Phosphine Adducts Research Articles

C−H Activation Reactions on Rh(I)−Ethylene Complexes of the Hydrotris(3,5-dimethylpyrazolyl)borate Ligand, TpMe2

N-donor Lewis bases such as acetonitrile or pyridine react with the Rh(I) compound TpMe2Rh(C2H4)2 (1) to give the Rh(III) derivatives TpMe2Rh(CHCH2)(C2H5)(L) (2, 3) as the kinetic products of the reactions. Upon heating at 60 °C, the acetonitrile adduct 2 converts into TpMe2Rh(C2H4)(NCMe) (5). Under similar conditions, 2 is able to induce the activation of one of the C−H bonds of C6H6, in a process that involves the intermediacy of 1, as demonstrated by isotopic labeling studies. The phosphine adducts TpMe2Rh(C2H4)(PR3) (R = Me, Et) are also efficient reagents for the C−H bond activation of C6H6, py, or thiophene. In the latter case, rupture of the C−S bond is also detected, although the C−S bond activation complexes are thermodynamically disfavored with respect to those derived from the cleavage of one of the α-C−H bonds.

ChemInform Abstract: Synthesis of Diastereomerically Pure Monoisopinocampheylcyanoborane Adducts of Phosphines. Direct Evidence of an SN2 Substitution at a Boron Atom.

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Lewis Acid Properties of Tris(pentafluorophenyl)borane. Structure and Bonding in L−B(C6F5)3 Complexes

A variety of donor adducts of tris(pentafluorophenyl)borane were experimentally generated by reaction of a Lewis base with an excess of B(C6F5)3 in pentane. In this way, nitrile complexes (C6F5)3B·NCR (R = CH3 1a, p-CH3−C6H4 1b, p-NO2−C6H4 1c), isonitrile complexes (C6F5)3B·CNR (R = C(CH3)3 3a, C(CH3)2CH2C(CH3)3 3b, 2,6-(CH3)2−C6H3 3c), and the phosphine adduct (C6F5)3B·P(C6H5)3 (6) could be prepared. The compounds were characterized by IR and NMR spectroscopy and by X-ray structure analyses (1a, 1c, 3a, 3b, and 6). Coordination of the nitriles as well as the isonitriles to the neutral Lewis acid leads to a substantial increase in the C⋮N bond strength. This is evident from a marked shift of the ν̃C⋮N IR band to higher wavenumbers, and this interpretation is supported by the small but experimentally significant decrease of the C⋮N bond length observed by X-ray diffraction. The experimental work is complemented by a density functional study on the model complexes (C6F5)3B·L, L = CNCH3, NCCH3, PH3, CO. A detailed analysis revealed that the bonding in (C6F5)3B·L complexes is mainly dominated by electrostatic interaction, which in turn is responsible for the observed structural and spectroscopic changes. In the context of this work, the bonding of the neutral B(C6F5)3 Lewis acid is compared to the positively charged organometallic d0-Cp3M+ system (M = Zr, Hf). It was found that electrostatic effects are more pronounced for B(C6F5)3 than for the transition metal fragments. The question as to the existence of a nonclassical main group carbonyl complex, (C6F5)3B·CO, is addressed.

Synthesis of Diastereomerically Pure Monoisopinocampheylcyanoborane Adducts of Phosphines. Direct Evidence of an SN2 Substitution at a Boron Atom

ADVERTISEMENT RETURN TO ISSUEPREVCommunicationNEXTSynthesis of Diastereomerically Pure Monoisopinocampheylcyanoborane Adducts of Phosphines. Direct Evidence of an SN2 Substitution at a Boron AtomPatrick Vedrenne, Valérie Le Guen, Loïc Toupet, Thierry Le Gall, and Charles MioskowskiView Author Information Département de Biologie Cellulaire et Moléculaire CEA-Saclay, Service des Molécules Marquées, Bât. 547 F-91191 Gif-sur-Yvette Cedex, France Groupe Matière Condensée et Matériaux, UMR CNRS 6626 Bât. 11 A, Université de Rennes 1, Campus de Beaulieu F-35042 Rennes Cedex, France Laboratoire de Synthèse Bio-Organique associé au CNRS Faculté de Pharmacie, Université Louis Pasteur 74 route du Rhin, BP 24, F-67401 Illkirch, France Cite this: J. Am. Chem. Soc. 1999, 121, 5, 1090–1091Publication Date (Web):January 22, 1999Publication History Received9 October 1998Published online22 January 1999Published inissue 1 February 1999https://doi.org/10.1021/ja983566kCopyright © 1999 American Chemical SocietyRIGHTS & PERMISSIONSArticle Views566Altmetric-Citations32LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InReddit Read OnlinePDF (104 KB) Get e-AlertsSupporting Info (1)»Supporting Information Supporting Information SUBJECTS:Adducts,Boron,Group 15 compounds,High-performance liquid chromatography,Molecular structure Get e-Alerts

Novel ring-coupled reactions of bis(cycloheptatriene)tris(tricarbonyliron) with aryllithium reagents

The reactions of the bis(cycloheptatriene)tris(tricarbonyliron), [(C7H8)2{Fe(CO)3}3] 1, with aryllithium reagents RC6H4Li (R = H, o-, m-, p-CH3, p-OCH3), in diethyl ether at low temperature gave acylmetalate intermediates which following alkylation with Et3OBF4 in aqueous solution at 0 °C led to coupling of the two cycloheptatriene ligands to afford five novel isomerized (bicycloheptatriene)bis(tricarbonyliron)dicarbonyl[ethoxy(aryl)carbene]iron complexes [{(CO)3Fe(C7H7)}2(CO)2FeC(OC2H5)C6H4R] (2, R = H; 3, R = o-CH3; 4, R = m-CH3; 5, R = p-CH3; 6, R = p-OCH3), of which the structure of 2 has been established by a single-crystal X-ray diffraction study. The reaction of complexes 2 or 5 with PPh3 gave the chelated η3-allyliron phosphine adducts [{(CO)3Fe(C7H7)}2(CO)2(PPh3)FeC(OC2H5)C6H4R] (7, R = H; 8, R = p-CH3).

Reactivity of the [(η5-C5Me5)TiCH3][RB(C6F5)3] Complexes Identified as Active Species in Syndiospecific Styrene Polymerization

The reactivity of the alkyl complexes [Cp*Ti(III)(CH3)][RB(C6F5)3] (Cp* = η5-C5Me5; R = CH3, −C6F5) with α-13C-enriched p-chlorostyrene has been investigated by means of ESR spectroscopy in order to gain insight into the chemical structure of the active species in syndiospecific polymerization of styrene and substituted styrenes promoted by “half-titanocene”-based catalysts. Secondary (2,1) polyinsertion of p-chlorostyrene into a Ti(III)−alkyl bond has been observed under polymerization conditions. The role of Cp*TiIIIR+ complexes in syndiospecific styrene polymerization has conclusively been confirmed. Furthermore, the reaction of the 13C-enriched complex [Cp*Ti(13CH3)][RB(C6F5)3] with PMe3 and Al(13CH3)3 has also been investigated by ESR spectroscopy. PMe3 displaces the methylborate anion from the coordination sphere of the Cp*Ti13CH3(μ-13CH3)B(C6F5)3 ion pair and produces the corresponding phosphine adduct Cp*Ti(CH3)(PMe3)2+. In the same manner, the reaction of [Cp*Ti(13CH3)][B(C6F5)4] with Al(13CH3)3 affords the [Cp*Ti(μ-13CH3)3Al(13CH3)]+ adduct. The increase of the intensity of the Ti(III) signals observed in the ESR spectra of these catalytic systems after addition of the monomer has been explained on the basis of the ESR results reported above.

Phosphine Adducts of Monomeric Zinc(bis-phenoxides): Solution and Solid-State Structures of (2,6-Di-tert-butylphenoxide)ZnL Complexes (L = PMePh2 and PCy3)

Phosphine Adducts of Monomeric Zinc(bis-phenoxides): Solution and Solid-State Structures of (2,6-Di-<i>tert</i>-butylphenoxide)ZnL Complexes (L = PMePh₂ and PCy₃)

Syntheses of trirhenium alkoxide clusters in the presence of trimethylphosphine

The THF adduct of rhenium trichloride, Re 3(μ-Cl) 3Cl 6(THF) 3, reacts with trimethylphosphine and NaOPr i to give the chloro-hydride Re 3(μ-OPr i ) 3Cl(H)(OPr) i ) 4(PMe 3) and the dimer {Re 3(μ-OPr i ) 3Cl(OPr i ) 4} 2(μ-Cl) 2 in moderate yields. On the basis of spectroscopic studies and an X-ray crystal structure, the hydride ligand in the chloro-hydride cluster is proposed to occupy a site trans to Cl and cis to PMe 3. The hydride ligand is proposed to originate from isopropoxide β-hydrogen elimination. Ethylene and 2-butyne react with the phosphine-hydride cluster to yield ethyl and 2-butenyl clusters, respectively, and sodium isopropoxide reacts to give Re 3(μ-OPr i ) 3(H)(OPr i ) 5(PMe) 3). The latter compound is more conveniently prepared by reacting PMe 3 with the homoleptic isopropoxide cluster Re 3(μ-OPr i ) 3(OPr i ) 6. In contrast, the analogous reaction of PMe 3 with the homoleptic neopentoxide cluster Re 3(μ-OCH 2Bu t ) 3(OCH 2Bu t ) 6 gives a simple phosphine adduct, Re 3(μ-OCH 2Bu t ) 3(OCH 2Bu t ) 6(PMe 3). The reaction of Re 3(μ-Cl) 3Cl 6(THF) 3 with trimethylphosphine and sodium neopentoxide produces the reduced cluster Re 3(μ-Cl)(μ-OCH 2Bu t ) 4(PMe) 3) 2 in low yield. There are 13 electrons available for Re-Re bonding in the reduced cluster but its structure is not significantly different from similar 12-electron clusters.

An unusually large value of1J(31P,31P) for a solid triphenylphosphine phosphadiazonium cationic complex: determination of the sign ofJfrom 2D spin-echo experiments

Phosphorus-31 NMR spectra of a solid triphenylphosphine phosphadiazonium salt, [Mes*NP-PPh3][SO3CF3], have been acquired at 4.7 and 9.4 T. Analysis of the spectra obtained with magic-angle spinning indicates that the two phosphorus nuclei are strongly spin–spin coupled, [Formula: see text], despite the unusually long P—P separation, rP,P = 2.625 Å. Two-dimensional spin-echo spectra provide convincing evidence that1J(31P,31P) is negative. Semi-empirical molecular orbital calculations at the INDO level support the negative sign for1J(31P,31P). A large span, 576 ppm, is observed for the chemical shift tensor of the two-coordinate phosphorus centre (δ11 = 307 ppm, δ22 = 174 ppm, δ33 = −269 ppm), which is very similar to the value previously reported for the non-coordinated phosphorus centre in the free Lewis acid, [Mes*NP][AlCl4]. The principal components and orientations of the phosphorus shielding tensors of these compounds are compared with those calculated for [HNP]+and its phosphine adduct using the ab initio Gauge-Including Atomic Orbitals method. The phosphorus chemical shift tensor of the triphenylphosphine moiety has a relatively small span of 33 ppm. Key words: spin–spin coupling constants, solid-state NMR,31P NMR, MO calculations, phosphadiazonium cation, P—P bonds.

Reactivity of Tantalum Hydride Aryloxide Complexes toward Organic Isocyanide Reagents

The tantalum monohydride compound [Ta(OC6H3Pri2-2,6)2Cl2(H)(PMe2Ph)2] (1) reacts with organic isocyanides RNC to produce the phosphine adduct η2-iminoformyl complexes [Ta(OC6H3Pri2-2,6)2Cl2{HC(PMe2Ph)NR}] (R = 2,6-diisopropylphenyl (2a), 2,6-dimethylphenyl (2b), tert-butyl (2c)). Compounds 2b,c were only detected spectroscopically as intermediates, while 2a was isolated and reacted with PMe3 to produce the complex [Ta(OC6H3Pri2-2,6)2Cl2{HC(PMe3)NC6H3Pri2-2,6}] (3), which was structurally characterized. The structure of 3 is best described as trigonal bipyramidal about tantalum with a chloride atom and the phosphine adduct of an η2-iminoformyl group occupying axial sites. Important structural parameters for 3 are Ta−N = 1.956(4), Ta−C = 2.210(5), and N−C = 1.421(7) A. Compounds 2a and 3 do not react with a further 1 equiv of 2,6-diisopropylphenyl isocyanide. In contrast 2b reacts with 2,6-dimethylphenyl isocyanide to produce the ylide derivative [Ta(OC6H3Pri2-2,6)3Cl2{RNCHC(PMe2Ph)NR}] (4) (R = C6H3Me2-2,6...

Platinum(II) complexes of the tridentate thioether ligands RS(CH2)3S(CH2)3SR (R = Et, iPr, Ph). Structures of [PtCl (iPrS(CH2)3S(CH2)3SiPr)][BF4], [PtI(PhS(CH2)3S(CH2)2SPh)][BF4], and [Pt(PPh3)(iPrS(CH2)3S(CH2)3SiPr)][BF4]2•CH2Cl2

The tridentate thioether ligands RS(CH2)3S(CH2)3SR (L1, R = Et; L2, R = iPr, L3, R = Ph) were synthesized by nucleophilic addition of thiolate, SR−, to the ditosylate TsO(CH2)3S(CH2)3OTs. The complexes [PtX(Ln)][BF4] were prepared by displacement of 1,5-COD from [PtX2(1,5-COD)] (X = Cl, I) in the presence of one equivalent of AgBF4 and one equivalent of thioether ligand. [PtCl(L2)][BF4] crystallized in the monoclinic space group P21/c with a = 10.409(6), b = 14.180(4), c = 13.726(8) Å, β = 104.49(4)°, V = 1961(2) Å3 and Z = 4. The structure refined toR = 5.62% and Rw = 6.86% for 2121 reflections with F02 &gt; 3σ(Fo2). [PtI(L3)][BF4] crystallized in the monoclinic space group P21/n with a = 13.415(4), b = 12.350(5), c = 14.316(5) Å, β = 107.48(3)°, V = 2262(1) Å3 and Z = 4. The structure refined to R = 4.85% and Rw = 6.33% for 2168 reflections with Fo2 &gt; 3σ(Fo2). In both compounds, the thioether ligand acts as a tridentate chelator occupying three of the four sites of the square-planar Pt(II) complex. Variable temperature 13C{1H} NMR verified that there are three possible stereoisomers for these complexes resulting from inversion at sulphur: meso-A, meso-B, and racemic. Thermodynamic parameters were calculated for the interconversion among isomers of [PtCl(L2)][BF4] by a full line-shape analysis. Removal of chloride ligand from [PtCl(L2)][BF4] with Ag+ in the presence of PPh3 yielded the phosphine adduct [Pt(PPh3)(L2)][BF4]2, which crystallized in the triclinic space group [Formula: see text] with a = 13.266(3), b = 11.315(2), c = 13.970(2) Å, α = 106.04(2)°, β = 84.95(2)°, γ = 86.56(2)°, V = 1999.7(7) Å3 and Z = 2. The structure refined to R = 4.22% and Rw = 5.38% for 4493 reflections with Fo2 &gt; 3σ(Fo2). Unlike the two halide complex structures, which crystallized in the meso-B form, [Pt(PPh3)(L2][BF4]2 crystallized in the racemic form. Key words: tridentate thioether ligand, crystal structure, platinum(II) halide, dynamic NMR spectroscopy.

Reversible adduct formation between phosphines and triarylboron compounds

The acceptor strength of a number of Lewis-acidic fluorinated triarylboron compounds has been established and shown to depend on the amount and position of fluorine substitution. The donor strength of tert-butyl-phosphine has been found to be greater than phosphine towards these acceptor compounds; two series of adducts have been characterised and reversible adduct formation has been demonstrated for some adducts. Crystal structures of the phosphine adducts of tris(pentafluorophenyl)boron and tris(2,6-difluorophenyl)boron have been compared with those of the tert-butylphosphine adducts of tris(pentafluorophenyl)boron and tris(3,4,5-trifluorophenyl)boron to show a correlation between the length and the strength of the adduct bond. Mixing aryl groups in the acceptor compounds has not produced new adducts. The strong acceptor compounds have been found to form unstable adducts with water which act as drying agents ultimately producing arylboric acids; the crystal structure of (2,6-difluoropheny)dihydroxyborane has been determined.

Synthesis and characterization of phosphine adducts of the open zirconocene Zr(C 5H 7) 2

Reactions of either P(CH 3) 2C 6H 5 or dmpe (dmpe = (CH 3) 2PC 2H 4P(CH 3) 2) adducts of ZrCl 4 with four equivalents of KC 5H 7 lead to the formation of the respective 16 or 18 electron mono(ligand) adducts of the open zirconocene Zr(C 5H 7) 2. Both complexes were found to exist in the expected symmetric conformations, as confirmed for the dmpe complex by a single crystal X-ray diffraction study.

The reaction of the P 2N 2 Schiff base ligand en=P 2 with MI 2 salts and the reaction of the tetraiodine adduct of en=P 2 with unactivated coarse grain metal powders: a comparative study (en=P 2= N, N′-bis[( o-diphenylphosphino)benzylidene]ethylene-diamine; M=Mn, Co and Ni)

The reaction of the N 2P 2 donor set Schiff base ligand en=P 2 with metal salts MI 2 (M=Mn, Co and Ni) produces compounds of stoichiometry M(en=P 2)I 2. Single crystal X-ray diffraction studies have shown the nickel complex to be five-coordinate [Ni(en=P 2)I]I and to have a square pyramidal structure. This complex appears to exist in a spin-crossover state, μ eff=2.35 μ B. The analogous cobalt complex has been shown by X-ray powder diffraction to be isostructural with the nickel complex, but is low spin, μ eff=2.40 μ B. Reaction of en=P 2 with two equivalents of diiodine in dry diethyl ether produces an adduct of stoichiometry (en=P 2)I 4. Solution 31P{H} NMR studies in CDCl 3 indicate one phosphorous environment, δ=53.4 ppm. Addition of two further equivalents of diiodine to this compound in CDCl 3 results in no change in the 31P chemical shift, implying that (en=P 2)I 4 exists as the ionic [(en=P 2I 2] 2+2I − in CDCl 3 solution. The solid state Raman spectrum of (en=P 2)I 4 shows a strong band at 154 cm −1 which is assigned to ν(PI). Another band is observed at 111 cm −1, which has been tentatively assigned to ν(II) indicating that the compound may exist as a molecular charge transfer adduct in the solid state. This tetraiodophosphorous adduct reacts with Mn, Co and Ni coarse grain metal powders to form compounds of stoichiometry M(en=P 2)I 4. The cobalt and nickel complexes have been shown to be isostructural by X-ray powder diffraction methods. Bands in the UV-Vis spectrum at ≈293 nm and at 364 nm indicate the presence of the I 3 − ion, which we believe indicates that these compounds adopt a five coordinate geometry analogous to the [M(en=P 2)I]I compounds of [M(en=P 2)I]I 3. This is further supported by the room temperature magnetic moment of [Co(en=P 2)I]I 3 of 3.8 μ B consistent with a high spin five-coordinate cobalt(II) centre which is in complete contrast to that observed for [Co(en=P 2)I]I. This further highlights the ability of dihalogen adducts of tertiary phosphines to react with coarse grain unactivated metal powders to generate products not attainable by conventional means.

Reaction of Rh 2( μ2-O 2CCH 3) 3[ μ2-(C 6H 4)PMePh](HO 2CCH 3) 2 with triphenylphosphine: rearrangement of the metalated PMePh 2 ligand and formation of a compound with a diphenylphosphinomethanide group in (P,C) coordination; crystal structure of [Rh 2( μ2-O 2CCH 3) 2{ μ2-(CH 2)PPh 2}- { μ2-(C 6H 4)PPh 2}(PPh 3)]·2CH 2Cl 2

The reaction of [Rh 2( μ 2-O 2CCH 3) 3{ μ 2-(C 6H 4)PMePh}] ( 1) in CHCl 3 with one mole of PPh 3 gives the two phosphine monoadducts, which are in rapid equilibrium above −40 °C. After 6 h at room temperature this mixture gives [ Rh 2(μ 2- O 2 CCH 3 2{μ 2-( C 6 H 4) PMePh}{μ 2-( C 6 H 4) PPh 2}]( HO 2 CCH 3) 2 ( 3) , a doubly metalated compound with a head-to-head configuration. 1 reacts with two moles of PPh 3, forming the bis-adduct 1.P 2, which at 10 °C gives a mixture 3, in the form of its phosphine adduct 3.P, and [Rh 2( μ 2-O 2CCH 3) 2{ μ 2-(CH 2)PPh 2}{ μ 2- (C 6H 4) PPh 2}(PPh 3)] ( 2). It is confirmed that 3.P is not the kinetic product in the reaction from 1.P 2 to 2. The structure of [Rh 2( μ 2-O 2CCH 3) 2{ μ 2-(CH 2)PPh 2}{ μ 2-(C P 6H 4) PPh 2} (PPh 3)]·2CH 2Cl 2 has been determined by X-ray diffraction: M r = 1216.55, monoclinic, space group P2 1/c, a=19.930(8), b=15.29(2), c=16.84(2) A ̊ , β=90.14(9)°, V=5129(9) A ̊ 3, Z=4, D c =1.58 g cm −3 , Mo Kα radiation (graphite monochromator, λ=0.71073 A ̊ ), μ (Mo K α)=9.80 cm −1, F(000)=2464, T=200 K. The final conventional R factor was 0.061 for 4749 ‘observed’ reflections. The compound contains an orthometalated triphenylphosphine and a diphenylphosphinomethanide group bridging the two rhodium atoms. The two ligands are in a head-to-head configuration. Two bridging acetate groups and one axial PPh 3 complete the coordination around the rhodium atoms. The RhRh bond distance is 2.532(2) Å.

Functional group reductions with Lewis base adducts of gallane

Tertiary amine and tertiary phosphine adducts of gallane, L·GaH 3 (L = Me 3N, quinuclidine, (C 6H 11) 3P), reduce a variety of unsaturated functional groups with a selectivity different to that observed for similar alane adducts.

Photochemical reactions of several adducts of metalladithiolenes and metalladithiazoles---dissociation and rearrangement--

The addition products of metalladithiolene and metalladithiazole complexes undergo interesting photochemical dissociation reactions accompanied by rearrangement. Three examples are discussed. Upon irradiation with a medium pressure mercury lamp, the quadicyclane adducts of cobaltadithiolene and rhodiadithiolene dissociate to the free metalladithiolenes and norbornadiene accompanied by the skeletal rearrangement in the hydrocarbon moieties. The tributylphosphine adduct of a cobaltadithiolene eliminates photochemically the coodinated phosphine via the attack of singlet oxygen. In the photoreaction with 254 nm light, the phosphine adduct itself acts as a triplet sensitizer to produce singlet oxygen. The DMAD adducts of 1,2,5-cobaltadithiolene and 1,2,5,3-cobaltadithiazole behave differently upon irradiation: DMAD adduct of the cobaltadithiolene eliminates selectively the alkyne moiety which bridges between Co and S, while DMAD adduct of the cobaltadithiazole eliminates carbonitrile to give the cobaltadithiolenes.

ChemInform Abstract: Tertiary Phosphine Adducts of Mixed Halogens, R3PIBr; Synthesis and Structure in the Solid State and Solution.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Reactions of carbon monoxide with phosphine adducts of Nb(2,4-C7H11)2: spontaneous reduction of niobium(I) complexes

Reactions of carbon monoxide with phosphine adducts of Nb(2,4-C7H11)2: spontaneous reduction of niobium(I) complexes

Phosphine adducts of the open metallocenes of zirconium, hafnium, niobium, and molybdenum: syntheses, structures, and reactions with carbon monoxide

Phosphine adducts of the open metallocenes of zirconium, hafnium, niobium, and molybdenum: syntheses, structures, and reactions with carbon monoxide