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Kin~Tics and Mechanism of Oxidation of Phosphinic, Phenylphosphinic and Phosphorous Acids by Pyridinium Bromochromate

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Kin~Tics and Mechanism of Oxidation of Phosphinic, Phenylphosphinic and Phosphorous Acids by Pyridinium Bromochromate Vol.Indian 33AI J<ltmal July 1994,of Chemistry pp. 622-626 Kin~tics and mechanism of oxidation of phosphinic, phenylphosphinic and phosphorous acids by pyridinium bromochromate Anjali Grover, Seema Varshney & Kalyan K Banerji* Department of Chemistry, J.N.Y. University, Jodhpur 342 005 Received 10 January 1994; revised and accepted 11 March 1994 The title reaction is of second order, first order with respect to each reactant. The reaction is alysed by H + ions and the H + dependence has the form kobs = a + b [H+]. The oxidation of phos• p . 'c and phosphorous acids exhibits a substantial primary kinetic isotope effect. The reaction has b en studied in nineteen organic solvents and the effect of solvent is analysed using Taft's and S ain's multiparametric equations. The participation of the tautomeric forms of the phosphorus o yacids, in the oxidation process, has been discussed. It has been concluded that the trichlorinated fo m of the phosphorus oxyacid does not participate in the oxidation process and a suitable mechan• is has been proposed. Pyrid' urn bromochromate (PBC) has been re• Stoichiometry ported as a mild and selective oxidizing reagent in The oxidation of lower oxyacids of phospho• synthe c organic chemistry!. There seems to be rus leads to the formation of corresponding oxy• « only 0 e report on the mechanistic aspects of ox• acids containing phosphorus in a higher oxida• idation by PBC2. We have been interested in the tion state. kinetic of reactions of complexed Cr(VI) species Reaction mixtures were prepared containing a and ha e reported the kinetics and mechanism of known excess of phosphinic or phosphorous acid. oxidati n of lower oxyacids of phosph6rus by On the completion of reaction, amount of phos• pyrid' urn fluorochromate (PFC) and pyridinium phorous acid formed in the oxidation of phos• chloro hromate (PCC)3,4. It was observed that the phinic acid and the residual reductant in the oxi• oxidati ns by PFC and PCC presented different dation of phosphorous acid were determined by kinetic pictures. Further, the lower oxyacids of the literature method. To determine the stoichi• phosp rou are reported to exist in two tautom• ometry of the oxidation of PPA, a known excess eric fo rns5 and it is of interest to determine the of PBC was treated with PPA and the residual nature f tautomer of the oxyacids involved in the PBC was determined spectrophotometrically at oxidati n process. We report in this paper, the 356 nm after the completion of the reaction. The kinetic of the oxidation of phosphinic (PA), oxidation state of chromium in a completely re• phenyl hosphinic (PPA), and phosphorous (POA) duced :t;eaction mixture, determined by iodometric acids y PBC in DMSO as solvent. Mechanistic titrations, was 4.07 ± 0.18. aspects are discussed. Kinetic measurements Materi s and Methods The reactions were carried out under pseudo• The oxyacids were commercial products (Flu• first order conditions by maintaining a large ex• ka) an were used as supplied. PBC was prepared cess of [oxyacid] over [PBC]. The solvent was by the reported method!. Deuteriated phosphinic DMSO, unless otherwise specified. The reactions and p osphorous acids were prepared by repea• were followed, at constant temperatures ( ± 0.1 K), tedly issolving the oxyacid in deuterium oxide by monitoring the decrease in [PBe] spectropho• (BAR , 99.4%) and evaporating water and the to metrically at 356 nm. No other reactant or pro• excess f deuterium oxide6• The isotopic purity of duct has any significant absorption at this wave• the de teriated PA and POA, as determined by length. The pseudo-first order rate constant, kobs, NMR pectra, was 91 ± 4% and 93 ± 5% respect• was evaluated from the linear (r= 0.990-0.999) ively. he solvents were purified by the usual plots of log [PBC] against time. Duplicate kinetic metho S7. runs showed that the rate constants were reprod- 11 II I 11111 I '" i", I _I;~! IN !11' II '"I' ". ' i l"'~iI't'" "",""" ,," II I' Ii'i BANERJI et at.: KINETICS OF PHOSPHINIC, PHENYLPHOSPHINIC & PHOSPHOROUS ACIDS 623 ucible to within ± 3%. Simple and multivariate dependence has the form kobs = a + b [H +]. Addi• linear regression analyses were carried out by the tion of a radical scavenger, acrylonitrile, had no least-squares method on a personal computer. effect on the rate (Table 1). Results Kinetic isotope effect The analysis of product formed in the oxidation To ascertain the importance of the cleavage of a of PA showed that 1.01 ± 0.05 mole of the pro• P - H bond in the rate-determining step, oxidation duct is formed for every mole of PBC consumed. of deuteriated PA and POA was studied. Results Similarly in the oxidation of POA, amount of the showed the presence of a substantial primary kin• oxyacid consumed per mole of PBC consumed is etic isotope effect (at 303 K, kH/ ko was found to 1.01 ± 0.03. In the oxidation of PPA, the amount be 5.56 for PA and 5.08 for POA). of PBC consumed per mole of the oxyacid o~d• ized is 1.03 ± 0.03. The overall reaction may be Effect of temperature and solvents written as in Eq. (1). The reaction rates at different temperatures were determined and the activation parameters RPH(O)OH + Cr02BrO-PyH+ --+ were calculated (Table 2). The oxidation of PPA RP(O)(OHh + CrOBrO-PyH+ ... (1) was studied in 19 different organic solvents. The choice of solvents was limited by the solubility of PBC undergoes a 2-electron change. This is in PBC and its reaction with primary and secondary accord with the earlier observations with both alcohols. There was no reaction with the solvents PFC and PCC34. Chromium(IV) species are chosen. Kinetics were similar in all the solvents. known to be less stable. However, the reduction The values of k2 are recorded in Table 3. products of both PCC8 and PFC9 have been well characterised to be Cr(IV) species. Discussion The oxidation of PA resulted in the formation Rate laws of POA. PA is oxidized at ca. five times the rate The reaction is first order with respect to PBC. of oxidation of POA. To reduce the effect of fur• Further, the pseudo-first order rate constnat, kobs' ther oxidation of POA on the kinetics and stoichi• is independent of initial [PBC]. The reaction is of ometry of the oxidation of PA, the concentration first order with respect to the oxyacid also. The of oxyacid was always kept in large excess over reaction is catalysed by hydrogen ions. The H + the concentration of PBC. 0.1 Table I-Rate8.900.120.03.2015.00.120.1330.27.1211.90.1005.1017.90.16818.00.1426.45133.00.960.480.0*0.120.30.240.1218.80.80.480.00.720.40419.453.80.00.120.120.51.200.54025.672.00.6360.4070.27835.60.3980.4812.935.90.00.0670.4020.480.23524.233.089.30.00.41212.135.00.0PPAPOA12.513.012.635.336.0(mol(moldm-3)dm-3)0.325[oxyacid]0.09.06[W] constants104 forkobs oxidation(s - I) of the oxyacids by PBC at 303 K in DMSO (mol dm-3) PA 1.04.02.08.01.0 1Q3[PBC] *contained 0.001 mol dm -3 acrylonitrile 624 INDIAN J CHEM, SEe. A, JULY 1994 by PBC in DMSO Table 2-A~id Temperature dependence]()3k2(dm'mol-1s-l) and the activation parameters of thefj.H* oxidation of oxyacidsfj.S* of phosphorus fj.G* (kJmol-l) (j mol-I K-I) (kJ mol-I) 32312.52.254.9521.43034.609.003137.4216.745.7±0.7-1400.561.2529351.836.339.2± K ± 0.6 1.3-131-153±2 ±±2 3 PA 2.67 86.9±0.6 PIA 84.5 ±0.5 90.6 ± 1.0 Table 3- Effect of solvents on the oxidation of phenylphosphinic acid by PBC at 303 K Solvent lO4 k2 Solvent 104, k2 (dm' mol-I S-I) (dm) mo!-I S-I) Chloroform 1,Carbon 2-DimethoxyethaneTetrahydrofurant-ButylAcetophenoneAceticEthylDioxane7.76 disulphideacetate alcohol12518.6 acid12.64.500.6333.114.5Toluene3.164.4728.24.000.127.9420.91.3522.442.72.40 Dimethylformamide1,2-DichloroethaneDichloromethaneNitrobenzeneCyclohexaneButanoneBenzeneAcetoneDMSO served H+ dependence suggests that the R z = 0.9343; sd = 0.19; n = 17; tp = 0.20 reaction ollows two mechanistic pathways, one log kz = - 4.76 + 2.50 (± 0.22).1l'* acid-inde endent and another acid-dependent. + 0.26 (± 0.18),8 ... (5) The aci catalysis may well be attributed to a protonati n of PBC (Eq. 2) to yield a protonated R z = 0.9098; sd = 0.22; n = 17; tp = 0.23 Cr(VI) s ecies which is a stronger oxidant and log kz = - 4.71 + 2.57 (± 0.23).1l'* .. '. (6) electrop Ie. Formation of a protonated Cr(VI) species s earlier been postulated in the reac• rZ = 0.8972; sd = 0.22; n = 17; tp = 0.24 tions of s cturally similar PCCl . log kz = - 3.96 + 0.73 (± 0.55),8 ... (7) + PyHOCr zBr + H+ ~ PyHOCr(OH)OBr ... (2) rZ = 0.1064; sd = 0.65; n = 17; tp = 0.85 So/vent Here n is the number of data points and tp is Exner's statistical parametertz. The r e constants of oxidation, kz, in seven• teen solv nts (CSz and acetic acid were not con• Kamlet and Taft's triparametric equation ex• sidered the complete range of solvent parame• plain> 93% of the effect of solvent on the oxida• ters wer not available) were correlated in terms tion.
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