1,2,3-Dithiazolyl and 1,2,35-Dithiadiazolyl Radicals as Spin-Bearing ...

Compound Name: 3-nitro-1,2-naphthaquinone
MW: 203.154 g/mol
Synthesis and Structure:
Appearance:
bright orange powder
Lit. and/or notebook #
and page:
DM 10 -65, p 82
First made on date:
Dec 16, 2011
MacDonald
Made by: Dan J.
Experimental Data: 1,2-napthaquinone (1.2293 g, 7.7727 mmol) was dissolved in 50
mL conc. HNO 3 to give a dark red, opaque reaction mixture which was then heated to
reflux for 30 minutes. After the solution became a clear red/orange, the heat source was
removed and the reaction mixture was allowed to cool to room temperature. The solution
was diluted with 50 mL d.i. H 2 O and extracted with 3 x 100 mL CH 2 Cl 2 . The combined
extracts were dried with Na 2 SO 4 and evaporated to dryness to yield the title compound as
a bright orange powder (0.8139g, 4.006 mmol) 52%, which was used without further
purification.
FTIR (KBr): 3050(w), 1714(m), 1687(s), 1613(m), 1585(m), 1570(m), 1513(s),
1451(m), 1354(s), 1276(s), 1242(s), 1153(w), 1100(w), 1040(w), 979(m), 923(w),
897(w), 881(w), 823(m), 775(s), 764(s), 730(w), 888(w), 656(w), 594(m), 533(m),
506(m), 460(w).
1 HNMR (300 MHz, DMSO-d6): δ 8.67 (s, 1H), δ 8.02 (dd, J = 0.9, 6.6 Hz, 1H), δ 7.91-
7.87 (dt, J = 1.5, 6.0 Hz, 1H), ), δ = 7.80 (dt, J = 0.9, 4.8 Hz, 1H), δ = 7.77 (dt, J = 1.8,
7.2 Hz, 1H).
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