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Updated: Aug 24, 2026

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
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2-nitrophenoxyacetanilide: a chain of rings generated by C-H...O hydrogen bonds
Christopher Glidewell1, John N Low, Janet M S Skakle
1Department of Chemistry, University of Aberdeen, Meston Walk, Old Aberdeen AB24 3UE, Scotland. cg@st-andrews.ac.uk
Abstract:
In molecules of the title compound, C(14)H(12)N(2)O(4), the conformation is dominated by an intramolecular N-H.O hydrogen bond in which one of the nitro O atoms is the acceptor. The molecules are linked by paired C-H.O hydrogen bonds [H.O = 2.41 A, C.O = 3.2990 (17) A and C-H.O = 156 degrees ] into centrosymmetric R(2)(2)(14) dimers; these dimers are linked weakly into chains of alternating R(2)(2)(14) and R(4)(4)(40) rings by a second C-H.O hydrogen bond [H.O = 2.55 A, C.O = 3.5006 (15) A and C-H.O = 162 degrees ].
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