Dicyclohexyl(sulfanylidene)-λ5-phosphanyl]methanol

William Henderson,Edward Tiekink,Obinna Okpareke,Ainnul Azizan

doi:10.3390/m1069

Abstract

The title compound, [dicyclohexyl(sulfanylidene)-λ5-phosphanyl]methanol, Cy2P(=S)CH2OH (1), was obtained from the reaction between [Cy2P(CH2OH)2]Cl with one molar equivalent of NaOH and an excess of elemental sulfur (powdered). Characterization was by a single-crystal X-ray structure determination as well as IR, and 1D-NMR (1H, 13C{1H}, 31P{1H}), and 2D-NMR (DEPT-135 and HSQC) spectroscopy, ESI mass spectrometry, and elemental analysis. X-ray crystallography on Compound 1 shows the phosphorus atom to be tetrahedrally coordinated within a non-symmetric C3S donor set but with relatively minor distortions from the ideal geometry. In the molecular packing, hydroxyl-O–H⋯S(thione) hydrogen bonds led to supramolecular helical chains along the b-axis direction.

Highlights

Hydroxymethylphosphanes, containing the P-CH2 OH functionality, are an important class of compound on account of their reactivity and coordination chemistry [1]
Hydroxyl-O–H· · · S(thione) hydrogen bonds led to supramolecular helical chains along the b-axis direction
The solid-state structures of compounds containing P-CH2 OH groups have attracted interest for the hydrogen-bonding motifs that can be generated, phosphane chalcogenides, where competition exists between P=S· · · HO and O· · · HO hydrogen bonding

Summary

Introduction

Hydroxymethylphosphanes, containing the P-CH2 OH functionality, are an important class of compound on account of their reactivity (for example, towards amines) and coordination chemistry [1]. Several tertiary hydroxymethylphosphane sulfide derivatives containing one or two CH2 OH groups have been structurally characterized: Fc(CH2 )n P(S)(CH2 OH) where n = 0 [2] or 1 [3], FcCHMeP(S)(CH2 OH)2 [4], CyP(S)(CH2 OH)2 [5], Ph2 P(S)CH2 OH [6], and PhCH2 P(S)(CH2 OH)2 [7]; Fc is ferrocenyl, (η5 -C5 H5 )Fe(η5 -C5 H4 ). In this contribution, the synthesis, spectroscopic characterization, and X-ray crystal structure determination of the title Compound 1 and Figure 1, are described.

Results and Discussion

The structure of Compound

In the molecular packing of

General Information

Crystallography