4-(4-Nitro­phenoxy)biphen­yl

Zareen Akhter; Toheed Akhter; Michael Bolte; M Amin Baig; Humaira M Siddiqi

doi:10.1107/S1600536809007417

. 2009 Mar 6;65(Pt 4):o710. doi: 10.1107/S1600536809007417

4-(4-Nitrophenoxy)biphenyl

Zareen Akhter ^a,^*, Toheed Akhter ^a, Michael Bolte ^b, M Amin Baig ^a, Humaira M Siddiqi ^a

PMCID: PMC2968949 PMID: 21582447

Abstract

The two phenyl rings of the biphenyl unit of the title compound, C₁₈H₁₃NO₃, are almost coplanar [dihedral angle 6.70 (9)°]. The nitrophenyl ring, on the other hand, is significantly twisted out of the plane of the these two rings, making dihedral angles of 68.83 (4)° with the middle ring and 62.86 (4)° with the end ring. The nitro group is twisted by 12.1 (2)° out of the plane of the phenyl ring to which it is attached.

Related literature

The title compound is a precursor of amine which is a useful curing agent of epoxy resins. For the properties and applications of epoxy resins, see: Boey & Yap (2001 ▶); Bonnaud et al. (2004 ▶); de Moris et al. (2007 ▶); Van de Grampel et al. (2005 ▶); Agag & Takeichi (1999 ▶); Kagathera & Parsania (2001 ▶); Kagathera & Parsania (2001 ▶).

Experimental

Crystal data

C₁₈H₁₃NO₃
M _r = 291.29
Monoclinic,
a = 9.6435 (7) Å
b = 5.8648 (3) Å
c = 24.6884 (18) Å
β = 95.704 (6)°
V = 1389.39 (16) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 173 K
0.44 × 0.37 × 0.13 mm

Data collection

STOE IPDS II two-circle-diffractometer
Absorption correction: none
16020 measured reflections
2556 independent reflections
2187 reflections with I > 2σ(I)
R _int = 0.052

Refinement

R[F ² > 2σ(F ²)] = 0.040
wR(F ²) = 0.118
S = 1.07
2556 reflections
200 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Data collection: X-AREA (Stoe & Cie, 2001 ▶); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablocks I, Za12. DOI: 10.1107/S1600536809007417/ww2140sup1.cif

e-65-0o710-sup1.cif^{(18.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809007417/ww2140Isup2.hkl

e-65-0o710-Isup2.hkl^{(125.6KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The authors are grateful to the Department of Chemistry, Quaid-I-Azam University, Islamabad, Pakistan, and the Institute for Inorganic Chemistry, University of Frankfurt, Germany, for providing laboratory and analytical facilities.

supplementary crystallographic information

Comment

Epoxy resins are a versatile group of crosslinked polymers that has excellent chemical resistance, good electrical insulating properties, good adhesion to glass and metal and can be easily fabricated (Boey & Yap, 2001). Variety of properties helps epoxy resins to meet performance requirements of some demanding applications (Bonnaud et al., 2004). These include areas as diverse as construction, electronics, adhesives and coatings (de Moris et al., 2007). The usefulness of epoxy resins is often limited due to their inherent brittleness arising from crosslinking structure (van de Grampel et al., 2005). Development of approaches for toughening epoxy resins without sacrificing modulus and glass transition temperature (Tg) would lead to an increase in their applications (Kagathera & Parsania, 2001). One such approach is the curing of epoxy resins with different curing agents (Agag & Takeichi, 1999). The title compound is a precursor of amine which is a useful curing agent of epoxy resins.

The two phenyl rings of the biphenyl moiety of the title compound are almost coplanar [dihedral angle 6.70 (9)°]. The nitrophenyl ring, on the other hand, is significantly twisted out of the plane of the these two rings [68.83 (4)° and 62.86 (4)°]. The nitro group is twisted by 12.1 (2)° out of the plane of the phenyl ring to which it is attached.

Experimental

A 500 ml two neck round bottom flask was equipped with condenser and thermometer and was charged with (0.059 moles) biphenyl-4-ol, (0.059 moles) anhydrous potassium carbonate and (0.059 moles) 4-chloronitrobenzene in 180 ml of DMF. Reaction mixture was heated for 24 h at 120°C. The reaction was carried out in the inert atmosphere of nitrogen. Progress of reaction was measured by TLC [1:1, ethyl acetae, n-hexane]. After completion, the reaction mixture was poured into 600 ml of water to give yellow precipitates. These precipitates were collected by filtration and washed with water several times. Recrystallization of the residue in n-hexane afforded the title compound (86%) (m.p 142–144°C)