Chiral bisoxazoline ligands designed to stabilize bimetallic complexes

• Deepankar Das,
• Rudrajit Mal,
• Nisha Mittal,
• Zhengbo Zhu,
• Thomas J. Emge and
• Daniel Seidel

Beilstein J. Org. Chem. 2018, 14, 2002–2011, doi:10.3762/bjoc.14.175

• deprotonation, 32-H2 provides a dianionic ligand with three donor nitrogen atoms per metal center. Ligand 32-H2 forms complexes with different nickel, copper, zinc and palladium salts. Shown in Figure 6 is the molecular structure of 32·Zn2Cl2. Each unit of the complex 32·Zn2Cl2 consists of two zinc(ΙΙ) centers

• the development of new catalytic enantioselective transformations. Examples of chiral bimetallic complexes utilized in asymmetric catalysis. Previously reported bisoxazoline ligands capable of stabilizing bimetallic complexes. Thermal ellipsoid plot (50% probability) of the molecular structure of 16

• with a = 14.1829(5) Å, b = 14.8645(6) Å, c = 25.2342(10) Å, α = 90°, β = 90°, γ = 90°, V = 5319.9(4) Å3, Z = 4, Dc = 1.450 mg m−3 and μ(Mo Kα) = 1.017 mm−1. Thermal ellipsoid plot (50% probability) of the molecular structure of 25·Ni2(OAc). Hydrogen and solvate atoms have been omitted for clarity: (A

Synthesis of new p-tert-butylcalix[4]arene-based polyammonium triazolyl amphiphiles and their binding with nucleoside phosphates

• Vladimir A. Burilov,
• Guzaliya A. Fatikhova,
• Mariya N. Dokuchaeva,
• Ramil I. Nugmanov,
• Diana A. Mironova,
• Pavel V. Dorovatovskii,
• Victor N. Khrustalev,
• Svetlana E. Solovieva and
• Igor S. Antipin

Beilstein J. Org. Chem. 2018, 14, 1980–1993, doi:10.3762/bjoc.14.173

• [63] was used. Then optimized structures were calculated using DFT calculations with CPCM model of solvation in water with Gaussian 09 program [47] with B3LYP functional on 6-311g basis level. Molecular structure of 8a (50% ellipsoids). The dashed line indicates the alternative position of the

A hemicryptophane with a triple-stranded helical structure

• Augustin Long,
• Olivier Perraud,
• Erwann Jeanneau,
• Christophe Aronica,
• Jean-Pierre Dutasta and
• Alexandre Martinez

Beilstein J. Org. Chem. 2018, 14, 1885–1889, doi:10.3762/bjoc.14.162

• / UCBL, Université Claude Bernard Lyon 1, 6 rue victor Grignard, 69622 Villeurbanne cedex, France 10.3762/bjoc.14.162 Abstract A hemicryptophane cage bearing amine and amide functions in its three linkers was synthesized in five steps. The X-ray molecular structure of the cage shows a triple-stranded

• (400 MHz, CDCl3). X-ray molecular structure of 1. Hydrogen atoms are omitted for clarity; dashed lines represent hydrogen bonds. (a) Structure of compound 6. (b) 1H NMR of 6 (CDCl3, 400 MHz). (c) 1H NMR of 1 (CDCl3, 400 MHz). Synthesis of 1. Supporting Information Supporting Information File 396

Water-soluble SNS cationic palladium(II) complexes and their Suzuki–Miyaura cross-coupling reactions in aqueous medium

• Alphonse Fiebor,
• Richard Tia,
• Banothile C. E. Makhubela and
• Henok H. Kinfe

Beilstein J. Org. Chem. 2018, 14, 1859–1870, doi:10.3762/bjoc.14.160

• -donating substituents, in the coupling reaction. Examples of reported SCS palladium(II) pincer complexes 1–13. a) Reported SNS palladium(II) pincer complexes 14–16 as catalysts for Suzuki–Miyaura cross coupling [34]; b) Proposed SNS palladium(II) pincer complexes 17. Molecular structure of 17d. Selected

First thia-Diels–Alder reactions of thiochalcones with 1,4-quinones

• Grzegorz Mlostoń,
• Katarzyna Urbaniak,
• Paweł Urbaniak,
• Anna Marko,
• Anthony Linden and
• Heinz Heimgartner

Beilstein J. Org. Chem. 2018, 14, 1834–1839, doi:10.3762/bjoc.14.156

• (for C26H20O2S): 395 (100, [M − 1]−). ORTEP plot [29] of the molecular structure of 4k showing the major conformation of the disordered thiophene ring (50% probability ellipsoids; arbitrary numbering of the atoms). Products of the reactions of thiochalcones 1a and 1b with 1,4-benzoquinone (2a) and of

Recent advances in phosphorescent platinum complexes for organic light-emitting diodes

• Cristina Cebrián and
• Matteo Mauro

Beilstein J. Org. Chem. 2018, 14, 1459–1481, doi:10.3762/bjoc.14.124

• OLEDs. In fact, Wang and collaborators reported a red-emitting device based on Pt(fppz)2 [39], where fppz is 3-(trifluoromethyl)-5-(2-pyridyl)-1H-pyrazolate, that attained remarkable EQE of 31% [40] (see Figure 7 for the chemical structure of the complex). With the aim of correlating molecular structure

A three-armed cryptand with triazine and pyridine units: synthesis, structure and complexation with polycyclic aromatic compounds

• Claudia Lar,
• Adrian Woiczechowski-Pop,
• Attila Bende,
• Ioana Georgeta Grosu,
• Natalia Miklášová,
• Elena Bogdan,
• Niculina Daniela Hădade,
• Anamaria Terec and
• Ion Grosu

Beilstein J. Org. Chem. 2018, 14, 1370–1377, doi:10.3762/bjoc.14.115

• 21.34 M−1 ± 2.7909, respectively (M−1 = L/mol). The details of these experiments are given in Supporting Information File 1. The first step in the molecular modelling investigations was the optimization of the equilibrium geometry of the molecular structure of cryptand 2, the result being shown in

One hundred years of benzotropone chemistry

• Arif Dastan,
• Haydar Kilic and
• Nurullah Saracoglu

Beilstein J. Org. Chem. 2018, 14, 1120–1180, doi:10.3762/bjoc.14.98

• molecular structure of 4,5-benzotropone (11) was determined by Hata’s group [50]. X-ray diffraction analysis showed that the molecule is approximately planar and the bond alternation in the seven-membered ring and C=O bond length support satisfactory aromaticity. 2.1. Synthesis of 4,5-benzotropone (11

Fluorocyclisation via I(I)/I(III) catalysis: a concise route to fluorinated oxazolines

• Felix Scheidt,
• Christian Thiehoff,
• Gülay Yilmaz,
• Stephanie Meyer,
• Constantin G. Daniliuc,
• Gerald Kehr and
• Ryan Gilmour

Beilstein J. Org. Chem. 2018, 14, 1021–1027, doi:10.3762/bjoc.14.88

• the structure of oxazoline 2c bearing a p-NO2 group (Figure 4 and Table 2) [39]. The molecular structure reveals the expected gauche arrangement with a dihedral angle FCCO ≈ −73.4° due to σC–C→σC–F* and σC–H→σC–O* interactions. This observation is in agreement with the fluorine gauche effect

• increased to 32 hours. Yields refer to isolated values whilst NMR yields are given in parentheses (19F NMR using ethyl fluoroacetate as an internal standard). X-ray molecular structure of compound 2c. Thermal ellipsoids shown at the 50% propability level. Torsion angle (F1–C10–C9–O1 −73.4°) consistent with

Diastereoselective auxiliary- and catalyst-controlled intramolecular aza-Michael reaction for the elaboration of enantioenriched 3-substituted isoindolinones. Application to the synthesis of a new pazinaclone analogue

• Romain Sallio,
• Stéphane Lebrun,
• Frédéric Capet,
• Francine Agbossou-Niedercorn,
• Christophe Michon and
• Eric Deniau

Beilstein J. Org. Chem. 2018, 14, 593–602, doi:10.3762/bjoc.14.46

• -transfer catalyst; 3-substituted isoindolinones; Introduction Isoindolinones I (Figure 1), e.g., 2,3-dihydro-1H-isoindol-1-ones, also called phthalimidines are bicyclic lactams whose molecular structure is the basis of a wide range of alkaloids and biologically active compounds [1][2][3][4][5][6][7][8][9

Recent advances on organic blue thermally activated delayed fluorescence (TADF) emitters for organic light-emitting diodes (OLEDs)

• Thanh-Tuân Bui,
• Fabrice Goubard,
• Malika Ibrahim-Ouali,
• Didier Gigmes and
• Frédéric Dumur

Beilstein J. Org. Chem. 2018, 14, 282–308, doi:10.3762/bjoc.14.18

• diphenylsulfone or benzophenone as the acceptors. Here again, the higher twisted molecular structure of T4 was beneficial in terms of ΔEST, color purity and EL performances. Thus, the higher internal torsion of T4 furnished OLEDs with a deeper blue emission (0.154, 0.107) than devices fabricated with T3 (0.174

Aminosugar-based immunomodulator lipid A: synthetic approaches

• Alla Zamyatina

Beilstein J. Org. Chem. 2018, 14, 25–53, doi:10.3762/bjoc.14.3

Regioselective decarboxylative addition of malonic acid and its mono(thio)esters to 4-trifluoromethylpyrimidin-2(1H)-ones

• Sergii V. Melnykov,
• Andrii S. Pataman,
• Yurii V. Dmytriv,
• Svitlana V. Shishkina,
• Mykhailo V. Vovk and
• Volodymyr A. Sukach

Beilstein J. Org. Chem. 2017, 13, 2617–2625, doi:10.3762/bjoc.13.259

• -isomers. N1(3)-Unsubstituted products 4j, 5n,o, 6n,o, and 9–11d, unavailable by direct decarboxylative addition, are readily accessible by TFA-mediated cleavage of the corresponding N1(3)-PMB substituted precursors. Summary of the present study. Molecular structure of compound 11b. Two enantiomers form a

Pyrene–nucleobase conjugates: synthesis, oligonucleotide binding and confocal bioimaging studies

• Artur Jabłoński,
• Yannic Fritz,
• Hans-Achim Wagenknecht,
• Rafał Czerwieniec,
• Tytus Bernaś,
• Damian Trzybiński,
• Krzysztof Woźniak and
• Konrad Kowalski

Beilstein J. Org. Chem. 2017, 13, 2521–2534, doi:10.3762/bjoc.13.249

• proceeded smoothly to yield 5 as colorless solid in 85% yield (Scheme 1). All pyrenyl derivatives 1–5 were characterized by 1H NMR, 13C NMR, and IR spectroscopy, mass spectrometry and elemental analysis, and the analytical data confirmed the proposed structures. Furthermore the molecular structure of

Syntheses, structures, and stabilities of aliphatic and aromatic fluorous iodine(I) and iodine(III) compounds: the role of iodine Lewis basicity

• Tathagata Mukherjee,
• Soumik Biswas,
• Andreas Ehnbom,
• Subrata K. Ghosh,
• Ibrahim El-Zoghbi,
• Nattamai Bhuvanesh,
• Hassan S. Bazzi and
• John A. Gladysz

Beilstein J. Org. Chem. 2017, 13, 2486–2501, doi:10.3762/bjoc.13.246

• structure determined, as summarized in Table 1 and the experimental section. Two views of the molecular structure and key metrical parameters are provided in Figure 2. Two perspectives of the unit cell (Z = 8) are provided in Figure 3. There are some unusual features associated with the packing and space

• para and ortho to the iodine atoms are denoted ° and ◊ (red = ArI; blue = ArICl2). Two views of the molecular structure of 1,3,5-(Rf6)2C6H3I with thermal ellipsoids at the 50% probability level. Key bond lengths (Å) and angles (°): C1–I1 2.099(3), C1–C2 1.391(4), C2–C3 1.386(4), C3–C4 1.393(4), C4–C5

• the solvents, starting materials, and instrumentation employed, and additional spectroscopic, structural, and computational data, including a molecular structure file that can be read by the program Mercury [75] and contains the optimized geometries of all computed structures [76]. Supporting

Synthesis of naturally-derived macromolecules through simplified electrochemically mediated ATRP

• Paweł Chmielarz,
• Tomasz Pacześniak,
• Katarzyna Rydel-Ciszek,
• Izabela Zaborniak,
• Paulina Biedka and
• Andrzej Sobkowiak

Beilstein J. Org. Chem. 2017, 13, 2466–2472, doi:10.3762/bjoc.13.243

• efficient polymerization [56]. Therefore, seATRP offers a new opportunity to synthesize well-defined star-like polymers with predefined molecular structure. The main objective of this study is to present the first example of a synthesis of a macromolecule initiator from the group of flavonoids and with well

Solvent-free copper-catalyzed click chemistry for the synthesis of N-heterocyclic hybrids based on quinoline and 1,2,3-triazole

• Martina Tireli,
• Silvija Maračić,
• Stipe Lukin,
• Marina Juribašić Kulcsár,
• Dijana Žilić,
• Mario Cetina,
• Ivan Halasz,
• Silvana Raić-Malić and
• Krunoslav Užarević

Beilstein J. Org. Chem. 2017, 13, 2352–2363, doi:10.3762/bjoc.13.232

• the reaction was not complete. ESR spectra of samples obtained after milling by methods 2a (black), 2b (red) and 2c (blue). The inset shows the spectrum of [Cu(OAc)2(H2O)]2 [53]. All spectra are recorded at room temperature. X-ray structure of the triazole compounds. (a) Molecular structure of 5, with

Synthesis and photophysical properties of novel benzophospholo[3,2-b]indole derivatives

• Mio Matsumura,
• Mizuki Yamada,
• Atsuya Muranaka,
• Misae Kanai,
• Naoki Kakusawa,
• Daisuke Hashizume,
• Masanobu Uchiyama and
• Shuji Yasuike

Beilstein J. Org. Chem. 2017, 13, 2304–2309, doi:10.3762/bjoc.13.226

• tetracyclic moieties are planar. The benzophosphole-fused indoles, such as phosphine oxide, phospholium salt, and borane complex, exhibited strong photoluminescence in dichloromethane (Φ = 67–75%). Keywords: benzophospholo[3,2-b]indole; DFT calculation; molecular structure; phosphole derivatives

• -fused benzoheteroles containing the group 15 and 16 elements using the ring-closing reaction of dilithium compounds with electrophiles bearing heteroatoms [36]. In continuation of our research, we were interested in the synthesis, molecular structure, and physicochemical properties of the parent

Synthesis and application of trifluoroethoxy-substituted phthalocyanines and subphthalocyanines

• Satoru Mori and
• Norio Shibata

Beilstein J. Org. Chem. 2017, 13, 2273–2296, doi:10.3762/bjoc.13.224

• 14 exhibited aggregation behavior by an intramolecular stacking interaction between the units (Figure 5). On the other hand, the trifluoroethoxy-substituted trimer 13 did not exhibit such aggregation behavior and adopted a “windmill-like molecular structure” by the repulsive action of the

• spectra of 9 (A) and 5 (B). Structure of binuclear phthalocyanines linked by a triazole linker. Structure of trinuclear phthalocyanines linked by a triazole linker, and windmill-like molecular structure vs aggregated structure. Direction of energy transfer of phthalocyanine–fullerene conjugates. Structure

Structural diversity in the host–guest complexes of the antifolate pemetrexed with native cyclodextrins: gas phase, solution and solid state studies

• Magdalena Ceborska,
• Magdalena Zimnicka,
• Aneta Aniela Kowalska,
• Kajetan Dąbrowa and
• Barbara Repeć

Beilstein J. Org. Chem. 2017, 13, 2252–2263, doi:10.3762/bjoc.13.222

• still presents a challenge for medicinal and pharmaceutical studies, involving the search for new molecules acting as folate inhibitors [11][12], as well as their recognition mechanisms [13][14]. The molecular structure of PTX closely resembles folic acid (FA, Figure 1a), and hence, it belongs to the

The effect of milling frequency on a mechanochemical organic reaction monitored by in situ Raman spectroscopy

• Patrick A. Julien,
• Ivani Malvestiti and
• Tomislav Friščić

Beilstein J. Org. Chem. 2017, 13, 2160–2168, doi:10.3762/bjoc.13.216

• molecular structure rather than its crystallinity, offering a powerful tool for in situ studies of mechanochemical organic reactions that often proceed through amorphous or eutectic intermediates. We now report a Raman spectroscopy study of the effect of ball milling frequency on the course of a model

Mechanochemical synthesis of thioureas, ureas and guanidines

• Vjekoslav Štrukil

Beilstein J. Org. Chem. 2017, 13, 1828–1849, doi:10.3762/bjoc.13.178

• -thiourea 21a with 4-chloro- and 4-nitrophenyl isothiocyanates. This study demonstrated that solid-state ball milling can efficiently be employed for desymmetrization of ortho- and para-phenylenediamines, enabling selective functionalization of small symmetrical molecules through the extension of molecular

• structure in a one-pot two-step mechanochemical sequence. Another typical synthetic method for the preparation of thioureas, particularly if the desired isothiocyanate is not available, is the condensation of an amine with carbon disulfide [36]. This reaction proceeds through the formation of a

Theoretical simulation of the infrared signature of mechanically stressed polymer solids

• Matthew S. Sammon,
• Milan Ončák and
• Martin K. Beyer

Beilstein J. Org. Chem. 2017, 13, 1710–1716, doi:10.3762/bjoc.13.165

• in stress-induced aging of polymeric materials [1][10]. On the other hand, elegant routes have been established to harness this effect for the design of self-healing and stress-responsive materials [11][12][13][14][15]. The influence of an external force on the molecular structure of a polymer can be

Grip on complexity in chemical reaction networks

• Albert S. Y. Wong and
• Wilhelm T. S. Huck

Beilstein J. Org. Chem. 2017, 13, 1486–1497, doi:10.3762/bjoc.13.147

• true when those changes induce systems beyond a critical value, where the resulting abrupt shifts or phase transitions become unpredictable [20][21][22]. The analysis of the structure and the dynamics of a complex web of intricate interactions is a risk in removing the link between molecular structure

• borrowing principles from chemical engineering [37]. Isolating the influence of molecular structure on network function and dynamics will reveal the rules governing CRNs, as well as the complexity in systems like the cell. Minimal chemical reaction networks Network motifs assembled from feedback loops Much

• oscillation periods enable the construction of more complex systems capable of dynamical self-assembly. In this case, it is a dynamic self-assembly that is exactly out-of-phase with the initial oscillations. Correlating the molecular structure to network behavior This design strategy enables the chemist to

Nitration of 5,11-dihydroindolo[3,2-b]carbazoles and synthetic applications of their nitro-substituted derivatives

• Roman A. Irgashev,
• Nikita A. Kazin,
• Gennady L. Rusinov and
• Valery N. Charushin

Beilstein J. Org. Chem. 2017, 13, 1396–1406, doi:10.3762/bjoc.13.136

• desired product in 88% yield. At the same time, in the experiment with fuming nitric acid (5 equiv), used instead of acetyl nitrate (Table 1, entry 5), we have obtained a mixture of compound 2a and byproducts again. The molecular structure of compound 2a has been proved unequivocally by X-ray