Bimanes. 19. Characteristics of the molecular structures of 1,5‐diazabicyclo[3.3.0]octadienediones (9,10‐dioxabimanes) determined by x‐ray crystallography

Israel Goldberg, Joel Bernstein, Edward M. Kosower, Ehud Goldstein, Barak Pazhenchevsky

Research output: Contribution to journalArticlepeer-review

Abstract

The molecular structures of a variety of 1, 5‐diazabicyclo[3.3.0]octadienediones (9, 10‐dioxabimanes), including three 9, 10‐dioxa‐syn‐bimanes, three 4, 6‐bridged 9, 10‐dioxa‐syn‐bimanes, and three 9, 10‐dioxa‐anti‐bimanes, as determined by x‐ray crystallography, are analyzed and compared with respect to planarity, bond distances, bond angles and intermolecular packing. “Planarity” may be the resultant of two non‐planar equilibrium forms, a conclusion based on the anisotropic thermal motion parameters of the central N‐N bond. “Amide”‐type conjugation (N‐C=O) is important in all planar bimanes; peripheral conjugation (N‐C=C‐C = O) is more significant in planar syn‐bimanes and decreased conjugation is evident in the bent bridged syn‐bimanes. Weak CH…O bonds contribute significantly to the crystal packing arrangements.

Original languageEnglish
Pages (from-to)903-912
Number of pages10
JournalJournal of Heterocyclic Chemistry
Volume20
Issue number4
DOIs
StatePublished - 1983

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