupied the 4,5-positions in the aromatic ring indicating that an unexpected substitution had occurred. However, this prediction was not sufficiently clear-cut