Arulsamy Navamoney, Bohle D Scott, Chuang Chuan-Hung, Moore Raecca C
Department of Chemistry, University of Wyoming, 1000 East University Avenue, Laramie, Wyoming 82071-2000, USA.
J Org Chem. 2008 Oct 17;73(20):8077-80. doi: 10.1021/jo801583f. Epub 2008 Sep 20.
In a stoichiometry-controlled reaction, nitric oxide adds to the enolate of 4-heptanone at ca. -23 degrees C to give mono-, bis-, or tris-diazeniumdiolate (-N2O2(-)) products: potassium 4-heptanone-3,3,5-tris(diazeniumdiolate) (1), potassium butanoate 2,2-bis(diazeniumdiolate) (2), and potassium butanoate 2-diazeniumdiolate (3). The diazeniumdiolate products are stable crystalline solids under ambient conditions and as solids exothermally decompose at high temperatures. Single-crystal X-ray data measured for the dihydrate 3 reveal a new layer aggregation, L4(4)8(8), as octameric water aggregates in a stair conformation which interacts minimally with the cation of the salt.
