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

Compound Name: 6,6′-dinitro-1,1′-binaphthyl-3,3′,4,4′-tetraone
MW: 404.29 g/mol
Synthesis and Structure:
Appearance:
Lit. and/or notebook #
and page:
DM 10 -35, p 40
First made on date:
Nov 2, 2011
Made by:
Dan J. MacDonald
Experimental Data: 1,2-napthaquinone (2.1562 g, 13.633 mmol) was dissolved in conc.
H 2 SO 4 (20 mL) to give a deep blue solution. Approximately 2 mL of conc. HNO 3 was
added to give a dark red reaction mixture which was subsequently heated gently in a
warm water bath at 65 °C for 45 min. The solution was cooled and then poured on 100 g
of crushed ice to give a thick orange precipitate which was filtered and washed with a
minimum of water followed by 20 mL of ether, dried in the air and used without further
purification (2.6236 g, 12.9788 mmol) 95% yield. Crystals suitable for X-ray diffraction
were grown from slow evaporation of dioxane.
FTIR (KBr): 3104(w), 3072(w), 3042(w), 1713(m), 1671(s), 1592(m), 1571(w),
1522(s), 1419(w), 1349(s), 1330(m), 1276(s), 1245(m), 1217(w), 1198(w), 1085(w),
1059(w), 1008(w), 917(w), 862(w), 844(w), 799(w), 785(w), 723(m), 506(w), 432(w)
1 HNMR (300 MHz, DMSO-d6): δ 8.64 (d, J = 2.4 Hz, 2H), δ 8.36 (dd, J = 8.4, 2.4 Hz,
2H), δ 7.80 (d, J = 8.7 Hz, 2H), δ =, 6.631 (s, 2H).
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