1,1'-Dimethoxy-3,3'-dimethyl-3,3'-(hexane-1,6-diyl)bis(triazen-2-ium-2-olate): a nitric oxide donor.
The title compound, C(10)H(24)N(6)O(4), is the most stable type of nitric oxide (NO) donor among the broad category of discrete N-diazeniumdiolates (NO adducts of nucleophilic small molecule amines). Sitting astride a crystallographic inversion center, the molecule contains a symmetric dimethylhexane-1,6-diamine structure bearing two planar O(2)-methylated N-diazeniumdiolate functional groups [N(O)=NOMe]. These two groups are parallel to each other and have the potential to release four molecules of NO. The methylated diazeniumdiolate substituent removes the negative charge from the typical N(O)=NO(-) group, thereby increasing the stability of the diazeniumdiolate structure. The crystal was nonmerohedrally twinned by a 180 degrees rotation about the real [101] axis. This is the first N-based bis-diazeniumdiolate compound with a flexible aliphatic main unit to have its structure analyzed and this work demonstrates the utility of stabilizing the N-diazeniumdiolate functional group by methylation.
Zhou
Zhengrong
Z
Department of Chemistry, University of Michigan, 930 N. University Avenue, Ann Arbor, MI 48109-1055, USA.
Reynolds
Melissa M
MM
Kampf
Jeff W
JW
Meyerhoff
Mark E
ME
D018360:Crystallography, X-Ray; D020030:Nitric Oxide Donors / Q000737:chemistry*; D009829:Oleic Acids / Q000737:chemistry*; D014227:Triazines / Q000737:chemistry*
C534338:1,1'-dimethoxy-3,3'-dimethyl-3,3'-(hexane-1,6-diyl)bis(triazen-2-ium-2-olate); D020030:Nitric Oxide Donors; D009829:Oleic Acids; D014227:Triazines