H-bond-driven supramolecular architectures of the syn and anti isomers of the dioxime of bicyclo[3.3.1]nonane-3,7-dione

Nicoleta Toşa; Attila Bende; Richard Attila Varga; Anamaria Terec; Ioan Bratu; Ion Grosu

doi:10.1021/jo900484v

H-bond-driven supramolecular architectures of the syn and anti isomers of the dioxime of bicyclo[3.3.1]nonane-3,7-dione

J Org Chem. 2009 May 15;74(10):3944-7. doi: 10.1021/jo900484v.

Authors

Nicoleta Toşa¹, Attila Bende, Richard Attila Varga, Anamaria Terec, Ioan Bratu, Ion Grosu

Affiliation

¹ Faculty of Chemistry and Chemical Engineering, Babes-Bolyai University, 11 Arany Janos, 400028, Cluj Napoca, Romania.

PMID: 19371097
DOI: 10.1021/jo900484v

Abstract

The formation and high stability of the H-bond-driven supramolecular architectures of the syn and anti isomers of the dioxime of bicyclo[3.3.1]nonane-3,7-dione were investigated by single crystal X-ray diffraction, NMR, FTIR, and molecular modeling. Self-assembly of the achiral syn isomer into a cyclic trimer (supramolecular wheel) and of the chiral anti isomer into homochiral cyclic dimers was observed.