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Journal articles on the topic 'P-N ligands'

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Published: 4 June 2021

Last updated: 25 May 2024

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1

Meyer, Marco, Fabian Brunner, Alessandro Prescimone, Edwin C. Constable, and Catherine E. Housecroft. "Chimera Diimine Ligands in Emissive [Cu(P^P)(N^N)][PF6] Complexes." Inorganics 8, no. 5 (May 12, 2020): 33. http://dx.doi.org/10.3390/inorganics8050033.

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The syntheses and characterizations of the chelating ligand 6-chloro-6′-methyl-2,2′-bipyridine (6-Cl-6′-Mebpy) and of the copper(I) compounds [Cu(POP)(6-Cl-6′-Mebpy)][PF6] and [Cu(xantphos)(6-Cl-6′-Mebpy)][PF6] (POP = bis(2-(diphenylphosphanyl)phenyl)ether and xantphos = 4,5-bis(diphenylphosphanyl)-9,9-dimethyl-9H-xanthene) are described. The single crystal structures of both complexes were determined; the copper(I) ion is in a distorted tetrahedral environment and in [Cu(xantphos)(6-Cl-6′-Mebpy)][PF6], the disorder of the 6-Cl-6′-Mebpy ligand indicates there is no preference of the ‘bowl’-like cavity of the xanthene unit to host either the methyl or chloro-substituent, consistent with comparable steric effects of the two groups. The electrochemical and photophysical properties of [Cu(POP)(6-Cl-6′-Mebpy)][PF6] and [Cu(xantphos)(6-Cl-6′-Mebpy)][PF6] were investigated and are compared with those of the related compounds containing 6,6′-dichloro-2,2′-bipyridine or 6,6′-dimethyl-2,2′-bipyridine ligands. Trends in properties of the [Cu(P^P)(N^N)]+ complexes were consistent with 6-Cl-6′-Mebpy behaving as a combination of the two parent ligands.

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2

Munzeiwa, Wisdom A., Bernard Omondi, and Vincent O. Nyamori. "Architecture and synthesis of P,N-heterocyclic phosphine ligands." Beilstein Journal of Organic Chemistry 16 (March 12, 2020): 362–83. http://dx.doi.org/10.3762/bjoc.16.35.

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Diverse P,N-phosphine ligands reported to date have performed exceptionally well as auxiliary ligands in organometallic catalysis. Phosphines bearing 2-pyridyl moieties prominently feature in literature as compared to phosphines with five-membered N-heterocycles. This discussion seeks to paint a broad picture and consolidate different synthetic protocols and techniques for N-heterocyclic phosphine motifs. The introduction provides an account of P,N-phosphine ligands, and their structural and coordination benefits from combining heteroatoms with different basicity in one ligand. The body discusses the synthetic protocols which focus on P–C, P–N-bond formation, substrate and nucleophile types and different N-heterocycle construction strategies. Selected references are given in relation to the applications of the ligands.

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3

Takahashi, Shintaro, Kazuki Nakaya, Akihiko Ishii, and Norio Nakata. "[N,N′-Di-tert-butyl-P,P-diphenylphosphinimidic Amidato-κN,κN′]chlorosilicon-κSi-tetracarbonyliron." Molbank 2022, no. 3 (August 25, 2022): M1433. http://dx.doi.org/10.3390/m1433.

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The title complex {[Ph2P(tBuN)2](Cl)Si:->Fe(CO)4} (2) was synthesized via the reaction of chlorosilylene [Ph2P(tBuN)2]SiCl (1), supported by an iminophosphonamide ligand with Fe(CO)5 in THF. The molecular structure of 2 was fully characterized by NMR (1H, 13C, 29Si, and 31P) and IR spectroscopies, as well as single-crystal X-ray diffraction (SCXRD) analysis. In the SCXRD analysis of 2, the silylene ligand was located in the axial positions of the coordination sphere of the central iron atom and other sites were occupied by carbonyl ligands.

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4

Rozanov, I. A., D. A. Murashov, L. Ya Medvedeva, V. I. Moiseev, and L. L. Maduskina. "New P,N-Cyclic Ligands." Phosphorus, Sulfur, and Silicon and the Related Elements 51, no. 1-4 (September 1990): 472. http://dx.doi.org/10.1080/10426509008040996.

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5

Nohara, Isaak, Alessandro Prescimone, Catherine Housecroft, and Edwin Constable. "Softening the Donor-Set: From [Cu(P^P)(N^N)][PF6] to [Cu(P^P)(N^S)][PF6]." Inorganics 7, no. 1 (January 18, 2019): 11. http://dx.doi.org/10.3390/inorganics7010011.

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We report the synthesis and characterization of [Cu(P^P)(N^S)][PF6] complexes with P^P = bis(2-(diphenylphosphino)phenyl) ether (POP) or 4,5-bis(diphenylphosphino)-9,9- dimethylxanthene (xantphos) and N^S = 2-(iso-propylthio)pyridine (iPrSpy) or 2-(tert-butylthio)pyridine (tBuSpy). The single crystal structures of [Cu(POP)(iPrSPy)][PF6] and [Cu(POP)(tBuSPy)][PF6] have been determined and confirm a distorted tetrahedral copper(I) centre and chelating P^P and N^S ligands in each complex. Variable temperature (VT) 1H and 31P{1H} NMR spectroscopy reveals dynamic behavior with motion of the POP backbone in [Cu(POP)(iPrSPy)][PF6] and [Cu(POP)(tBuSPy)][PF6] frozen out at 238 K. VT NMR spectroscopic data including EXSY peaks in the ROESY spectrum of [Cu(xantphos)(tBuSPy)][PF6] at 198 K reveal that two conformers exist in an approximate ratio of 5:1. Replacing bpy by the N^S ligands shifts the Cu+/Cu2+ oxidation to a higher potential. The copper(I) compounds are weak emitters in the solid state with PLQY values of <2%. These values are similar to those for [Cu(POP)(bpy)][PF6] and [Cu(xantphos)(bpy)][PF6] in the solid state.

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6

Carroll, Michael P., and Patrick J. Guiry. "P,N ligands in asymmetric catalysis." Chem. Soc. Rev. 43, no. 3 (2014): 819–33. http://dx.doi.org/10.1039/c3cs60302d.

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7

Roesky, Peter W. "P?N ligands in lanthanide chemistry." Heteroatom Chemistry 13, no. 6 (2002): 514–20. http://dx.doi.org/10.1002/hc.10096.

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8

Zhu, Ying-Gui, and Feng Gao. "catena-Poly[[diiodidomercury(II)]-μ-N,N′-p-phenylenebis(pyridine-3-carboxamide)-κ2 N:N′]." Acta Crystallographica Section E Structure Reports Online 63, no. 3 (February 16, 2007): m778—m779. http://dx.doi.org/10.1107/s160053680700709x.

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Crystals of the title compound, [HgI2(C18H14N4O2)] n , were obtained by the reaction of HgI2 and p-phenylene-bis(pyridine-3-carboxamide) in DMF. The asymmetric unit is composed of only half of the formula unit; the mercury atom lies on a crystallographic twofold rotation axis, and there is an inversion centre at the centre of the benzene ring. Each HgII atom is coordinated by two I atoms and two N atoms from two p-phenylene-bis(pyridine-3-carboxamide) (bpfb) ligands, in a distorted tetrahetral geometry. Bpfb acts as a bifunctional bridging ligand, linking HgII atoms into a one-dimensional chain. Hydrogen-bonding interactions between the O atom and the H atoms of bpfb ligands result in a two-dimensional supramolecular network.

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9

Klein, Marius, Nemrud Demirel, Alexander Schinabeck, Hartmut Yersin, and Jörg Sundermeyer. "Cu(I) Complexes of Multidentate N,C,N- and P,C,P-Carbodiphosphorane Ligands and Their Photoluminescence." Molecules 25, no. 17 (September 1, 2020): 3990. http://dx.doi.org/10.3390/molecules25173990.

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A series of dinuclear copper(I) N,C,N- and P,C,P-carbodiphosphorane (CDP) complexes using multidentate ligands CDP(Py)2 (1) and (CDP(CH2PPh2)2 (13) have been isolated and characterized. Detailed structural information was gained by single-crystal XRD analyses of nine representative examples. The common structural motive is the central double ylidic carbon atom with its characteristic two lone pairs involved in the binding of two geminal L-Cu(I) fragments at Cu–Cu distances in the range 2.55–2.67 Å. In order to enhance conformational rigidity within the characteristic Cu–C–Cu triangle, two types of chelating side arms were symmetrically attached to each phosphorus atom: two 2-pyridyl functions in ligand CDP(Py)2 (1) and its dinuclear copper complexes 2–9 and 11, as well as two diphenylphosphinomethylene functions in ligand CDP(CH2PPh2)2 (13) and its di- and mononuclear complexes 14–18. Neutral complexes were typically obtained via the reaction of 1 with Cu(I) species CuCl, CuI, and CuSPh or via the salt elimination reaction of [(CuCl)2(CDP(Py)2] (2) with sodium carbazolate. Cationic Cu(I) complexes were prepared upon treating 1 with two equivalents of [Cu(NCMe)4]PF6, followed by the addition of either two equivalents of an aryl phosphine (PPh3, P(C6H4OMe)3) or one equivalent of bisphosphine ligands bis[(2-diphenylphosphino)phenyl] ether (DPEPhos), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (XantPhos), or 1,1′-bis(diphenyl-phosphino) ferrocene (dppf). For the first time, carbodiphosphorane CDP(CH2PPh2)2 (13) could be isolated upon treating its precursor [CH(dppm)2]Cl (12) with NaNH2 in liquid NH3. A protonated and a deprotonated derivative of ligand 13 were prepared, and their coordination was compared to neutral CDP ligand 13. NMR analysis and DFT calculations reveal that the most stable tautomer of 13 does not show a CDP (or carbone) structure in its uncoordinated base form. For most of the prepared complexes, photoluminescence upon irradiation with UV light at room temperature was observed. Quantum yields (ΦPL) were determined to be 36% for dicationic [(CuPPh3)2(CDP(Py)2)](PF6)2 (4) and 60% for neutral [(CuSPh)2(CDP(CH2PPh2)2] (16).

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10

Lagaditis, Paraskevi O., Alexandre A. Mikhailine, Alan J. Lough, and Robert H. Morris. "Template Synthesis of Iron(II) Complexes Containing Tridentate P−N−S, P−N−P, P−N−N, and Tetradentate P−N−N−P Ligands." Inorganic Chemistry 49, no. 3 (February 2010): 1094–102. http://dx.doi.org/10.1021/ic901945c.

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11

Vasilenko, Vladislav, Torsten Roth, Clemens K. Blasius, Sebastian N. Intorp, Hubert Wadepohl, and Lutz H. Gade. "A modular approach to neutral P,N-ligands: synthesis and coordination chemistry." Beilstein Journal of Organic Chemistry 12 (April 29, 2016): 846–53. http://dx.doi.org/10.3762/bjoc.12.83.

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We report the modular synthesis of three different types of neutral κ2-P,N-ligands comprising an imine and a phosphine binding site. These ligands were reacted with rhodium, iridium and palladium metal precursors and the structures of the resulting complexes were elucidated by means of X-ray crystallography. We observed that subtle changes of the ligand backbone have a significant influence on the binding geometry und coordination properties of these bidentate P,N-donors.

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12

Mikhailine, Alexandre A., Eunice Kim, Carsten Dingels, Alan J. Lough, and Robert H. Morris. "Template Syntheses of Iron(II) Complexes Containing Chiral P−N−N−P and P−N−N Ligands." Inorganic Chemistry 47, no. 15 (August 2008): 6587–89. http://dx.doi.org/10.1021/ic800884c.

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13

Navarro, Miquel, Alberto Toledo, Maximilian Joost, Abderrahmane Amgoune, Sonia Mallet-Ladeira, and Didier Bourissou. "π Complexes of P^P and P^N chelated gold(i)." Chemical Communications 55, no. 55 (2019): 7974–77. http://dx.doi.org/10.1039/c9cc04266k.

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14

Mazzeo, Francesca, Fabian Brunner, Alessandro Prescimone, Edwin C. Constable, and Catherine E. Housecroft. "Intra-Cation versus Inter-Cation π-Contacts in [Cu(P^P)(N^N)][PF6] Complexes." Crystals 10, no. 1 (December 18, 2019): 1. http://dx.doi.org/10.3390/cryst10010001.

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A series of [Cu(POP)(N^N][PF6] and [Cu(xantphos)(N^N][PF6] compounds has been prepared and characterized in which POP = bis[2-(diphenylphosphanyl)phenyl]ether (IUPAC PIN oxydi(2,1-phenylene)bis(diphenylphosphane), xantphos = 4,5-bis(diphenylphosphanyl)-9,9-dimethyl-9H-xanthene (IUPAC PIN (9,9-dimethyl-9H-xanthene- 4,5-diyl)bis(diphenylphosphane)) and the N^N ligands are 4-(4-bromophenyl)-6,6′-dimethyl-2,2′- bipyridine (1), 5,5′-bis(3-methoxyphenyl)-6-methyl-2,2′-bipyridine (2), and 6-benzyl-2,2′-bipyridine (3). The single crystal structures of [Cu(xantphos)(1)][PF6]·CH2Cl2, [Cu(xantphos)(2)][PF6]·CH2Cl2 and [Cu(POP)(3)][PF6]·0.5H2O were determined by X-ray diffraction. Each complex contains a copper(I) ion in a distorted tetrahedral environment with chelating N^N and P^P ligands. In the [Cu(xantphos)(1)]+ and [Cu(xantphos)(2)]+ cations, there are face-to-face π-stackings of bpy and PPh2 phenyl rings (i.e., between the ligands); in addition in [Cu(xantphos)(2)][PF6]·CH2Cl2, inter-cation π-embraces lead to the formation of infinite chains as a primary packing motif. In [Cu(POP)(3)][PF6]·0.5H2O, centrosymmetric pairs of [Cu(POP)(3)]+ cations engage in C–H…π (phenyl to bpy) and offset face-to-face (bpy…bpy) contacts. The electrochemical and photophysical properties of the compounds containing ligands 1 and 2 are reported. They are green or yellow emitters in the solid-state (λem in the range 535–577 nm) with values for the photoluminescence quantum yield (PLQY) in the range 19%–41%.

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15

ROZANOV, I. A., D. A. MURASHOV, L. YA MEDVEDEVA, V. I. MOISEEV, and L. L. MADUSKINA. "ChemInform Abstract: New P,N-Cyclic Ligands." ChemInform 22, no. 3 (August 23, 2010): no. http://dx.doi.org/10.1002/chin.199103268.

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16

Walg, Simon P., Fabian Dietrich, Anneken Grün, Merve Cayir Kücükdisli, Yu Sun, Werner R. Thiel, and Markus Gerhards. "Synthesis and photophysical properties of multimetallic gold/zinc complexes of (P,N,N,N,P) and (P,N,N) ligands." New Journal of Chemistry 46, no. 9 (2022): 4062–71. http://dx.doi.org/10.1039/d1nj05806a.

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17

Holland, Amanda M., Allen G. Oliver, and Vlad M. Iluc. "Iron pyrrole-based PNP pincer ligand complexes as catalyst precursors." Acta Crystallographica Section C Structural Chemistry 73, no. 7 (June 28, 2017): 569–74. http://dx.doi.org/10.1107/s2053229617009287.

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The structure of a pincer ligand consists of a backbone and two `arms' which typically contain a P or N atom. They are tridentate ligands that coordinate to a metal center in a meridional configuration. A series of three iron complexes containing the pyrrole-based PNP pincer ligand 2,5-bis[(diisopropylphosphanyl)methyl]pyrrolide (PNpyrP) has been synthesized. These complexes are possible precursors to new iron catalysts. {2,5-Bis[(diisopropylphosphanyl)methyl]pyrrolido-κ3 P,N,P′}carbonylchlorido(trimethylphosphane-κP)iron(II), [Fe(C18H34NP2)Cl(C3H9P)(CO)] or [Fe(PNpyrP)Cl(PMe3)(CO)], (I), has a slightly distorted octahedral geometry, with the Cl and CO ligands occupying the apical positions. {2,5-Bis[(diisopropylphosphanyl)methyl]pyrrolido-κ3 P,N,P′}chlorido(pyridine-κN)iron(II), [Fe(C18H34NP2)Cl(C5H5N)] or [Fe(PNpyrP)Cl(py)] (py is pyridine), (II), is a five-coordinate square-pyramidal complex, with the pyridine ligand in the apical position. {2,5-Bis[(diisopropylphosphanyl)methyl]pyrrolido-κ3 P,N,P′}dicarbonylchloridoiron(II), [Fe(C18H34NP2)Cl(CO)2] or [Fe(PNpyrP)Cl(CO)2], (III), is structurally similar to (I), but with the PMe3 ligand replaced by a second carbonyl ligand from the reaction of (II) with CO. The two carbonyl ligands are in a cis configuration, and there is positional disorder of the chloride and trans carbonyl ligands.

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18

Pfaltz, A., and W. J. Drury. "Asymmetric Catalysis Special Feature Part II: Design of chiral ligands for asymmetric catalysis: From C2-symmetric P,P- and N,N-ligands to sterically and electronically nonsymmetrical P,N-ligands." Proceedings of the National Academy of Sciences 101, no. 16 (April 6, 2004): 5723–26. http://dx.doi.org/10.1073/pnas.0307152101.

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19

Zeng, Chao, Nan Wang, Tai Peng, and Suning Wang. "Copper(I) Complexes Bearing 1,2-Phenyl-Bridged P∧N, P∧N∧P, and N∧P∧N Chelate Ligands: Structures and Phosphorescence." Inorganic Chemistry 56, no. 3 (January 10, 2017): 1616–25. http://dx.doi.org/10.1021/acs.inorgchem.6b02721.

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20

Wu, Hongwei, Fang Xie, Yanlan Wang, Xiaohu Zhao, Delong Liu, and Wanbin Zhang. "Pd-catalyzed asymmetric allylic amination using easily accessible metallocenyl P,N-ligands." Organic & Biomolecular Chemistry 13, no. 14 (2015): 4248–54. http://dx.doi.org/10.1039/c5ob00032g.

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Pd-catalyzed asymmetric allylic aminations were carried out efficiently using both C₂-symmetric and non-C₂-symmetric metallocenyl P,N-ligands. A more accessible mixed ligand system of the above two was then examined, providing the amination product with high yield and excellent enantioselectivity.

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21

Shen, Lu, Yu-Yang Wang, Teng-Fei He, Lu-Yi Zou, Jing-Fu Guo, and Ai-Min Ren. "A Theoretical Investigation into the Homo- and Hetero-leptic Cu(I) Phosphorescent Complexes Bearing 2,9-dimethyl-1, 10-phenanthroline and bis [2-(diphenylphosphino)phenyl]ether Ligand." Materials 15, no. 20 (October 17, 2022): 7253. http://dx.doi.org/10.3390/ma15207253.

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Cu(I) complexes have received widespread attention as a promising alternative to traditional noble-metal complexes. Herein, we systematically study the properties of Cu(I) complexes from homo- to hetero-ligands, and found the following: (1) hetero-ligands are beneficial to regulate phosphorescent efficiency; (2) when the hetero-ligands in a tetracoordinated Cu(I) complex are 1:1, the ligands coordinate along the dx2-y2 direction of Cu(I) ion, which can observably suppress structural deformation; (3) unlike the P^P ligand, the N^N ligand can enhance the participation of Cu(I) during the transition process; (4) the addition of an appropriate amount of P^P ligand can effectively raise the energy level of HOMO (highest occupied molecular orbital), enhance the proportion of LLCT (ligand–ligand charge transfer), and thereby increase the available singlet emission transition moments which can be borrowed, thus promoting the radiative decay process. As a result, this work provides a detailed understanding of the effects of different ligands in Cu(I) complexes, and provides a valuable reference and theoretical basis for regulating and designing the phosphorescent properties of Cu(I) complexes in the future.

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22

Álvarez, Daniel, Elena López-Castro, Arturo Guerrero, Lucía Riera, Julio Pérez, Jesús Díaz, M. Isabel Menéndez, and Ramón López. "Influence of the Nucleophilic Ligand on the Reactivity of Carbonyl Rhenium(I) Complexes towards Methyl Propiolate: A Computational Chemistry Perspective." Molecules 25, no. 18 (September 10, 2020): 4134. http://dx.doi.org/10.3390/molecules25184134.

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A comparative theoretical study on the reactivity of the complexes [ReY(CO)3(bipy)] (Y = NH2, NHMe, NHpTol, OH, OMe, OPh, PH2, PHMe, PMe2, PHPh, PPh2, PMePh, SH, SMe, SPh; bipy = 2,2′-bipyridine) towards methyl propiolate was carried out to analyze the influence of both the heteroatom (N, O, P, S) and the alkyl and/or aryl substituents of the Y ligand on the nature of the product obtained. The methyl substituent tends to accelerate the reactions. However, an aromatic ring bonded to N and O makes the reaction more difficult, whereas its linkage to P and S favour it. On the whole, ligands with O and S heteroatoms seem to disfavour these processes more than ligands with N and P heteroatoms, respectively. Phosphido and thiolato ligands tend to yield a coupling product with the bipy ligand, which is not the general case for hydroxo, alcoxo or amido ligands. When the Y ligand has an O/N and an H atom the most likely product is the one containing a coupling with the carbonyl ligand, which is not always obtained when Y contains P/S. Only for OMe and OPh, the product resulting from formal insertion into the Re-Y bond is the preferred.

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23

Lenter, M., A. Levinovitz, S. Isenmann, and D. Vestweber. "Monospecific and common glycoprotein ligands for E- and P-selectin on myeloid cells." Journal of Cell Biology 125, no. 2 (April 15, 1994): 471–81. http://dx.doi.org/10.1083/jcb.125.2.471.

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E- and P-selectin are inducible cell adhesion molecules on endothelial cells, which function as Ca(2+)-dependent lectins and mediate the binding of neutrophils and monocytes. We have recently identified a 150-kD glycoprotein ligand for E-selectin on mouse myeloid cells, using a recombinant antibody-like form of mouse E-selectin. Here, we report that this ligand does not bind to an analogous P-selectin fusion protein. Instead, the chimeric P-selectin-IgG protein recognizes a 160-kD glycoprotein on the mouse neutrophil progenitor 32D cl 3, on mature mouse neutrophils and on human HL60 cells. The binding is Ca(2+)-dependent and requires the presence of sialic acid on the ligand. This P-selectin-ligand is not recognized by E-selectin. Removal of N-linked carbohydrate side chains from the 150-kD and the 160-kD monospecific selectin ligands abolishes the binding of both ligands to the respective selectin. Treatment of HL60 cells with Peptide: N-glycosidase F inhibited cell binding to P- and E-selectin. In addition, glycoproteins of 230 and 130 kD were found on mature mouse neutrophils, which bound both to E- and P-selectin in a Ca(2+)-dependent fashion. The signals detected for these ligands were 15-20-fold weaker than those for the monospecific ligands. Both proteins were heavily sialylated and selectin-binding was blocked by removal of sialic acid, but not by removal of N-linked carbohydrates. Our data reveal that E- and P-selectin recognize two categories of glycoprotein ligands: one type requires N-linked carbohydrates for binding and is monospecific for each of the two selectins and the other type binds independent of N-linked carbohydrates and is common for both endothelial selectins.

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24

Murray, Niamh S., Sarah Keller, Edwin C. Constable, Catherine E. Housecroft, Markus Neuburger, and Alessandro Prescimone. "[Cu(N^N)(P^P)]+complexes with 2,2′:6′,2′′-terpyridine ligands as the N^N domain." Dalton Transactions 44, no. 16 (2015): 7626–33. http://dx.doi.org/10.1039/c5dt00517e.

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Synthesis, structural, NMR spectroscopic and photophysical properties of the first [Cu(N^N)(POP)]⁺complexes with 2,2′:6′,2′′-terpyridines as the N^N domain are described (POP = bis(2-(diphenylphosphino)phenyl)ether).

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25

Prades, Amparo, Samuel Núñez-Pertíñez, Antoni Riera, and Xavier Verdaguer. "P-Stereogenic bisphosphines with a hydrazine backbone: from N–N atropoisomerism to double nitrogen inversion." Chemical Communications 53, no. 33 (2017): 4605–8. http://dx.doi.org/10.1039/c7cc01944k.

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26

Nishi, Tatsuya, Toshiaki Tsukuda, Michihiro Nishikawa, and Taro Tsubomura. "Crystal structure of [N,N-bis(diphenylphosphorothioyl)amidato-κ2 S,S′]bis(triphenylphosphane-κP)copper(I) dichloromethane monosolvate." Acta Crystallographica Section E Crystallographic Communications 73, no. 8 (July 4, 2017): 1105–7. http://dx.doi.org/10.1107/s2056989017009380.

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The title compound, [Cu(C24H20NP2S2)(C18H15P)2]·CH2Cl2 or [Cu(dppaS2)(PPh3)2]·CH2Cl2, is a neutral mononuclear copper(I) complex bearing an N,N-bis(diphenylphosphorothioyl)amidate (dppaS2 −) ligand and two triphenylphosphane ligands. The molecular structure shows that the two S atoms of the dppaS2 − ligand [Cu—S = 2.3462 (9) and 2.3484 (9) Å] and the two P atoms of the two triphenylphosphane ligands [Cu—P = 2.3167 (9) and 2.2969 (9) Å] coordinate to the copper(I) atom, resulting in a tetrahedral coordination geometry. The crystallographically observed molecular structure is compared to the results of DFT calculations.

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27

Ilaldinov, I. Z., D. A. Fatkulina, and R. Kadyrov. "Synthesis of camphor-based chiral P,N-ligands." Russian Journal of Organic Chemistry 47, no. 6 (June 2011): 952–53. http://dx.doi.org/10.1134/s1070428011060224.

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28

Gavrilov, Konstantin N., Alexei I. Polosukhin, Oleg G. Bondarev, Andrei V. Korostylev, Sergey E. Lyubimov, Alexei A. Shiryaev, Zoya A. Starikova, and Vadim A. Davankov. "Iminophosphites as new chiral P,N-bidentate ligands." Mendeleev Communications 11, no. 1 (January 2001): 33–35. http://dx.doi.org/10.1070/mc2001v011n01abeh001356.

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29

Loiseleur, Olivier, Masahiko Hayashi, Martine Keenan, Norbert Schmees, and Andreas Pfaltz. "Enantioselective Heck reactions using chiral P,N-ligands." Journal of Organometallic Chemistry 576, no. 1-2 (March 1999): 16–22. http://dx.doi.org/10.1016/s0022-328x(98)01049-3.

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30

Wetzel, Corinna, Peter C. Kunz, Indre Thiel, and Bernhard Spingler. "Gold(I) Catalysts with Bifunctional P, N Ligands." Inorganic Chemistry 50, no. 16 (August 15, 2011): 7863–70. http://dx.doi.org/10.1021/ic2011259.

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31

Perera, SD. "(Arene)Ru(II) Complexes of P-N Ligands." OUSL Journal 4 (December 1, 2007): 72. http://dx.doi.org/10.4038/ouslj.v4i0.339.

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32

Carroll, Michael P., and Patrick J. Guiry. "ChemInform Abstract: P,N Ligands in Asymmetric Catalysis." ChemInform 45, no. 17 (April 10, 2014): no. http://dx.doi.org/10.1002/chin.201417268.

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33

Zhou, Yong Gui, and Xue Long Hou. "ChemInform Abstract: 1,2-P,N-Bidentate Ferrocenyl Ligands." ChemInform 42, no. 26 (June 3, 2011): no. http://dx.doi.org/10.1002/chin.201126221.

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34

Bowen, Richard J., Manuel A. Fernandes, Patricia W. Gitari, Marcus Layh, and Richard M. Moutloali. "Synthesis and Reactions of Mixed N,P Ligands." European Journal of Inorganic Chemistry 2005, no. 10 (May 2005): 1955–63. http://dx.doi.org/10.1002/ejic.200400607.

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35

Crawford, Sarah M., Craig A. Wheaton, Vinayak Mishra, and Mark Stradiotto. "Probing the effect of donor-fragment substitution in Mor-DalPhos on palladium-catalyzed C–N and C–C cross-coupling reactivity." Canadian Journal of Chemistry 96, no. 6 (June 2018): 578–86. http://dx.doi.org/10.1139/cjc-2017-0749.

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The competitive catalytic screening of 18 known and newly prepared Mor-DalPhos ligand variants in the palladium-catalyzed cross-coupling of chlorobenzene with aniline, octylamine, morpholine, indole, ammonia, or acetone is presented, including ligands derived from the new secondary phosphine HP(Me2Ad)2 (Me2Ad = 3,5-dimethyladamantyl). Although triarylphosphine ancillary ligand variants performed poorly in these test reactions, ligands featuring either PAd2 or P(Me2Ad)2 donors (Ad = 1-adamantyl) gave rise to superior catalytic performance. Multiple Mor-DalPhos variants proved effective in cross-couplings involving aniline, octylamine, or morpholine; conversely, only a smaller subset of ligands proved useful in related cross-couplings of indole, ammonia, or acetone. In the case of the N-arylation of indole, a Mor-DalPhos ligand variant featuring ortho-disposed PAd2 and dimethylmorpholino donor fragments (L13) proved superior to all other ligands surveyed, including the parent ligand Mor-DalPhos (L5). Conversely, L5 was found to be superior to all other ligands in the palladium-catalyzed monoarylation of ammonia. Ligand L6 (i.e., the P(Me2Ad)2 variant of L5) proved superior to all other ligands in the monoarylation of acetone and, with the exception of indole N-arylation, was the most broadly useful of the Mor-DalPhos ligands surveyed herein.

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36

Nohara, Isaak, Aramis Keller, Nikolai Tarassenko, Alessandro Prescimone, Edwin C. Constable, and Catherine E. Housecroft. "Heteroleptic [Cu(P^P)(N^N)][PF6] Compounds with Isomeric Dibromo-1,10-Phenanthroline Ligands." Inorganics 8, no. 1 (January 10, 2020): 4. http://dx.doi.org/10.3390/inorganics8010004.

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A series of [Cu(P^P)(N^N)][PF6] compounds are reported in which N^N is 2,9-dibromo-1,10-phenanthroline (2,9-Br2phen), 3,8-dibromo-1,10-phenanthroline (3,8-Br2phen) or 4,7-dibromo-1,10-phenanthroline (4,7-Br2phen) and P^P is bis(2-(diphenylphosphano)phenyl)ether (POP) or 4,5-bis(diphenylphosphano)-9,9-dimethylxanthene (xantphos). The compounds were characterized by solution multinuclear NMR spectroscopy, mass spectrometry and a single-crystal X-ray analysis. Each compound underwent a partially reversible or irreversible copper-centred oxidation, the highest potential being for 2,9-Br2phen-containing compounds. In solution, the compounds are weak yellow or orange emitters, whereas powdered samples exhibit yellow emissions with photoluminescence quantum yields of up to 45% for [Cu(xantphos)(2,9-Br2phen)][PF6] with an excited state lifetime τ1/2 = 9.9 μs. Values of λemmax for [Cu(POP)(2,9-Br2phen)][PF6] and [Cu(xantphos)(2,9-Br2phen)][PF6] are blue-shifted with respect to compounds with the 3,8-and 4,7-isomers, both in solution and in the solid state.

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37

Kühl, Olaf. "The natural bite angle — Seen from a ligand's point of view." Canadian Journal of Chemistry 85, no. 3 (March 1, 2007): 230–38. http://dx.doi.org/10.1139/v07-023.

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The natural bite angle concept is examined using N,N′-bisphosphino urea ligands as rigid scaffolds. The ligand has an upper limit of about 95° for the observed bite angle in chelate complexes, but prefers a much lower one. The ligand can be described as possessing downward flexibility. The dependence of the bite angle on the P—P distance within the ligand and the M—P bond length is illustrated. The metal tries to force the ligand into its own preferred structure, whereas the ligand wants to achieve a short P—P distance. A truly rigid ligand such as the N,N′-bisphosphino urea family is thus seen to clearly discriminate between metal atoms according to their individual assertiveness, using the P—P distance in the complex as a measure. Although the natural bite angle concept is valid and helpful in determining the possible bite-angle range for ligands before it is actually synthesised, its practical applicability seems to be limited to those cases where the flexibility range of the ligand allows for only one metal-preferred bite angle to be realized.Key words: natural bite angle, ligand effects, ligand design.

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38

Orgué, Sílvia, Areli Flores-Gaspar, Maria Biosca, Oscar Pàmies, Montserrat Diéguez, Antoni Riera, and Xavier Verdaguer. "Stereospecific SN2@P reactions: novel access to bulky P-stereogenic ligands." Chemical Communications 51, no. 99 (2015): 17548–51. http://dx.doi.org/10.1039/c5cc07504a.

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Hydrolysis of bulky aminophosphine boranes followed by nucleophilic substitution of the resulting phosphinous acid boranes provides a novel access to P*-ligands. Using this methodology, a P*,N ligand was synthesized and applied to the asymmetric Ir-catalyzed hydrogenation.

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39

Müller, Gabi, Martti Klinga, Peter Osswald, Markku Leskelä, and Bernhard Rieger. "Palladium Complexes with Bidentate P,N Ligands: Synthesis, Characterization and Application in Ethene Oligomerization." Zeitschrift für Naturforschung B 57, no. 7 (July 1, 2002): 803–9. http://dx.doi.org/10.1515/znb-2002-0713.

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Palladium complexes of two different P,N ligands (a phosphane-pyridine and a phosphane-imine ligand) were synthesized and characterized. Single crystal X-ray structure analyses of the palladium diiodide compounds revealed a square-planar coordination geometry at the metal center with a longer Pd-I bond in trans-position to the phosphorus atom. The chloro-methyl palladium species of the phosphane-pyridine ligand was applied for the oligomerization of ethene using a borate salt as cocatalyst.

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40

Jansen, Achim, and Stephan Pitter. "Synthesis of Hemilabile P,N Ligands: ω-2-Pyridyl-n-alkylphosphines." Monatshefte für Chemie / Chemical Monthly 130, no. 6 (June 1999): 783–94. http://dx.doi.org/10.1007/pl00010260.

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41

Qin, Hao, Chuanjin Hou, Dinghua Liang, Xinwei He, Ling Li, and Xiangping Hu. "Chiral P,N,N-Ligands for Pd-Catalyzed Asymmetric Allylic Substitutions." Chinese Journal of Organic Chemistry 44, no. 1 (2024): 282. http://dx.doi.org/10.6023/cjoc202306004.

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42

Ben-Daat, Hagit, Gabriel B. Hall, Thomas L. Groy, and Ryan J. Trovitch. "Rational Design of Rhodium Complexes Featuring κ4-N,N,N,N- and κ5-N,N,N,P,P-Bis(imino)pyridine Ligands." European Journal of Inorganic Chemistry 2013, no. 25 (July 4, 2013): 4430–42. http://dx.doi.org/10.1002/ejic.201300263.

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43

Karasik, Andrey A., Elvira I. Musina, Anna S. Balueva, and Oleg G. Sinyashin. "Novel Biomimetic Cyclic P,N-Ligands. Lability of P-CH2-N Fragment: Problem or Advantage?" Phosphorus, Sulfur, and Silicon and the Related Elements 188, no. 1-3 (January 1, 2013): 27–28. http://dx.doi.org/10.1080/10426507.2012.741156.

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44

Keller, Antoni, Beata Jasionka, Tadeusz Głowiak, Aleksei Ershov, and Renata Matusiak. "Cyclic oxycarbene and vinylidene complexes of ruthenium with (PP) and (NN) type ligands." Inorganica Chimica Acta 344 (February 2003): 49–60. http://dx.doi.org/10.1016/s0020-1693(02)01313-0.

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45

Lv, Ming. "catena-Poly[[[aquazinc(II)]-bis[μ-(p-phenylenedioxy)diacetato]-zinc(II)-μ-1,4-bis(1H-imidazol-l-yl)butane] dihydrate]." Acta Crystallographica Section E Structure Reports Online 63, no. 11 (October 26, 2007): m2833. http://dx.doi.org/10.1107/s1600536807052518.

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In the title compound, {[Zn2(C10H8O6)2(C10H14N4)(H2O)2]·2H2O} n , the ZnII atom is six-coordinated by one N atom from one 1,4-bis(1H-imidazol-l-yl)butane ligand and five O atoms from two different (p-phenylenedioxy)diacetate ligands and one water molecule in a very distorted ZnNO5 octahedral environment. Two (p-phenylenedioxy)diacetate ligands bridge two ZnII atoms to form a dimer. The dimers are further linked by the centrosymmetric 1,4-bis(1H-imidazol-l-yl)butane ligands, thus forming a chain structure. O—H...O hydrogen bonds link the chains, forming a three-dimensional supramolecular network.

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46

Hameury, S., C. Gourlaouen, and M. Sommer. "Balancing steric and electronic effects of bidentate, mixed P,N ligands to control Kumada catalyst transfer polycondensation of a sterically hindered thiophene." Polymer Chemistry 9, no. 24 (2018): 3398–405. http://dx.doi.org/10.1039/c8py00452h.

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47

Monkowius, Uwe, Manfred Zabel, Michel Fleck, and Hartmut Yersin. "Gold(I) Complexes Bearing P∩N-Ligands: An Unprecedented Twelve-membered Ring Structure Stabilized by Aurophilic Interactions." Zeitschrift für Naturforschung B 64, no. 11-12 (December 1, 2009): 1513–24. http://dx.doi.org/10.1515/znb-2009-11-1235.

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The P∩N-ligands Ph2Pqn, 1, Ph2 Piqn, 2, Ph2 Ppym, 3, and the As∩N-ligands Ph2Asqn, 4, Ph2Asiqn, 5, (Ph = phenyl, qn = 8-quinoline, iqn = 1-isoquinoline, pym = 2-pyrimidine) have been synthesized, the ligands 2 and 5 for the first time. Their ligand properties were probed by the synthesis of gold(I) complexes. Reaction with (tht)AuCl (tht = tetrahydrothiophene) yielded the chlorogold complexes Ph2RP-Au-Cl (R = qn, 6; iqn, 7; pym, 8) and Ph2RAs-Au-Cl (R = qn, 9; iqn, 10) in high yields. Further treatment of 7 and 8 with one equivalent of AgBF4 provided the complexes [(Ph2Piqn)Au]BF4, 11, [(Ph2Ppym)Au]BF4, 12, and [(Ph2Piqn)Au(tht)]BF4, 14. For comparison, the previously reported complex [(Ph2Ppy)Au]BF4 (py = pyridine), 13, was re-investigated. The compounds were characterized by elemental analyses, mass spectrometry and NMR spectroscopy. In addition, the solid-state structures of 2, 3, 6, 7, 9 - 14 have been determined by X-ray crystallography. The chloro-gold compounds crystallize in the common rod-like structure known from R3EAuCl (R = aryl, E = P, As) complexes without further aggregation via aurophilic interactions. In all cases the phosphine acts as a monodentate ligand. In the solid state compounds 11 - 13 feature an unprecedented cyclic trinuclear aggregation pattern, in which the Au(I) atoms are linearly coordinated by the bridging phosphine ligands forming a cyclic (P-Au-N)3 arrangement. The resulting twelvemembered ring is further stabilized by Au · · · Au interactions. Due to the presence of these Au · · · Au contacts, 11 - 13 are emissive in the solid state but not in solution

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48

Brunner, Fabian, Laura Martínez-Sarti, Sarah Keller, Antonio Pertegás, Alessandro Prescimone, Edwin C. Constable, Henk J. Bolink, and Catherine E. Housecroft. "Peripheral halo-functionalization in [Cu(N^N)(P^P)]+ emitters: influence on the performances of light-emitting electrochemical cells." Dalton Transactions 45, no. 38 (2016): 15180–92. http://dx.doi.org/10.1039/c6dt02665f.

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Trends in the performance data of [Cu(N^N)(P^P)]⁺-based LECs in which N^N ligands bear peripheral F, Cl, Br or I substituents reveal that fluoro-groups are beneficial, but heavier halo-substituents lead to poor devices.

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49

Dahiya, Gaurav, Mukesh Pappoppula, and Aaron Aponick. "Configuration Sampling With Five‐Membered Atropisomeric P , N ‐Ligands." Angewandte Chemie International Edition 60, no. 36 (August 3, 2021): 19604–8. http://dx.doi.org/10.1002/anie.202102642.

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50

Dahiya, Gaurav, Mukesh Pappoppula, and Aaron Aponick. "Configuration Sampling With Five‐Membered Atropisomeric P , N ‐Ligands." Angewandte Chemie 133, no. 36 (August 3, 2021): 19756–60. http://dx.doi.org/10.1002/ange.202102642.

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