4-(Diphenyl­phosphan­yl)benzoic acid

Pei-Hua Zhao; Fu-Yu Sun; Jun-Jie Liu

doi:10.1107/S1600536811034234

. 2011 Aug 27;67(Pt 9):o2454. doi: 10.1107/S1600536811034234

4-(Diphenylphosphanyl)benzoic acid

Pei-Hua Zhao ^a,^*, Fu-Yu Sun ^a, Jun-Jie Liu ^a

PMCID: PMC3200870 PMID: 22059022

Abstract

In the title compound, C₁₉H₁₅O₂P, the dihedral angles between the benzoic acid ring and the phenyl rings are 75.64 (7) and 80.88 (7)°; the dihedral angle between the phenyl rings is 81.35 (7)°. In the crystal, inversion dimers linked by pairs of O—H⋯O hydrogen bonds generate R ₂ ²(8) loops between the head-to-head carboxylic acid groups.

Related literature

For background to phosphine ligands, see: Dydio et al. (2011 ▶). For water-soluble phosphines, see: Katti et al. (1999 ▶); Pinault & Bruce (2003 ▶).

Experimental

Crystal data

C₁₉H₁₅O₂P
M _r = 306.28
Monoclinic,
a = 7.885 (2) Å
b = 28.629 (8) Å
c = 7.066 (2) Å
β = 97.338 (4)°
V = 1581.8 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.18 mm⁻¹
T = 113 K
0.24 × 0.20 × 0.20 mm

Data collection

Rigaku Saturn724 CCD diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T _min = 0.959, T _max = 0.965
15613 measured reflections
3714 independent reflections
3066 reflections with I > 2σ(I)
R _int = 0.049

Refinement

R[F ² > 2σ(F ²)] = 0.040
wR(F ²) = 0.109
S = 1.03
3714 reflections
200 parameters
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811034234/hb6381sup1.cif

e-67-o2454-sup1.cif^{(18.5KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811034234/hb6381Isup4.hkl

e-67-o2454-Isup4.hkl^{(182.1KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811034234/hb6381Isup3.cml

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2ⁱ	0.84	1.79	2.6190 (16)	170

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Symmetry code: (i) Inline graphic .

Acknowledgments

This work was supported financially by the start-up foundation of North University of China.

supplementary crystallographic information

Comment

Phosphine ligands are important intermediates in organic chemistry e.g. (Dydio et al., 2011), Water-soluble phosphines with the hydrophobic group are the most common phosphine lingands used in catalytic and biomedical aspects (Katti et al., 1999; Pinault & Bruce, 2003). The title compound, (I), belongs to the fuctionalized water-soluble phosphines.

The O—H···O hydrogen bonds between the O atom of the carbonyl group and the H atom of the carboxyl group link the molecules into inversion dimers (Table 1).

Experimental

4-iodobenzoic acid (5.0 mmol) and Et3N (10 mmol) were dissolved in CH3CN (30 ml). After the addition of Pb(OAc)2 (0.005 mmol) and Ph2PH (5.0 mmol), the reaction mixture was refluxed for 12 h. All volatiles were removed in vacuo and the obtained residue was dissolved in H2O (15 ml). After addition of KOH (10.0 mmol), the solution was extracted with Et2O. The aqueous solution was acidified with 2 N HCl and again extracted with Et2O. The collected ethereal phases were washed with H2O, dried over MgSO4 and evaporated to get a white precipite. Colourless prisms of (I) were obtained by recrystallization from MeOH at room temperature.