3,3'-Dinitro-bis-phenol A

Abstract

THE TITLE COMPOUND [SYSTEMATIC NAME: 2,2'-dinitro-4,4'-(propane-2,2-di-yl)diphenol], C(15)H(14)N(2)O(6), crystallizes with two mol-ecules in the asymmetric unit. Both have a trans conformation for their OH groups, and in each, the two aromatic rings are nearly orthogonal, with dihedral angles of 88.30 (3) and 89.62 (2)°. The nitro groups are nearly in the planes of their attached benzene rings, with C-C-N-O torsion angles in the range 1.21 (17)-4.06 (17)°, and they each accept an intra-molecular O-H⋯O hydrogen bond from their adjacent OH groups. One of the OH groups also forms a weak inter-molecular O-H⋯O hydrogen bond.

Fig. 1.

The molecular structure of (I) with ellipsoids at the 50% level, with H atoms having arbitrary radius.

Fig. 2.

The unit cell, showing hydrogen bonding.

Fig. 3.

Nitration of bisphenol A by nitric acid/acetone mixtures at 0–5°C.

Fig. 4.

1H-NMR spectrum of 3,3'-dinitrobisphenol A.

Fig. 5.

13C-NMR spectrum of 3,3'-dinitrobisphenol A.

Fig. 6.

Ion chromatogram of the silylated product of 3,3'- dinitrobisphenol A.

Fig. 7.

Electron ionization fragmentation of the silylated product of 3,3'-dintrobisphenol A.

Fig. 8.

Proposed routes of fragmentation of the molecular ion of silylated 3,3'-dinitrobisphenol A.