Bis-diazeniumdiolates of dialkyldiamines: enhanced nitric oxide loading of parent diamines.
[reaction: see text] The synthesis and characterization of a series of symmetric bis-dialkyldiamine-based diazeniumdiolates, RN[N(O)NO(-)Na(+)](CH(2))(x)()N[N(O)NO(-)Na(+)]R', are reported. Preparation of corresponding intramolecular diazeniumdiolates of the form RN[N(O)NO](-)(CH(2))(x)()NH(2)(+)R' with alkyl groups > (CH(2))(4)CH(3) have been shown previously to lack stability. In contrast, sodium-stabilized bis-diazeniumdiolates of such lipophilic species can be readily formed when these same diamines are reacted with NO in basic media. The resulting compounds release 4 mol of NO per mole of original diamine. This approach enables the synthesis of more lipophilic NO donors than previously possible.
Reynolds
Melissa M
MM
The University of Michigan, Department of Chemistry, Ann Arbor, Michigan 48109-1055, USA.
Zhou
Zhengrong
Z
Oh
Bong K
BK
Meyerhoff
Mark E
ME
D001391:Azo Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D003959:Diamines / Q000138:chemical synthesis* / Q000737:chemistry; D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009569:Nitric Oxide / Q000737:chemistry*; D020030:Nitric Oxide Donors / Q000138:chemical synthesis* / Q000737:chemistry
D001391:Azo Compounds; D003959:Diamines; D020030:Nitric Oxide Donors; C452539:diazeniumdiolate; D009569:Nitric Oxide