Structure of 4'-amino-2,2,3'-trichloracetophenone, C8H6Cl3NO

De, Amitabha

doi:10.1107/s0108270184010271

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1985

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“…This lengthening may be attributed to the delocalization of the n-electron cloud of the keto bond as is evidenced by a negative charge on O(1) and a positive charge on the C(7) atom calculated by the CNDO/2 method (Pople & Beveridge, 1970). The C(1)-C(7) bond is considerably shorter than the similar bond in p-hydroxyacetophenone (1.49A) (Vainshtein, Lobanova & Gurskaya, 1974) and 4'-chloro-5'-(dichloroacetyl)-2'-methylacetanilide [1.495 (3)A] (Banerjee, 1983) and is slightly shorter than those in p-aminoacetophenone [1.468 (5) A] (Haisa et al, 1976) and 4'-amino-2,2,3'-trichloroacetophenone [ 1.467 (9) A] (De, 1984). This, together with the narrowing of the endocyclic bond angle at C(1) from the sp 2 value, indicates conjugation between the phenyl ring and the dichloroacetyl group (Domenicano, Vaciago & Coulson, 1975).…”

Section: Introductionmentioning

confidence: 99%