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.
The University of Michigan, Department of Chemistry, Ann Arbor, Michigan 48109-1055, USA.
Melissa M
MM
Reynolds
Zhengrong
Z
Zhou
Bong K
BK
Oh
Mark E
ME
Meyerhoff
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