Effects of Side-Chain Substituents in Benzo-15-Crown-5 on Lithium Extraction

Chloroform–water extraction systems have been studied using crown-ethers as extracting agents, namely: benzo-15-crown-5 (B15C5), 2,3-naphtho-15-crown-5 (N15C5), 4′-nitro-benzo-15-crown-5 (NO₂B15C5), 4′-tert-butyl-benzo-15-crown-5 (TBB15C5), and 4′-acetyl-benzo-15-crown-5 (AcB15C5). Extraction isotherms of these systems have been obtained, and an attempt made to elucidate the effect of the structure of extracting agent on extraction characteristics. IR-spectroscopic studies have been performed for selected crown-ethers and their complexes in crystalline form and in chloroform solutions, namely, for N15C5, NO₂B15C5, AcB15C5, and B15C5. The complexes LiN15C5H₂OClO₄ (1), LiN15C5H₂OI (2), LiNO₂B15C5H₂OI (3), LiAcB15C5H₂OI (4), and LiTBB15C5H₂OI (5) have been isolated for the first time and characterized by IR spectroscopy. Single-crystal X-ray data have been obtained for complexes 1–3.     

Synthesis and properties of copper(II) complexes with a chiral dioxatetraazamacrocyclic ligand based on a natural monoterpene, (+)-3-carene

The copper(II) compounds [CuL](NO₃)₂ · H₂O (I), [CuL](ClO₄)₂ · H₂O (II), CuLCl₂ · 3H₂O (III), and CuLBr₂ · 4H₂O (IV), where L is a chiral dioxatetraazamacrocyclic ligand based on the natural monoterpene (+)-3-carene, have been synthesized. According to IR and EPR spectroscopy, L acts as a tetradentate chelating ligand coordinated through the N atoms of the NH and C=N groups. The NO ₃ ^? anions in I and the ClO ₄ ^? anions in II are outer-sphere. I and II have a planar coordination core CuN₄, III has a CuN₄ClO coordination core, and IV has a CuN₄Br₂ coordination core.     

Copper(II) Complexes with Chiral Ligands Containing Fragments of Monoterpenoids and Amino Acid Esters

Complexes [CuL¹Cl₂] (I), [CuL²Cl₂] · EtOH (II), and Cu₂L³Cl₄ (III) containing esters of the N-derivatives of optically active amino acids based on (+)-3-carene (L¹, L²) and (?)-α-pinene (L³) are synthesized. The crystal and molecular structures of compounds I and II are determined by X-ray diffraction analyses (CIF files CCDC nos. 1560071 (I), 1560072 (II)). The crystal structure of compound I consists of mononuclear complex molecules. In the structure of compound II, the unit cell contains two crystallographically independent molecules of mononuclear complex [CuL²Cl₂] and two EtOH molecules. Ligands L¹ and L² perform the tridentate-chelating function by the N atoms of the NH and NOH groups and by the O atom of the C=O group. In compounds I and II, the coordination polyhedra Cl₂N₂O of the Cu atoms are trigonal bipyramid. According to the data of IR and electronic spectroscopy, binuclear complex III has similar coordination polyhedra. The experimental values of μ_eff for compounds I, II, and III at 300 K are 1.93, 1.88, and 2.71 μB. For complex III, the μ_eff(T) dependence in a range of 2–300 K indicates a weak ferromagnetic exchange interaction.     

New organophosphorus compounds containing nicotinamide: synthesis,structure and DFT calculations

Novel organophosphorus compounds, containing Nicotinamide, with formula C₅H₄NC(O)NHP(O)R₂, R=Cl (1), OH (2), N(C₂H₅)₂ (3), N(C₃H₇)₂ (4), N(n-C₄H₉)₂ (5), NHC₃H₅ (6), NHC₅H₉ (7), were synthesized and characterized by ¹H, ¹³C, ³¹P, NMR, IR, spectroscopy and elemental analysis. Single crystal structures of 3 7 were determined by X-ray crystallography. ¹HNMR spectra of compounds 2, 3, 6–8 demonstrated interesting long-range coupling constant, ⁿ J _P,H (n = 5 7). Crystallographic data revealed that in both molecules 3 and 7, the phosphoryl and the carbonyl groups have anti-configurations and the phosphorus atoms in these structures have distorted tetrahedral configuration. All the hydrogen bonds and electrostatic interactions make a three dimensional polymeric network for both 3 and 7. Interestingly, two independent conformers were detected in the unit cell of compound 7. The two conformers of the title compound can be observed in a solid phase but only one compound defined in a solution. These two conformers are connected to each other by a short contact, N (amine)···H–C (pyridine) with 2.626 Å distance. The molecular geometry of 7 was calculated by DFT/B3LYP (6–31+G**) quantum chemical calculations. The computational optimized geometric parameters and vibrational frequencies showed a good agreement with the experimental results, considering reasonable variations arising from the differences between solid and gaseous phases. Theoretical calculations revealed that the more stable conformer of the title compound is conformer 1 with the energy of ?1335.723996 a.u., which is about 1.17 kcal/mol lower than the energy of conformer 2.     

Cobalt(III) complexes with biguanide derivatives: Synthesis,structures, and antiviral activity

Three Co(III) complexes with biguanide derivatives [Co(NH₂C(=NH)NHC(=NH)NR¹R²)₃]Cl₃ (R¹R² = Me₂ (I), Et₂ (II), and H^sBu (III)) were obtained and characterized by elemental analysis, IR spectroscopy, and electronic absorption spectroscopy. Structure III was confirmed by X-ray diffraction (CIF file CCDC no. 1401783). Complexes I–III and [M(SC(NH₂)₂)₄]Cl₂ (M = Pd, Pt, and [Co(En)₃]Cl₃) were tested for in vitro antiviral activity against the A/California/07/09 (H1N1pdm09) influenza virus. The best results were achieved with complex III and both thiourea complexes.     

Crown-substituted Sc(III) phthalocyaninates: Synthesis and spectral properties

The scandium(III) complexes with tetra(15-crown-5)phthalocyanine [Sc(R₄Pc)₂]^·0 (I) and Sc(R₄Pc) · OAc (II) have been synthesized by condensation of Sc³⁺ with phthalocyanine H₂R₄Pc (4,5,4′,5′,4″,5″,4?,5?-tetrakis(1,4,7,10,13-pentaoxatridecamethylene)phthalocyanine). Compounds I and II have been characterized by spectral methods: electronic absorption spectroscopy, MALDI-TOF MS, IR spectroscopy, and ¹H NMR. The redox properties of I and the photoluminescent properties of II have been studied.     

Tetraphenylantimony perrhenate and tetraphenylantimony chlorate: Syntheses and structures

The reaction of tetraphenylantimony chloride with sodium perrhenate or potassium chlorate yields tetraphenylantimony perrhenate (I) and tetraphenylantimony chlorate (II), respectively. Complex I was also synthesized from pentaphenylantimony and triphenylantimony diperrhenate in toluene. According to X-ray diffraction, crystals I and II consist of almost regular tetrahedral tetraphenylstibonium cations (CSbC, 109.4(2)°–109.5(7)° in I and 109.1(1)°–109.6(1)° in II) and [ReO₄]^? (OreO, 107.6(3)°–113.3(5)°) and [ClO₃]^? (OClO, 96.3(9)°, 116.4(5)°) anions, respectively. The average Sb-C bond lengths (2.094(3) Å in I, 2.097(2) Å in II) are close to the sum of the covalent radii of the Sb and C atoms. The average distances Re-O in complex I (1.672(4) Å) and Cl-O in complex II (1.315 Å) correspond to multiple bonds.     

Syntheses,structures and catalytic activities of molybdenum carbonyl complexes based on pyridine-imine ligands

Thermal treatment of pyridine imines [C₅H₄N-2-C(H)=N-C₆H₄-R] [R = H (1), CH₃ (2), OMe (3), CF₃ (4), Cl (5), Br (6)] with Mo(CO)₆ in refluxing toluene provided six novel mononuclear molybdenum carbonyl complexes of the type [(η²-2-C₅H₄N)CH=N(C₆H₄-4-R)]Mo(CO)₄ [R = H (7); CH₃ (8); OMe (9); CF₃ (10); Cl (11); Br (12)]. All of these complexes were separated by chromatography and fully characterized by elemental analysis, IR, and NMR spectroscopy. The crystal structures of complexes 7, 8 and 10 were determined by X-ray crystal diffraction analysis. In addition, the catalytic performance of these complexes was also tested, and it was found that these complexes had obvious catalytic activity on Friedel–Crafts reactions of aromatic compounds with a variety of acylation reagents.     

Mesitylenesulfonic acid dihydrate: structure and proton conductivity

The molecular and crystal structure of single-crystalline mesitylenesulfonic acid dihydrate (1) was determined by X-ray diffraction and IR spectroscopy. According to X-ray diffraction data, water molecules in the crystal structure form H₅O₂ ⁺ cations stabilized by an intracationic hydrogen bond with a length of 2.45(1) Å. The formation of the asymmetric H₅O₂ ⁺ cation was confirmed by IR spectroscopy. The crystallographic nonequivalence of the water molecules results in a shift of the bridging proton from the midpoint of the strong hydrogen bond in the cation toward one of the water molecules. The proton conductivity of compound 1 was measured by impedance spectroscopy. Dihydrate 1 is completely dehydrated upon prolonged storage in a dry argon glove box and undergoes the transition to the dielectric state. Compound 1 is stable in the humidity range of 32–66 rel.%. The conductivity of dihydrate 1 is (2.4±0.3) · 10^?5 Ohm^?1 cm^?1 at 298 K, E _a = 0.21±0.01 eV.     

Supramolecular homobimetallic <Emphasis Type="Italic">bis</Emphasis>-diorganotin(IV) complexes of ditopic oxygen nitrogen donor ligand: synthesis,spectroscopic characterization,crystal structure and biological screening

Six new homobimetallic bis-diorganotin(IV) complexes: [Me₂Sn]₂L (1), [Et₂Sn]₂L (2), [n-Bu₂Sn]₂L (3), [Ph₂Sn]₂L (4), [Oct₂Sn]₂L (5) and [n-BuClSn]₂L (6) (H ₄ L=N¹′, N⁶′-bis(2-hydroxybenzylidene)adipodihydrazide) have been synthesized and structurally characterized by means of elemental analysis, mass spectroscopy, FT-IR, NMR (¹H, ¹³C{¹H}, ¹¹⁹Sn) and single-crystal X-ray diffraction. Spectroscopic studies indicate coordination of the ligand to the diorganotin(IV) moieties via iminolic oxygen, nitrogen and phenolic oxygen atoms generating pentacoordinated tin centers. Single-crystal X-ray analysis of (1) revealed homobimetallic nature of complex with dimethyltin moieties oriented in trans-conformation. The ligand is non-planar with each Sn atom in a distorted square pyramidal coordination geometry. Packing diagrams suggest the essential role of C–H^…N and C–H^…O interactions in generating supramolecular assembly. The ligand and complexes were screened for in vitro antimicrobial activity and cytotoxicity. Compound (4) exhibits highest cytotoxicity.     

New copper(II) coordination compounds with 1,3-bis(5-(pyridin-2-yl)-1,2,4-triazol-3-yl)propane

Two new copper(II) complexes with 1,3-bis(5-(pyridin-2-yl)-1,2,4-triazol-3-yl)propane (H₂L), [Cu₂(HL)Cl₃] · H₂O (I) and [Cu(H₂L)](ClO₄)₂ (II), were described. The compounds were characterized by elemental analysis, IR spectroscopy, and magnetochemical data. According to X-ray diffraction data (CIF files CCDC nos. 1497511 (I), 1497512 (II)), complex I is binuclear and the metal cations are bound by the nitrogen atoms of the triazole ring and by the chloride anion. Complex II is mononuclear. Analysis of the temperature dependence of the magnetic susceptibility of I attests to the antiferromagnetic coupling of paramagnetic centers (–2J = 18 cm^–1). Exchange channels are analyzed by means of density functional theory (B3LYP/6-311G(d)) using the broken symmetry approach.     

Synthesis,crystal structure,and luminescent property of two novel Zn/Co(II) coordination polymers with a linear bis-imidazole and dicarboxylate ligands

The linear linker 1,3-bis(2-methylimidazolyl)propane (Bmip) has been used to construct two new coordination polymers with Zn²⁺ and Co²⁺ ions and carboxylate donor ligand viz., 4,4’-oxydibenzoic acid (H₂Oba). Compounds formed hydrothermally are [Zn(Bmip)(Oba)] _n (Ι), [Co(Bmip)(Oba)] _n (II). Complexes Ι and II have been characterized by single crystal X-ray diffraction (CIF files CCDC nos. 1033354 (I), 1001813 (II)), IR spectroscopy, thermogravimetry, elemental analysis and powder X-ray diffraction. Single crystal X-ray analysis revealed that complexes Ι and II are isostructural, which exhibit 2D 4⁴-sql net. And the adjacent 4⁴-sql net are further inforced through weak noncovalent C–H···π and H-bonding to form a 3D supramolecular framework. Furthermore, the photoluminescence property of complexes Ι and II in the solid state at room temperature was also investigated.     

Effect of the air humidity on the proton conductivity of some aminobenzenesulfonic acids

Effects of environment conditions (humidity and temperature) on the proton conductivity of aminobenzenesulfonic acids: 2-amino-(orthanilic) acid (I), 3-amino-(metanilic) acid (II), 4-amino-(sulfanilic) acid (III), their general formula NH₂C₆H₄SO₃H, and 3-amino-4-hydroxobenzenesulfonic acid (IV) [NH₂(OH)C₆H₃SO₃H), as well as (for sake of comparison) inorganic aminosulfonic acid [sulphamic acid (NH₂SO₃H)] (V) are studied. All above-listed compounds are zwitter-ions: they contain a fragment NH ₃ ⁺ SO ₃ ^? . The presence of this structural fragment affects the thermal stability of the compounds; according to the mass-spectrometry analysis data, the decomposition of the SO₃-fragment begins at the following temperatures: (I) ?339, (II) ?370, (III) ?320, (IV) ?278, and (V) ?220°C. It is shown that the increase of the environment relative humidity up to 95% results in the increase of the aminobenzenesulfonic acids proton conductivity from 10^?9–10^?8 to 10^?5 S cm^?1; sulphamic acid, to 10^?4 S cm^?1. At that, the amount of adsorbed water does not exceed 0.2 moles per 1 sulfo group in all cases. The conductance activation energy equals 0.2 eV at a relative humidity of 95%.     

Synthesis and structure of bischelate gallium complexes (dpp-bian)Ga(acac) and (dpp-bian)Ga(2,2´-bipy) (dpp-bian is 1,2-bis[(2,6-diisopropylphenyl)imino]acenaphthene)

A reaction of digallane [(dpp-bian)Ga—Ga(dpp-bian)] (1) (dpp-bian is the 1,2-bis[(2,6-disopropylphenyl)imino]acenaphthene) with one equivalent of I₂ leads to oxidation of (dpp-bian)^2– in compound 1 to (dpp-bian)–and gives [(dpp-bian)GaI—GaI(dpp-bian)] (2). In the reaction of compound 2 with two equivalents of (acac)Na, not only exchange of the iodide and acetylacetonate ions takes place, but also a transfer of electrons from the metal—metal bond to dpp-bian with the formation of the complex [(dpp-bian)Ga(acac)] (3), in which the dpp-bian ligand is a dianion. A reaction of digallane 1 with 2,2´-bipyridyl at 200 °C in toluene in a sealed tube leads to the reduction of 2,2´-bipyridyl and gives the complex [(dpp-bian)Ga(bipy)] (4), which contains two different chelate redox-active ligands. The new compounds were characterized by IR (3, 4), NMR (3), and ESR spectra (4), the structures of both derivatives were established by X-ray diffraction.     

Cobalt(II) and copper(II) complexes with chiral pyrazolylquinoline,a derivative of terpenoid (+)-3-carene. Catalytic activity in ethylene polymerization reaction

Coordination compounds [CoLCl₂] (I), [CuLCl(NO₃)] (II), CuL(NO₃)₂ (III), and CuLCl₂ (IV) (where L is a chiral pyrazolylquinoline—a derivative of terpenoid (+)-3-carene) were synthesized. X-ray diffraction data showed that crystal structures I and II are built of mononuclear acentric molecules. In the molecule of complex I, the Co₂₊ ion coordinates two N atoms of bidentate cycle-forming ligand L and two Cl atoms. The coordination polyhedron of Cl₂N₂ is a distorted tetrahedron. For complex I, μ_eff = 4.50 μ_B, which corresponds to a high-spin configuration d ⁷. In the molecules of II(1), II(2) (which are diastereoisomers of complex II), each Cu²⁺ ion coordinates two N atoms of bidentate cycle-forming ligand L, the Cl atom, and two O atoms of bidentate cyclic NO ₃ ^? ion. The ClN₂O₂ coordination polyhedra are tetragonal pyramids with different degrees of distortion. The structure of complex II consists of supramolecular clusters, i.e., isolated chains incorporating the molecules of II(1) and II(2). The values of μ_eff for II–IV correspond to the d ⁹ configuration. The results of EPR and IR study suggest that complex III contains the O₄N₂ polyhedron, whereas complex IV contains the Cl₂N₂ polyhedron. Complexes I and IV were found to show a high catalytic activity in ethylene polymerization reaction.     

Bimetallic Fe–Cu Carbido Carbonyl Clusters Obtained from the Reactions of [Fe<Subscript>4</Subscript>C(CO)<Subscript>12</Subscript>{Cu(MeCN)}<Subscript>2</Subscript>] with N-Donor Ligands

The reaction of [Fe₄C(CO)₁₂{Cu(MeCN)}₂] (1) with 3 equivalents of L–L (phen or Me₂phen) affords [Cu(L–L)₂][Fe₄C(CO)₁₂{Cu(L–L)}] (L–L = phen, 2; Me₂phen, 3) in good yields. These are protonated by strong acids resulting in [HFe₄C(CO)₁₂{Cu(L–L)}] (L–L = phen, 4; Me₂phen, 5). The reaction may be reversed with bases, resulting in the quaternary ammonium salts [NR₄][Fe₄C(CO)₁₂{Cu(phen)}] (6). 4 and 5 react with a slight excess of L–L resulting in the elimination of copper in the form of [Cu(L–L)₂]⁺ and formation of the previously reported [HFe₄C(CO)₁₂]^? homometallic cluster. Conversely, the reaction of 1 with a monodentate N-ligand such as quinoline, even if used in large excess, results in the substitution product [Fe₄C(CO)₁₂{Cu(quinoline)}₂] (8), which is then transformed into [Cu(Me₂phen)₂] [Fe₄C(CO)₁₂{Cu(quinoline)}] (9) after reaction with Me₂phen. By using the anionic cluster [Fe₅C(CO)₁₄{Cu(MeCN)}]^? instead of the neutral 1, only substitution has been observed by using both phen and quinoline, resulting in [Fe₅C(CO)₁₄{Cu(phen)}]^? (10) and [Fe₅C(CO)₁₄{Cu(quinoline)}]^? (11), respectively. Finally, the reaction of 1 with [Ru(tpy)(bpy)(N₄C-C₆H₄-CN)]Cl affords crystals of [Fe₄C(CO)₁₂Cu₂Cl{Ru(tpy)(bpy)(N₄C-C₆H₄-CN)}] (12). All compounds 2-12 have been characterized by a combination of spectroscopic (IR, NMR) and crystallographic methods. All these clusters may be viewed as composed by a butterfly [Fe₄C(CO)₁₂]^2? core bonded to Cu(I) fragments and/or H⁺ ions.     

Synthesis and catalytic activity of rhenium carbonyl complexes containing alkyl-substituted tetramethylcyclopentadienyl ligands

A series of six alkyl-substituted tetramethylcyclopentadienyl mononuclear metal carbonyl complexes [(η ⁵-C₅Me₄R)Re(CO)₃] [R = allyl (1), i-Pr (2), n-butyl (3), t-butyl (4), benzyl (5), CH(CH₂)₄ (6)] have been synthesized by treating the corresponding ligands (C₅Me₄R) [R = allyl, i-Pr, n-butyl, t-butyl, benzyl, CH(CH₂)₄] with Re₂(CO)₁₀ in refluxing xylene. The six new complexes were characterized by elemental analysis, IR, ¹H NMR and ¹³C NMR spectroscopy. The crystal structures of all six complexes were determined by X-ray crystal diffraction analysis, showing that they have similar molecular structures, being mononuclear carbonyl complexes. In each of these complexes, the Re atom is η ⁵ -coordinated to the cyclopentadienyl ring. Complexes 1–5 have significant catalytic activity in Friedel–Crafts reactions of aromatic compounds with alkylation reagents. Compared with traditional catalysts, these mononuclear rhenium carbonyl complexes have obvious advantages such as lower amounts of catalyst, mild reaction conditions and environmentally friendly chemistry.     

Improved synthesis and low-temperature performance of a series of saturated α-branched fatty acids

Five saturated α-branched fatty acids, also known as Guerbet acids, including α-propylhexyl acid (G ₁ ), α-butylhexyl acid (G ₂ ), α-propyloctyl acid (G ₃ ), α-butyloctyl acid (G ₄ ), and α-hexyloctyl acid (G ₅ ), were synthesized in high yields by four-step reaction. Colorless, almost odorless, and oily products were obtained with high purity, whose structures were confirmed by GC, ¹H/¹³C NMR, and ESI–MS characterization. G ₁ , G ₃ , and G ₄ had pour points lower than ?60 °C, while G ₂ and G ₅ showed higher pour points (?42 °C and 6 °C, respectively) because of their molecular symmetry. Considering the low-temperature properties, G ₁ , G ₃ , G ₄ , and even G ₂ held great potential applications in the lubricant and oilfield.     

The conformational spaces of dinaphthyl ketones,dinaphthyl thioketones,and dinaphthyl diazomethanes: 1-substituted naphthalenes versus 2-substituted naphthalenes

1,1′-Dinaphthyl ketone (15), 1,2′-dinaphthyl ketone (18), 2,2′-dinaphthyl ketone (19), 1,1′-dinaphthyl thioketone (16), 1,2′-dinaphthyl thioketone (20), 2,2′-dinaphthyl thioketone (21), 1,1′-dinaphthyldiazomethane (17), 1,2′-dinaphthyldiazomethane (22), and 2,2′-dinaphthyldiazomethane (23) have been synthesized. Ketone 15 has been prepared from di(1-naphthyl)methanol; ketone 18 has been prepared by a Friedel–Crafts acylation of naphthalene with 2-naphthoyl chloride; ketone 19 has been prepared by a Grignard reaction of 2-naphthylmagnesium bromide with 2-naphthoyl chloride. Thioketones 16, 20, and 21 have been prepared by reactions of the corresponding ketones 15, 18, and 19 with Lawesson’s reagent. The diazomethane derivatives 17, 22, and 23 have been prepared by the HgO oxidation of the respective hydrazones 25, 27, and 28 (prepared from the respective thioketones 16, 20, and 21). The crystal and molecular structures of ketones 15, 18, and 19 and of thioketone 16 have been determined. A variety of conformations in the crystal structures is noted: 1Z,1′Z (15), 1E,1′Z (16), 1E,2′E (18), 2Z,2′Z (19). The NMR experiments have demonstrated the downfield shifts of the protons peri to the carbonyl and the thiocarbonyl groups in 15, 16, and 18, but not in 20. A systematic DFT study (B3LYP/6-31G(d)) of the conformational spaces of 15–23 and their ¹H and ¹³C NMR chemical shifts has been performed. In each series of constitutional isomers, the order of stabilities is 2,2′-(NA)₂C=X > 1,2′-(NA)₂C=X > 1,1′-(NA)₂C=X. The decrease in the stabilities of 1-naphthyl derivatives relative to 2-naphthyl derivatives is attributed to the increased overcrowding and the increased twist angles in 1-naphthyl derivatives. The increased stabilization of E-conformations with the increase of the radius of a heteroatom at C⁹ due to the steric reasons is noted. The DFT calculations satisfactorily describe the X-ray conformations of 15, 16, 18, and 19.     

Hydroamination of alkynes with aromatic amines catalyzed by digallane (dpp-bian)Ga—Ga(dpp-bian)

Digallane (dpp-bian)Ga—Ga(dpp-bian) (1) (dpp-bian is the 1,2-bis[(2,6-diisopropylphenyl)imino]acenaphthene) catalyzes the addition of 4-chloroaniline to some terminal alkynes RC≡CH (R = Buⁿ, Ph, 4-MeC₆H₄). The reaction orders in each of the substrates were found for the reaction of phenylacetylene with 4-chloroaniline catalyzed by compound 1. The reaction of compound 1 with phenylacetylene in a molar ratio of 1: 10 led to 1-[N-(2,6-diisopropylphenyl)imino]-2-(1-phenylethylidene)acenaphthene (5) and the compound [C₁₂H₆(NC₆H₃Pr₂ ⁱ)(PhC=CH₂)(PhC=CH)]Ga(C≡CPh)₂ (6). The reaction of digallane 1 with phenylacetylene and aniline in a stoichiometric ratio of 1: 2: 2 gave bis-anilide (dpp-bian)-Ga[N(H)Ph]₂ (7) in 40% yield. The compound (PhC≡C)₃Ga·THF (9) was obtained by the reaction of three equivalents of sodium phenylacetylide (prepared in situ from phenylacetylene and sodium) with one equivalent of GaCl₃ in tetrahydrofuran. Compounds 5—7 and 9 were characterized by IR spectroscopy, ¹H NMR spectroscopy was used to characterize products 5, 6, and 9, whereas EPR spectroscopy was used for amide 7. The structures of compounds 5—7 and 9 were determined by single crystal X-ray diffraction analysis.