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Communication | Regular issue | Vol 85, No. 4, 2012, pp.821-834
Published online, 6th March, 2012
DOI: 10.3987/COM-12-12439
Synthesis, Structure, and Theoretical Calculations of a Furan-Based Molecular Wire, N-[4-(2-Furanylmethyleneamino)benzylidene]furan-2-amine

Nathan C. Tice,* Jennifer R. Armstrong, Jeremy B. Maddox, Sarah A. Ward, Chad A. Snyder, and Jason O. E. Young

*Department of Chemistry, Butler University, 4600 Sunset Avenue, Indianapolis, IN, 46208, U.S.A.

Abstract

The formation of the furanyl aryl imine N-[4-(2-furanylmethyleneamino)benzylidene]furan-2-amine (1) was accomplished by the condensation of furfural with 1,4-benzenediamine. The structure of the dimine 1 was confirmed by X-ray crystallographic analysis and displayed the expected, “zigzag” or trans conformation about the imine bond. Quantum chemistry calculations were carried out to model the electronic and molecular structure of 1 and to corroborate experimental characterizations.