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

Compound Name: 3,4-dioxo-3,4-dihydronaphthalen-2-aminium chloride
MW: 209.632 g/mol
Synthesis and Structure:
Appearance:
dark red powder
Lit. and/or notebook #
and page:
DM 11-2, p 2
First made on date:
Jan 10, 2012
MacDonald
Made by: Dan J.
Experimental Data: Pd/C (10 mg) was added to a solution of 3-nitronaphthalene-1,2-
dione (0.7890g, 3.884 mmol) in bubble de-gassed MeOH (80 mL). A balloon was fitted
to the middle neck of a three neck flask and the system was flushed with H 2 three times.
The balloon was then inflated once more with H 2 and the system was sealed. The reaction
mixture was stirred for 1h at room temperature. The red solution was then filtered to
remove the Pd/C and 5 mL of conc. HCl was added and stirred overnight. The MeOH
was then rotaryevaporated to afford the title compound as a dark red powder (0.5173 g,
3.012 mmol) 77.55% yield. Used without further purification.
FTIR (KBr): 3057(s, broad), 2582(w), 1736(m), 1642(s), 1611(m), 1592(s), 1558(s),
1509(s), 1473(s), 1396(s), 1361(w), 1339(w), 1260(m), 1228(m), 1195(m), 1104(w),
1071(s), 1023(s), 964(m), 918(m), 871(m), 839(m), 766(s), 737(s), 713(m), 680(w),
648(w), 605(w), 548(m), 443(m)
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