Radical-radical interaction through a saturated link: methylenebis-6-oxoverdazyl

David J R Brook; Gordon T Yee

doi:10.1021/jo060165b

Radical-radical interaction through a saturated link: methylenebis-6-oxoverdazyl

J Org Chem. 2006 Jun 23;71(13):4889-95. doi: 10.1021/jo060165b.

Authors

David J R Brook¹, Gordon T Yee

Affiliation

¹ Department of Chemistry, Santa Clara University, Santa Clara, California 95053, USA. djbrook@scu.edu

PMID: 16776518
DOI: 10.1021/jo060165b

Abstract

The diradical methylenebis(1,5-diisopropyl-6-oxoverdazyl) was synthesized by benzoquinone oxidation of the corresponding bis(tetrazane). The diradical crystallizes in the monoclinic space group C2/c with cell parameters a = 21.1411(8) A, b = 12.4781(5) A, c = 8.2457(3) A, beta = 108.638(2) degrees, V = 2061.15 A3, Z = 4. Magnetic measurements indicate the diradical has a singlet ground state and triplet excited state at 150 cm(-1). Interaction between the nonconjugated radical centers is also seen in the UV-vis spectrum as a broad shoulder near 500 nm that is not apparent in the spectrum of the monoradical.