0000000000727368
AUTHOR
Jas S. Ward
Selective Formation of S4- and T-Symmetric Supramolecular Tetrahedral Cages and Helicates in Polar Media Assembled via Cooperative Action of Coordination and Hydrogen Bonds
We report on the synthesis and self-assembly study of novel supramolecular monomers encompassing quadruple hydrogen-bonding motifs and metal-coordinating 2,2'-bipyridine units. When mixed with metal ions such as Fe2+ or Zn2+, the tetrahedron cage complexes are formed in quantitative yields and full diastereoselectivity, even in highly polar acetonitrile or methanol solvents. The symmetry of the complexes obtained has been shown to depend critically on the flexibility of the ligand. Restriction of the rotation of the hydrogen-bonding unit with respect to the metal-coordinating site results in a T-symmetric cage, whereas introducing flexibility either through a methylene linker or rotating be…
Modified ent-Abietane Diterpenoids from the Leaves of Suregada zanzibariensis
The leaf extract of Suregada zanzibariensis gave two new modified ent-abietane diterpenoids, zanzibariolides A (1) and B (2), and two known triterpenoids, simiarenol (3) and β-amyrin (4). The structures of the isolated compounds were elucidated based on NMR and MS data analysis. Single-crystal X-ray diffraction was used to establish the absolute configurations of compounds 1 and 2. The crude leaf extract inhibited the infectivity of herpes simplex virus 2 (HSV-2, IC50 11.5 μg/mL) and showed toxicity on African green monkey kidney (GMK AH1) cells at CC50 52 μg/mL. The isolated compounds 1–3 showed no anti-HSV-2 activity and exhibited insignificant toxicity against GMK AH1 cells at ≥100 μM. p…
Heterometallic Au(I)–Cu(I) Clusters : Luminescence Studies and 1O2 Production
Two different organometallic gold(I) compounds containing naphthalene and phenanthrene as fluorophores and 2-pyridyldiphenylphosphane as the ancillary ligand were synthesized (compounds 1 with naphthalene and 2 with phenanthrene). They were reacted with three different copper(I) salts with different counterions (PF6–, OTf–, and BF4–; OTf = triflate) to obtain six Au(I)/Cu(I) heterometallic clusters (compounds 1a–c for naphthalene derivatives and 2a–c for phenanthrene derivatives). The heterometallic compounds present red pure room-temperature phosphorescence in both solution, the solid state, and air-equilibrated samples, as a difference with the dual emission recorded for the gold(I) precu…
Halogen-Bonded [N–I–N]− Complexes with Symmetric or Asymmetric Three-Center–Four-Electron Bonds
A series of LH[Z–I–Z] halogen(I) complexes, where Z = saccharinato or phthalimido anions and LH = pyridinium, pyrazinium, tetrabutyl (TBA)- or tetramethylammonium (TMA) cations, were prepared, structurally characterized, and discussed as complexes consisting of a [N–I–N]− anion with a three-center–four-electron (3c-4e) halogen bond, and a hydrogen-bonding (pyridinium or pyrazinium) or inert (TBA or TMA) cation. The symmetric [N–I–N]− anion, reminiscent of the triiodide [I–I–I]− anion, is found to be structurally equivalent to its cationic analogue [N–I–N]+ with N–I bond lengths of 2.26 Å. In contrast to the homoleptic [N–I–N]+ complexes, asymmetry of the N–I bond lengths (2.21 and 2.28 Å) w…
Helicates with Ether-Substituted Catechol Esters as Ligands
European journal of organic chemistry 2020(32), 5161-5172 (2020). doi:10.1002/ejoc.202000843
Nucleophilic iodonium interactions (NIIs) in 2-coordinate iodine(i) and silver(i) complexes
The generality of nucleophilic iodonium interactions (NIIs) has been demonstrated by preparing a range of silver(i) and iodonium (I+) complexes and studying their 15N NMR chemical shifts, with the first example of a NII-complex involving a 2-coordinate silver(i) complex being confirmed by X-ray crystallography, and its nucleophilicity studied by DFT calculations.
Effect of Gold(I) on the Room-Temperature Phosphorescence of Ethynylphenanthrene.
The synthesis of two series of gold(I) complexes containing the general formulae PR 3 ‐Au‐C≡C‐phenanthrene (PR 3 = PPh 3 ( 1a / 2a ), PMe 3 ( 1b / 2b ), PNaph 3 ( 1c / 2c )) or (diphos)(Au‐C≡C‐phenanthrene) 2 (diphos = 1,1‐ bis (diphenylphosphino)methane, dppm ( 1d / 2d ); 1,4‐ bis (diphenylphosphino)butane, dppb ( 1e / 2e )) have been synthesized. The two series differ on the position of the alkynyl substituent on the phenanthrene chromophore, being at the 9‐position (9‐ethynylphenanthrene) for the L1 ‐series and at the 2‐position (2‐ethynylphenanthrene) for the L2 ‐series. The compounds have been fully characterized by 1 H and 31 P NMR and IR spectroscopy, mass spectrometry and single cry…
Protonation-induced fluorescence modulation of carbazole-based emitters
The development of purely organic fluorescence emitters is of great importance for their low cost and high performance. Responding to this demand, carbazole is a promising emitter due to its extensive freedom for functionalisation, high thermal and chemical stability, as well as low cost. Herein, the effect of protonation on the fluorescence of various pyridine-functionalised carbazole-based bipolar host materials was studied both in solution and in the solid-state. The restriction of intramolecular rotation of the molecules upon protonation of the pyridyl-moiety together with easier planarization of the protonated acceptor and the donor moieties and relocalisation of the LUMO orbital on th…
Iodination of antipyrine with [N–I–N]+ and carbonyl hypoiodite iodine(i) complexes
A series of iodine(I) complexes, both known and new, were synthesised and the dependence of iodination reactivity on the identity of the Lewis bases and anions present was investigated. Using a previously established screening protocol based on the iodination of antipyrine to iodo-antipyrine, the capability of the iodine(I) species to perform the iodination was tested and compared, especially in relation to Barluenga's reagent, [I(pyridine)2]BF4. The results indicated that the identity of both the Lewis bases and the anion influence the iodination capability of the iodine(I) species, and that the less efficient reagents can deliver favourably comparable percentage conversions with longer re…
Toward Near-Infrared Emission in Pt(II)-Cyclometallated Compounds: From Excimers’ Formation to Aggregation-Induced Emission
Two series of Pt(II)-cyclometallated compounds containing N^C^N tridentate and alkynyl-chromophore ligands have been synthesized and structurally characterized. The N^C^N ligands differ on the presence of R1 = H or F in the central aromatic ring, while six different chromophores have been introduced to the alkynyl moiety. Single-crystal X-ray structures for some of the compounds reveal the presence of weak intermolecular contacts responsible for the formation of some dimers or aggregates. The photophysical characterization shows the presence of two emission bands in solution assigned to the 3π–π* transition from the N^C^N ligands mixed with 3MLCT/3ILCT transitions (higher energy band) in de…
Crotofolane Diterpenoids and Other Constituents Isolated from Croton kilwae
Six new crotofolane diterpenoids (1-6) and 13 known compounds (7-19) were isolated from the MeOH- CH2Cl2 (1:1, v/v) extracts of the leaves and stem bark of Croton kilwae. The structures of the new compounds were elucidated by extensive analysis of spectroscopic and mass spectrometric data. The structure of crotokilwaepoxide A (1) was confirmed by single -crystal X-ray diffraction, allowing for the determination of its absolute configuration. The crude extracts and the isolated compounds were investigated for antiviral activity against respiratory syncytial virus (RSV) and human rhinovirus type-2 (HRV-2) in HEp-2 and HeLa cells, respectively, for antibacterial activity against the Gram-posit…
Ligand exchange among iodine(I) complexes
A detailed investigation of ligand exchange between iodine(I) ions in [N⋯I⋯N]+ halogen-bonded complexes is presented. Ligand exchange reactions were conducted to successfully confirm whether iodine(I) complex formation, via the classical [N⋯Ag⋯N]+ to [N⋯I⋯N]+ cation exchange reaction from their analogous Ag+ complexes, could be determined solely by using 1H NMR spectroscopy. In instances where the formation of the iodine(I) complex was unclear or in low yield by the traditional cation exchange reaction, a ligand exchange reaction was used to form the desired iodine(I) complexes in a quantitative manner. Mixing two homoleptic [N⋯I⋯N]+ iodine(I) complexes in 1 : 1 ratio was found to undergo a…
Asymmetric [N–I–N]+ halonium complexes
The first asymmetric halogen-bonded iodonium complexes [I(py)(4-DMAP)]PF6 (2c) and [I(py)(4-Etpy)]PF6 (2e) were prepared via [N–Ag–N]+ → [N–I–N]+ cation exchange of their analogous 2-coordinate silver complexes. The complexes were characterised by 1H and 1H–15N HMBC NMR spectroscopy, and single crystal X-ray crystallography.
Synthesis of Polycyclic Indolines by Utilizing a Reduction/Cyclization Cascade Reaction
European journal of organic chemistry 2021(45), 6097-6101 (2021). doi:10.1002/ejoc.202101191
Room-Temperature Phosphorescence and Efficient Singlet Oxygen Production by Cyclometalated Pt(II) Complexes with Aromatic Alkynyl Ligands
The synthesis of five novel cyclometalated platinum(II) compounds containing five different alkynyl-chromophores was achieved by the reaction of the previously synthesized Pt–Cl cyclometalated compound (1) with the corresponding RC≡CH by a Sonogashira reaction. It was observed that the spectral and photophysical characteristics of the cyclometalated platinum(II) complexes (Pt–Ar) are essentially associated with the platinum-cyclometalated unit. Room-temperature emission of the Pt–Ar complexes was attributed to phosphorescence in agreement with DFT calculations. Broad nanosecond (ns)-transient absorption spectra were observed with decays approximately identical to those obtained from the emi…
Selective Synthesis of Z -Silyl Enol Ethers via Ni-Catalyzed Remote Functionalization of Ketones
Journal of the American Chemical Society : JACS 143(22), 8375-8380 (2021). doi:10.1021/jacs.1c01797
Solid‐state NMR Spectroscopy of Iodine(I) Complexes
Solid-state NMR has been applied to a series of Barluenga-type iodine(I) [L-I-L]PF6 (L=pyridine, 4-ethylpyridine, 4-dimethylaminopyridine, isoquinoline) complexes as their hexafluorophosphate salts, as well as their respective non-liquid ligands (L), their precursor silver(I) complexes, and the respective N-methylated pyridinium and quinolinium hexafluorophoshate salts. These results are compared and contrasted to the corresponding solution studies and single-crystal X-ray structures. As the first study of its kind on the solid-state NMR behavior of halogen(I) complexes, practical considerations are also discussed to encourage wider utilization of this technique in the future. peerReviewed
A supramolecular system that strictly follows the binding mechanism of conformational selection
Induced fit and conformational selection are two dominant binding mechanisms in biology. Although induced fit has been widely accepted by supramolecular chemists, conformational selection is rarely studied with synthetic systems. In the present research, we report a macrocyclic host whose binding mechanism is unambiguously assigned to conformational selection. The kinetic and thermodynamic aspects of this system are studied in great detail. It reveals that the kinetic equation commonly used for conformational selection is strictly followed here. In addition, two mathematical models are developed to determine the association constants of the same guest to the two host conformations. A “confo…
Self-assembly of M4L4 tetrahedral cages incorporating pendant P=S and P=Se functionalised ligands
Herein, the synthesis of metal–organic tetrahedral cages featuring flexible thio- and selenophosphate-based ligands is described. The cages were prepared by sub-component self-assembly of A=P(OC6H4NH2-4)3 (A = S, Se) or S=P(SC6H4NH2-4)3,2-pyridinecarboxaldehyde, and either Fe[BF4]2 or Co[BF4]2. Preliminary host–guest studies into the ability of the pendant PQS and PQSe groups to interact with suitable substrates will be discussed. peerReviewed
Shedding Light on the Interactions of Hydrocarbon Ester Substituents upon Formation of Dimeric Titanium(IV) Triscatecholates in DMSO Solution
Abstract The dissociation of hierarchically formed dimeric triple lithium bridged triscatecholate titanium(IV) helicates with hydrocarbyl esters as side groups is systematically investigated in DMSO. Primary alkyl, alkenyl, alkynyl as well as benzyl esters are studied in order to minimize steric effects close to the helicate core. The 1H NMR dimerization constants for the monomer–dimer equilibrium show some solvent dependent influence of the side chains on the dimer stability. In the dimer, the ability of the hydrocarbyl ester groups to aggregate minimizes their contacts with the solvent molecules. Due to this, most solvophobic alkyl groups show the highest dimerization tendency followed by…
Carbonyl hypoiodites from pivalic and trimesic acid and their silver(I) intermediates
The first tris(O–I–N) carbonyl hypoiodites have been synthesised based on trimesic acid and pyridine or 4-methylpyridine, with their structures definitively confirmed by single crystal X-ray diffraction (SCXRD). The more soluble carbonyl hypoiodites based on pivalic acid have also been studied via NMR, SCXRD, and computational analyses, enabling the study of the direct silver(I) precursor and intermediates of the resulting carbonyl hypoiodites generated using a range of substituted pyridines. peerReviewed
Self-assembly of M4L4tetrahedral cages incorporating pendant PS and PSe functionalised ligands
Herein, the synthesis of metal–organic tetrahedral cages featuring flexible thio- and selenophosphate-based ligands is described. The cages were prepared by sub-component self-assembly of AP(OC6H4NH2-4)3 (A = S, Se) or SP(SC6H4NH2-4)3, 2-pyridinecarboxaldehyde, and either Fe[BF4]2 or Co[BF4]2. Preliminary host–guest studies into the ability of the pendant PS and PSe groups to interact with suitable substrates will be discussed.
A “nucleophilic” iodine in a halogen-bonded iodonium complex manifests an unprecedented I+···Ag+ interaction
Summary When an electron is removed from a halogen atom, it forms a halenium ion X+ (X = I, Br, Cl). In halogen bonding (XB), X+ is considered as a strong XB donor, and when interacting with two XB acceptors (e.g., pyridine), it forms a halonium XB complex with a [N–I–N] three-center-four-electron bond with the two XB acceptors. An unprecedented I+···Ag+ interaction occurs between a [L1–I–L1]+ halogen-bonded complex and a [L2–Ag–L2]+ complex in which the iodonium ion acts like a nucleophile and donates electrons to the silver(I) cation. The X-ray diffraction analysis reveals a short contact [3.4608(3) A] between the I+ and Ag+ cations, and ITC measurements give a ΔG of −6.321 kcal/mol and K…
Intra- vs Intermolecular Aurophilic Contacts in Dinuclear Gold(I) Compounds: Impact on the Population of the Triplet Excited State.
Two series of dinuclear gold(I) complexes that contain two Au–chromophore units (chromophore = dibenzofurane or dimethylfluorene) connected through a diphosphane bridge that differs in the flexibility and length (diphosphane = dppb for 1,4-bis(diphenylphosphino)butane, DPEphos for bis[(2-diphenylphosphino)phenyl]ether, xanthphos for 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene, and BiPheP for 2,2′-bis(diphenylphosphino)-1,1′-biphenyl) have been synthesized and structurally characterized. Their photophysical properties have been carefully investigated, paying attention to the role of the presence, or absence, of aurophilic contacts and their nature (intra- or intermolecular character). Th…
Iron(III) Chloride as a Mild Catalyst for the Dearomatizing Cyclization of N-Acylindoles
A catalytic approach for the preparation of indolines by dearomatizing cyclization is presented. FeCl3 acts as a catalyst to afford tetracyclic 5a,6-dihydro-12H-indolo[2,1-b][1,3]benzoxazin-12-ones in good yields. The cyclization also proceeds with tosylamides forming C-N bonds in 53% yield.
The solid-state hierarchy and iodination potential of [bis(3-acetaminopyridine)iodine(I)]PF6
The first iodine(I) complex bearing hydrogen-bond donor and acceptor groups, [bis(3-acetaminopyridine)iodine(I)]PF6 (3), was synthesised, which exhibited two temperature-dependent solid-state connectivities of the hydrogen bonding. Upon reaction of 3 with tBuOMe, unprecedented iodination of a tBu methyl group proceeded under exceptionally mild conditions in good yield. peerReviewed
Aggregation versus Biological Activity in Gold(I) Complexes. An Unexplored Concept
The aggregation process of a series of mono- and dinuclear gold(I) complexes containing a 4-ethynylaniline ligand and a phosphane at the second coordination position (PR3-Au-C≡CC6H4-NH2, complexes 1-5, and (diphos)(Au-C≡CC6H4-NH2)2, complexes 6-8), whose biological activity was previously studied by us, has been carefully analyzed through absorption, emission, and NMR spectroscopy, together with dynamic light scattering and small-angle X-ray scattering. These experiments allow us to retrieve information about how the compounds enter the cells. It was observed that all compounds present aggregation in fresh solutions, before biological treatment, and thus they must be entering the cells as a…
Expansion and Compression of a Helicate with Central Diol-Units as Stereocontrolling Moieties
The dicatechol ester ligand 2-H4 forms the compressed helicate Li4[(2)3Ti2] which upon removal of the internally bound lithium cations expands. In the compressed form, the chiral diol units control the stereochemistry of the complex which is lost upon expansion of the system. peerReviewed
Carbonyl Hypoiodites as Extremely Strong Halogen Bond Donors
Abstract Neutral halogen‐bonded O−I−N complexes were prepared from in situ formed carbonyl hypoiodites and aromatic organic bases. The carbonyl hypoiodites have a strongly polarized iodine atom with larger σ‐holes than any known uncharged halogen bond donor. Modulating the Lewis basicity of the selected pyridine derivatives and carboxylates leads to halogen‐bonded complexes where the classical O−I⋅⋅⋅N halogen bond transforms more into a halogen‐bonded COO−⋅⋅⋅I−N+ ion‐pair (salt) with an asymmetric O−I−N moiety. X‐ray analyses, NMR studies, and calculations reveal the halogen bonding geometries of the carbonyl hypoiodite‐based O−I−N complexes, confirming that in the solid‐state the iodine at…
Dimeric iodine(i) and silver(i) cages from tripodal N-donor ligands via the [N–Ag–N]+ to [N–I–N]+ cation exchange reaction
The directionality of the [N–I–N]+ halogen bond makes iodine(I) ions impeccable tools in the design and construction of [N–I–N]+ halogen-bonded assemblies. The synthesis of dimeric iodine(I) cages with imidazole-derived N-donor tripodal ligands is described, as well as their corresponding silver(I) precursors. The addition of elemental iodine to the parent two-coordinate Ag(I) complexes produces iodine(I) complexes with three-center four-electron (3c–4e) [N–I–N]+ bonds. Complex formation via this cation exchange was confirmed by 1H and 1H–15N HMBC NMR studies in solution, and additionally by electrospray ionisation and ion mobility mass spectrometry analysis (MS) in the gas phase. The struc…
Fluorescence enhancement of quinolines by protonation.
A study of the fluorescence enhancement of isoquinoline, acridine (benzo[b]quinoline) and benzo[h]quinoline is reported with six organic acids of different pKa values. Protonation was found to be an effective tool in the fluorescence enhancement of quinolines. A significant increase in the fluorescence intensity is observed only when strong acids are used, resulting in an over 50-fold increase in fluorescence with trifluoroacetic or benzenesulfonic acid and isoquinoline in a 1.5 : 1 ratio. The benzenesulfonic acid was found to be the most effective in the protonation of the bases despite its higher pKa value compared to trifluoro- and trichloroacetic acid. The X-ray crystal structures of 14…
Iodine(i) complexes incorporating sterically bulky 2-substituted pyridines
The silver(I) and iodine(I) complexes of the 2-substituted pyridines 2-(diphenylmethyl)pyridine (1) and 2-(1,1-diphenylethyl)pyridine (2), along with their potential protonated side products, were synthesised to investigate the steric limitations of iodine(I) complex formation. The complexes were characterised by 1H and 1H–15N HMBC NMR, X-ray crystallography, and DFT calculations. The solid-state structures for the silver(I) and iodine(I) complexes were extensively compared to the literature and analysed by DFT to examine the influence of the sterically bulky pyridines and their anions. peerReviewed
A 2,3-dialkoxynaphthalene-based naphthocage
A 2,3-dialkoxynaphthalene-based naphthocage has been synthesized. This naphthocage prefers to bind small organic cations with its low-symmetry conformation, which is in contrast to 2,6-dialkoxynaphthalene-based naphthocages. Self-sorting of these two naphthocages with two structurally similar guests tetramethylammonium and tetraethylammonium was achieved as well. peerReviewed
Luminescent Pt-II and Pt-IV Platinacycles with Anticancer Activity Against Multiplatinum-Resistant Metastatic CRC and CRPC Cell Models
Platinum-based chemotherapy persists to be the only effective therapeutic option against a wide variety of tumours. Nevertheless, the acquisition of platinum resistance is utterly common, ultimately cornering conventional platinum drugs to only palliative in many patients. Thus, encountering alternatives that are both effective and non-cross-resistant is urgent. In this work, we report the synthesis, reduction studies, and luminescent properties of a series of cyclometallated (C,N,N')PtIV compounds derived from amine- imine ligands, and their remarkable efficacy at the high nanomolar range and complete lack of cross57 resistance, as an intrinsic property of the platinacycle, against multipl…
Cyclic Sulfoximine and Sulfonimidamide Derivatives by Copper‐Catalyzed Cross‐Coupling Reactions with Elemental Sulfur
Copper-catalyzed cross-coupling reactions of α-bromoaryl NH-sulfoximines with elemental sulfur lead to benzo[d][1,3,2]dithiazole-1-oxides, which represent a new class of three-dimensional heterocycles. The reactions proceed under mild conditions showing good functional group and heterocycle tolerance. By imination/oxidation, the initial cross-coupling products can be converted to unprecedented cyclic sulfonimidamides derivatives. Furthermore, a seven-membered heterocycle was obtained by a ruthenium-catalyzed ring-expansion with ethyl propiolate. peerReviewed
Synthesis of N‐Fused Indolines via Copper (II)‐Catalyzed Dearomatizing Cyclization of Indoles
Advanced synthesis & catalysis 363(12), 3121-3126 (2021). doi:10.1002/adsc.202100290
Synthesis of N‐Monosubstituted Sulfondiimines by Metal‐free Iminations of Sulfiliminium Salts
Sulfondiimines are marginalized entities among nitrogencontaining organosulfur compounds, despite offering promising properties for applications in various fields including medicinal and agrochemical. Herein, we present a metal-free and rapid synthetic procedure for the synthesis of N-monosubstituted sulfondiimines that overcomes current limitations in their synthetic accessibility. Particularly, S,S-dialkyl substrates, which are commonly difficult to convert by existing methods, react well with a combination of iodine, 1,8-diazabicyclo[5.4.0]undec-7-en (DBU), and iminoiodanes (PhINR) in acetonitrile (MeCN) to furnish the corresponding sulfondiimines in yields up to 85% (25 examples). Valua…
Cover Feature: Synthesis of Polycyclic Indolines by Utilizing a Reduction/Cyclization Cascade Reaction (Eur. J. Org. Chem. 45/2021)
Chiral carbonyl hypoiodites
Three chiral carbonyl hypoiodites, R–C(O)OI, have been prepared from N-protected (S)-valine to give the ligand-stabilised (S)-valinoyl hypoiodite complexes with 4-dimethylaminopyridine, 4-pyrrolidinopyridine, and 4-morpholinopyridine as the stabilising ligands. The identity of the complexes was established by NMR (1H, 13C, 1H–15N HMBC) and single crystal X-ray diffraction analysis. peerReviewed
Luminescent PtII and PtIV Platinacycles with Anticancer Activity Against Multiplatinum‐Resistant Metastatic CRC and CRPC Cell Models
Abstract: Platinum‐based chemotherapy persists to be the only effective therapeutic option against a wide variety of tumours. Nevertheless, the acquisition of platinum resistance is utterly common, ultimately cornering conventional platinum drugs to only palliative in many patients. Thus, encountering alternatives that are both effective and non‐cross‐resistant is urgent. In this work, we report the synthesis, reduction studies and luminescent properties of a series of cyclometallated (C,N,N’) PtIV compounds derived from amine‐imine ligands, and their remarkable efficacy at the high nanomolar range and complete lack of cross‐resistance, as an intrinsic property of the platinacycle, against …
Iodine(I) and Silver(I) Complexes Incorporating 3-Substituted Pyridines
Building upon the first report of a 3-acetaminopyridine-based iodine(I) complex (1b) and its unexpected reactivity toward tBuOMe, several new 3-substituted iodine(I) complexes (2b–5b) have been synthesized. The iodine(I) complexes were synthesized from their analogous silver(I) complexes (2a–5a) via a silver(I) to iodine(I) cation exchange reaction, incorporating functionally related substituents as 3-acetaminopyridine in 1b; 3-acetylpyridine (3-Acpy; 2), 3-aminopyridine (3-NH2py; 3), and 3-dimethylaminopyridine (3-NMe2py; 4), as well as the strongly electron-withdrawing 3-cyanopyridine (3-CNpy; 5), to probe the possible limitations of iodine(I) complex formation. The individual properties …
Asymmetric [N–I–N]+ halonium complexes
The first asymmetric halogen-bonded iodonium complexes [I(py)(4-DMAP)]PF6 (2c) and [I(py)(4-Etpy)]PF6 (2e) were prepared via [N-Ag-N]+ → [N-I-N]+ cation exchange of their analogous 2-coordinate silver complexes. The complexes were characterised by 1H and 1H-15N HMBC NMR spectroscopy, and single crystal X-ray crystallography. peerReviewed
CCDC 2080290: Experimental Crystal Structure Determination
Related Article: Essi Taipale, Nikita A. Durandin, Jagadish K. Salunke, Nuno R. Candeias, Tero-Petri Ruoko, Jas S. Ward, Arri Priimagi, Kari Rissanen|2022|Mat.Advs.|3|1703|doi:10.1039/D1MA00438G
CCDC 2080285: Experimental Crystal Structure Determination
Related Article: Essi Taipale, Nikita A. Durandin, Jagadish K. Salunke, Nuno R. Candeias, Tero-Petri Ruoko, Jas S. Ward, Arri Priimagi, Kari Rissanen|2022|Mat.Advs.|3|1703|doi:10.1039/D1MA00438G
CCDC 2070639: Experimental Crystal Structure Determination
Related Article: Andrea Pinto, Catarina Roma-Rodrigues, Jas S. Ward, Rakesh Puttreddy, Kari Rissanen, Pedro V. Baptista, Alexandra R. Fernandes, Joa��o Carlos Limag, Laura Rodri��guez|2021|Inorg.Chem.|60|18753|doi:10.1021/acs.inorgchem.1c02359
CCDC 1950786: Experimental Crystal Structure Determination
Related Article: A. Carel N. Kwamen, Marcel Schlottmann, David Van Craen, Elisabeth Isaak, Julia Baums, Li Shen, Ali Massomi, Christoph Räuber, Benjamin P. Joseph, Gerhard Raabe, Christian Göb, Iris M. Oppel, Rakesh Puttreddy, Jas S. Ward, Kari Rissanen, Roland Fröhlich, Markus Albrecht|2020|Chem.-Eur.J.|26|1396|doi:10.1002/chem.201904639
CCDC 2193612: Experimental Crystal Structure Determination
Related Article: Araceli de Aquino, Jas S. Ward, Kari Rissanen, Gabriel Aullón, João Carlos Lima, Laura Rodríguez|2022|Inorg.Chem.|61|20931|doi:10.1021/acs.inorgchem.2c03351
CCDC 1977489: Experimental Crystal Structure Determination
Related Article: Jingyu Zhang, Jing Li, Jas S. Ward, Khai-Nghi Truong, Kari Rissanen, Markus Albrecht|2020|J.Org.Chem.|85|12160|doi:10.1021/acs.joc.0c01373
CCDC 2000976: Experimental Crystal Structure Determination
Related Article: Essi Tervola, Khai-Nghi Truong, Jas S. Ward, Arri Priimagi, Kari Rissanen|2020|RSC Advances|10|29385|doi:10.1039/D0RA04691D
CCDC 1885471: Experimental Crystal Structure Determination
Related Article: Patrick W. V. Butler, Jas S. Ward|2019|Z.Anorg.Allg.Chem.|645|694|doi:10.1002/zaac.201900063
CCDC 2068113: Experimental Crystal Structure Determination
Related Article: Shilin Yu, Jas S. Ward, Khai-Nghi Truong, Kari Rissanen|2021|Angew.Chem.,Int.Ed.|60|20739|doi:10.1002/anie.202108126
CCDC 1951280: Experimental Crystal Structure Determination
Related Article: Qixun Shi, Xiaohong Zhou, Wei Yuan, Xiaoshi Su, Algirdas Neniškis, Xin Wei, Lukas Taujenis, Gustautas Snarskis, Jas S. Ward, Kari Rissanen, Javier de Mendoza, Edvinas Orentas|2020|J.Am.Chem.Soc.|142|3658|doi:10.1021/jacs.0c00722
CCDC 2105110: Experimental Crystal Structure Determination
Related Article: Eric Kramer, Shilin Yu, Jas S. Ward, Kari Rissanen|2021|Dalton Trans.|50|14990|doi:10.1039/D1DT03324G
CCDC 2000985: Experimental Crystal Structure Determination
Related Article: Essi Tervola, Khai-Nghi Truong, Jas S. Ward, Arri Priimagi, Kari Rissanen|2020|RSC Advances|10|29385|doi:10.1039/D0RA04691D
CCDC 2225069: Experimental Crystal Structure Determination
Related Article: Milla Mattila, Kari Rissanen, Jas S. Ward|2023|Chem.Commun.|59|4648|doi:10.1039/D3CC00259D
CCDC 1885470: Experimental Crystal Structure Determination
Related Article: Patrick W. V. Butler, Jas S. Ward|2019|Z.Anorg.Allg.Chem.|645|694|doi:10.1002/zaac.201900063
CCDC 2080284: Experimental Crystal Structure Determination
Related Article: Essi Taipale, Nikita A. Durandin, Jagadish K. Salunke, Nuno R. Candeias, Tero-Petri Ruoko, Jas S. Ward, Arri Priimagi, Kari Rissanen|2022|Mat.Advs.|3|1703|doi:10.1039/D1MA00438G
CCDC 2242257: Experimental Crystal Structure Determination
Related Article: Marco T. Passia, Niklas Bormann, Jas S. Ward, Kari Rissanen, Carsten Bolm|2023|Angew.Chem.,Int.Ed.|62||doi:10.1002/anie.202305703
CCDC 2067949: Experimental Crystal Structure Determination
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CCDC 2245212: Experimental Crystal Structure Determination
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CCDC 2080288: Experimental Crystal Structure Determination
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CCDC 1919187: Experimental Crystal Structure Determination
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CCDC 2064893: Experimental Crystal Structure Determination
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CCDC 1996938: Experimental Crystal Structure Determination
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CCDC 2193619: Experimental Crystal Structure Determination
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CCDC 2225023: Experimental Crystal Structure Determination
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CCDC 2192598: Experimental Crystal Structure Determination
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CCDC 2009560: Experimental Crystal Structure Determination
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CCDC 1917460: Experimental Crystal Structure Determination
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CCDC 2068107: Experimental Crystal Structure Determination
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CCDC 2009558: Experimental Crystal Structure Determination
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CCDC 1977492: Experimental Crystal Structure Determination
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CCDC 2000981: Experimental Crystal Structure Determination
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CCDC 1977495: Experimental Crystal Structure Determination
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CCDC 2000978: Experimental Crystal Structure Determination
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CCDC 2064892: Experimental Crystal Structure Determination
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CCDC 1977494: Experimental Crystal Structure Determination
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CCDC 2067947: Experimental Crystal Structure Determination
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CCDC 2000982: Experimental Crystal Structure Determination
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CCDC 2192597: Experimental Crystal Structure Determination
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CCDC 2080292: Experimental Crystal Structure Determination
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CCDC 1970146: Experimental Crystal Structure Determination
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CCDC 2080291: Experimental Crystal Structure Determination
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CCDC 2000986: Experimental Crystal Structure Determination
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CCDC 2080283: Experimental Crystal Structure Determination
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CCDC 2193615: Experimental Crystal Structure Determination
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CCDC 2080293: Experimental Crystal Structure Determination
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CCDC 2105108: Experimental Crystal Structure Determination
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CCDC 2225071: Experimental Crystal Structure Determination
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CCDC 2242258: Experimental Crystal Structure Determination
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CCDC 1957891: Experimental Crystal Structure Determination
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CCDC 2062095: Experimental Crystal Structure Determination
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CCDC 2067946: Experimental Crystal Structure Determination
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CCDC 2000983: Experimental Crystal Structure Determination
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CCDC 1977488: Experimental Crystal Structure Determination
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CCDC 1938076: Experimental Crystal Structure Determination
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CCDC 1958053: Experimental Crystal Structure Determination
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CCDC 2067943: Experimental Crystal Structure Determination
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CCDC 1958051: Experimental Crystal Structure Determination
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CCDC 2062096: Experimental Crystal Structure Determination
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CCDC 2019550: Experimental Crystal Structure Determination
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CCDC 2178008: Experimental Crystal Structure Determination
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CCDC 2067948: Experimental Crystal Structure Determination
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CCDC 2105109: Experimental Crystal Structure Determination
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CCDC 1885473: Experimental Crystal Structure Determination
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CCDC 2080286: Experimental Crystal Structure Determination
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CCDC 1977487: Experimental Crystal Structure Determination
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CCDC 2064897: Experimental Crystal Structure Determination
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CCDC 2084411: Experimental Crystal Structure Determination
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CCDC 2193617: Experimental Crystal Structure Determination
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CCDC 2003776: Experimental Crystal Structure Determination
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CCDC 2068111: Experimental Crystal Structure Determination
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CCDC 2062097: Experimental Crystal Structure Determination
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CCDC 2019549: Experimental Crystal Structure Determination
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CCDC 1996937: Experimental Crystal Structure Determination
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CCDC 2000980: Experimental Crystal Structure Determination
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CCDC 2070637: Experimental Crystal Structure Determination
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CCDC 1885481: Experimental Crystal Structure Determination
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CCDC 2064896: Experimental Crystal Structure Determination
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CCDC 2062098: Experimental Crystal Structure Determination
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CCDC 2009557: Experimental Crystal Structure Determination
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CCDC 1938073: Experimental Crystal Structure Determination
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CCDC 2068110: Experimental Crystal Structure Determination
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CCDC 1885472: Experimental Crystal Structure Determination
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CCDC 1950443: Experimental Crystal Structure Determination
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CCDC 2079433: Experimental Crystal Structure Determination
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CCDC 1938074: Experimental Crystal Structure Determination
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CCDC 1970147: Experimental Crystal Structure Determination
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CCDC 1938075: Experimental Crystal Structure Determination
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CCDC 2064898: Experimental Crystal Structure Determination
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CCDC 1958052: Experimental Crystal Structure Determination
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CCDC 2062101: Experimental Crystal Structure Determination
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CCDC 2000977: Experimental Crystal Structure Determination
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CCDC 2064895: Experimental Crystal Structure Determination
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CCDC 2079434: Experimental Crystal Structure Determination
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CCDC 2000979: Experimental Crystal Structure Determination
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CCDC 1996939: Experimental Crystal Structure Determination
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CCDC 1977491: Experimental Crystal Structure Determination
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CCDC 2080687: Experimental Crystal Structure Determination
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CCDC 1977486: Experimental Crystal Structure Determination
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CCDC 2070640: Experimental Crystal Structure Determination
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CCDC 2067945: Experimental Crystal Structure Determination
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CCDC 2000984: Experimental Crystal Structure Determination
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CCDC 2193613: Experimental Crystal Structure Determination
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CCDC 1996942: Experimental Crystal Structure Determination
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CCDC 1919188: Experimental Crystal Structure Determination
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CCDC 2080287: Experimental Crystal Structure Determination
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CCDC 2080689: Experimental Crystal Structure Determination
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CCDC 1996944: Experimental Crystal Structure Determination
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CCDC 1996940: Experimental Crystal Structure Determination
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CCDC 2009559: Experimental Crystal Structure Determination
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CCDC 2067944: Experimental Crystal Structure Determination
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CCDC 1996943: Experimental Crystal Structure Determination
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CCDC 2193614: Experimental Crystal Structure Determination
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CCDC 1919186: Experimental Crystal Structure Determination
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CCDC 2079430: Experimental Crystal Structure Determination
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CCDC 2019551: Experimental Crystal Structure Determination
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CCDC 2000989: Experimental Crystal Structure Determination
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CCDC 2079432: Experimental Crystal Structure Determination
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CCDC 2080289: Experimental Crystal Structure Determination
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