Coordination-driven self-assembly of discrete Ru₆–Pt₆ prismatic cages

• Aderonke Ajibola Adeyemo and
• Partha Sarathi Mukherjee

Beilstein J. Org. Chem. 2018, 14, 2242–2249, doi:10.3762/bjoc.14.199

• All efforts to obtain single crystals of the prismatic cages were unsuccessful so far. Thus the structures of 3a and 3b were optimized to get insights into their structural features. The tritopic platinum(II) metalloligand was optimized using the B3LYP method while the heterometallic cage structures

Evaluation of dispersion type metal···π arene interaction in arylbismuth compounds – an experimental and theoretical study

• Ana-Maria Preda,
• Małgorzata Krasowska,
• Lydia Wrobel,
• Philipp Kitschke,
• Phil C. Andrews,
• Jonathan G. MacLellan,
• Lutz Mertens,
• Marcus Korb,
• Tobias Rüffer,
• Heinrich Lang,
• Alexander A. Auer and
• Michael Mehring

Beilstein J. Org. Chem. 2018, 14, 2125–2145, doi:10.3762/bjoc.14.187

• ][47]. A more convenient synthetic route makes use of the Grignard reagent phenylmagnesium bromide and its reaction with bismuth trichloride [48]. Following this approach with slight modifications provides Ph3Bi with a yield of more than 80%. Crystallization from EtOH gave single crystals of the

• (C6H3-t-Bu2-3,5)2BiCl (5) Colorless single crystals suitable for X-ray crystallography were isolated upon crystallization from a CH2Cl2 solution at ambient temperature (for 4) and at −28 °C (for 5). Compounds 4 and 5·2CH2Cl2 crystallize in the hexagonal space group P63 and orthorhombic space group Pna21

• isolated another polymorph 1b by crystallization from the melt. Polymorph 1b was obtained starting from 1a in a temperature-dependent PXRD experiment (see Supporting Information File 1, Figure S1). The polymorph 1b was obtained as a microcrystalline material, but Andrews and MacLellan did obtain single

Coordination-driven self-assembly vs dynamic covalent chemistry: versatile methods for the synthesis of molecular metallarectangles

• Li-Li Ma,
• Jia-Qin Han,
• Wei-Guo Jia and
• Ying-Feng Han

Beilstein J. Org. Chem. 2018, 14, 2027–2034, doi:10.3762/bjoc.14.178

• ). Notably, the isolated yields of the metallarectangles are higher than the overall yields of the two-step method. Since attempts to obtain X-ray quality single crystals of the target metallarectangles were unsuccessful, molecular simulations were performed to gain further insight into the structures of the

Synthesis and characterization of π–extended “earring” subporphyrins

• Haiyan Guan,
• Mingbo Zhou,
• Bangshao Yin,
• Ling Xu and
• Jianxin Song

Beilstein J. Org. Chem. 2018, 14, 1956–1960, doi:10.3762/bjoc.14.170

• significantly from the saddle-shaped or nearly planar porphyrin core. To elucidate the differences in their structures, we endeavored to cultivate single crystals of 3 and collected the data. The diffraction data unambiguously confirmed the designated structure (Figure 2) and revealed that all peripheral C–C

• the metal does not change the antiaromatic pathways in 3. Fortunately we obtained single crystals of 3Pd from its CH2Cl2/CDCl3/MeOH solution via vapor diffusion. All of the bond lengths were carefully measured based on the diffraction results (Figure 4). We found that despite all peripheral C–C bond

Synthesis of 9-arylalkynyl- and 9-aryl-substituted benzo[b]quinolizinium derivatives by Palladium-mediated cross-coupling reactions

• Siva Sankar Murthy Bandaru,
• Darinka Dzubiel,
• Heiko Ihmels,
• Mohebodin Karbasiyoun,
• Mohamed M. A. Mahmoud and
• Carola Schulzke

Beilstein J. Org. Chem. 2018, 14, 1871–1884, doi:10.3762/bjoc.14.161

• , so that the pure products were only available by crystallization from appropriate solvents, which resulted in lower yields of these products. Single crystal X-ray diffraction analysis of 9-(arylethynyl)benzo[b]quinolizinium derivatives 2a and 2b Single crystals of derivatives 2a and 2b were obtained

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

• representative X-ray crystal structure of 17d is shown in Figure 3 [38]. Single crystals suitable for X-ray analysis of complexes 17d were obtained by slow evaporation of a mixture of dichloromethane and diethyl ether at about −4 °C. Crystallographic data and structure refinement parameters for 17d are

Preparation and X-ray structure of 2-iodoxybenzenesulfonic acid (IBS) – a powerful hypervalent iodine(V) oxidant

• Irina A. Mironova,
• Pavel S. Postnikov,
• Rosa Y. Yusubova,
• Akira Yoshimura,
• Thomas Wirth,
• Viktor V. Zhdankin,
• Victor N. Nemykin and
• Mekhman S. Yusubov

Beilstein J. Org. Chem. 2018, 14, 1854–1858, doi:10.3762/bjoc.14.159

• problems, IBS was previously characterized by 1H and 13C NMR, IR spectroscopy, high-resolution mass spectrometry, and elemental analysis. However, all previously reported attempts to grow single crystals of IBS from methanol or acetonitrile resulted in reduction with the formation of 2

Host–guest complexes of conformationally flexible C-hexyl-2-bromoresorcinarene and aromatic N-oxides: solid-state, solution and computational studies

• Rakesh Puttreddy,
• Ngong Kodiah Beyeh,
• S. Maryamdokht Taimoory,
• Daniel Meister,
• John F. Trant and
• Kari Rissanen

Beilstein J. Org. Chem. 2018, 14, 1723–1733, doi:10.3762/bjoc.14.146

• Discussion Solid-state X-ray crystallography Nine X-ray crystal structures were obtained from BrC6 in combination with twelve PyNO guest molecules. Several attempts to obtain single crystals of BrC6 by itself, 1+BrC6, 2+BrC6 and 9+BrC6 in methanol were unsuccessful. In the following discussions, for example

Synthesis of diamido-bridged bis-pillar[5]arenes and tris-pillar[5]arenes for construction of unique [1]rotaxanes and bis-[1]rotaxanes

• Ying Han,
• Li-Ming Xu,
• Cui-Yun Nie,
• Shuo Jiang,
• Jing Sun and
• Chao-Guo Yan

Beilstein J. Org. Chem. 2018, 14, 1660–1667, doi:10.3762/bjoc.14.142

• feature was obtained in the five single crystals. That is, the longer chain of methyl (ethyl) oxyalkoxybenzoate not only does not inserted in the cavity of the pillar[5]arene to form the pseudo[1]rotaxane, but also does not thread to the cavity of the neighbouring pillar[5]arene to form the supramolecular

A conformationally adaptive macrocycle: conformational complexity and host–guest chemistry of zorb[4]arene

• Liu-Pan Yang,
• Song-Bo Lu,
• Arto Valkonen,
• Fangfang Pan,
• Kari Rissanen and
• Wei Jiang

Beilstein J. Org. Chem. 2018, 14, 1570–1577, doi:10.3762/bjoc.14.134

• the substituents of guests 12+ and 19+ are quite different in view of their electronic properties, they share very similar binding affinities. What is the underlying reason for the response of binding affinities to the electronic substituent effect on the guests? Luckily, single crystals of complexes

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

• Technical University of Ukraine “Igor Sikorsky Kyiv Polytechnic Institute”, 37 Peremohy ave., Kyiv 03056, Ukraine STC ‘‘Institute for Single Crystals’’, National Academy of Sciences of Ukraine, 60 Nauky ave., Kharkiv 61001, Ukraine Department of Inorganic Chemisrtry, V.M. Karasin Kharkiv National University

¹⁵N-Labelling and structure determination of adamantylated azolo-azines in solution

• Sergey L. Deev,
• Alexander S. Paramonov,
• Tatyana S. Shestakova,
• Igor A. Khalymbadzha,
• Oleg N. Chupakhin,
• Julia O. Subbotina,
• Oleg S. Eltsov,
• Pavel A. Slepukhin,
• Vladimir L. Rusinov,
• Alexander S. Arseniev and
• Zakhar O. Shenkarev

Beilstein J. Org. Chem. 2017, 13, 2535–2548, doi:10.3762/bjoc.13.250

• of them, one of the C2' atoms of the adamantane substituent is located approximately in plane with the heterocyclic moiety of the compound. The populations of the two conformational forms in the single crystals of 15a and 15b (4:1 and 17:3, respectively) differ from the populations of the conformers

Synthesis, effect of substituents on the regiochemistry and equilibrium studies of tetrazolo[1,5-a]pyrimidine/2-azidopyrimidines

• Elisandra Scapin,
• Paulo R. S. Salbego,
• Caroline R. Bender,
• Alexandre R. Meyer,
• Anderson B. Pagliari,
• Tainára Orlando,
• Geórgia C. Zimmer,
• Clarissa P. Frizzo,
• Helio G. Bonacorso,
• Nilo Zanatta and
• Marcos A. P. Martins

Beilstein J. Org. Chem. 2017, 13, 2396–2407, doi:10.3762/bjoc.13.237

• obtaining single crystals The single crystals of the compounds were obtained by slow evaporation of the solvents at 25 °C. Compounds 6a,b,f,h, and 8i were obtained from the solvent CHCl3. Suitable monocrystals for compounds 6d,e were obtained from solvent mixtures of ethyl acetate and EtOH (3:2). General

Structure–property relationships and third-order nonlinearities in diketopyrrolopyrrole based D–π–A–π–D molecules

• Jan Podlesný,
• Lenka Dokládalová,
• Oldřich Pytela,
• Adam Urbanec,
• Milan Klikar,
• Numan Almonasy,
• Tomáš Mikysek,
• Jaroslav Jedryka,
• Iwan V. Kityk and
• Filip Bureš

Beilstein J. Org. Chem. 2017, 13, 2374–2384, doi:10.3762/bjoc.13.235

• single crystals of α-BiB3O6 provided under the same experimental conditions a THG response of 105 pm2/V2 [42]. Hence, the measured THG values of 15–130 pm2/V2 for DPP derivatives 1–5 are comparable with the know data, some of them even exceeded the reference inorganic material and, therefore, DPP

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

• /CW spectrometer with a microwave frequency around 9.7 GHz. The measurements were performed at a modulation frequency of 100 kHz and a magnetic field modulation amplitude of 0.5 mT. The results are shown in Supporting Information File 1, Figure S21. X-ray crystal structure analysis. Single crystals of

Complexation of molecular clips containing fragments of diphenylglycoluril and benzocrown ethers with paraquat and its derivatives

• Leonid S. Kikot',
• Catherine Yu. Kulygina,
• Alexander Yu. Lyapunov,
• Svetlana V. Shishkina,
• Roman I. Zubatyuk,
• Tatiana Yu. Bogaschenko and
• Tatiana I. Kirichenko

Beilstein J. Org. Chem. 2017, 13, 2056–2067, doi:10.3762/bjoc.13.203

• , Odesa 65080, Ukraine Department of X-ray Diffraction Studies and Quantum Chemistry, SSI ‘‘Institute for Single Crystals’’, National Academy of Sciences of Ukraine, Nauky Ave. 60, Kharkiv 61001, Ukraine Department of Inorganic Chemistry, V.N. Karazin Kharkiv National University, 4 Svobody Sq., 61122

NHC-catalyzed cleavage of vicinal diketones and triketones followed by insertion of enones and ynones

• Ken Takaki,
• Makoto Hino,
• Akira Ohno,
• Kimihiro Komeyama,
• Hiroto Yoshida and
• Hiroshi Fukuoka

Beilstein J. Org. Chem. 2017, 13, 1816–1822, doi:10.3762/bjoc.13.176

• crystalline product 12 in 92% yield (Scheme 6). Although 12 did not provide single crystals suitable for X-ray analysis, its structure was determined by NMR and elemental analysis. 1H NMR spectra of 12 showed eleven protons in the aromatic region, i.e., two ClC6H4, Me3C6H2, and one particular proton at δ 6.68

Molecular recognition of N-acetyltryptophan enantiomers by β-cyclodextrin

• Spyros D. Chatziefthimiou,
• Mario Inclán,
• Petros Giastas,
• Athanasios Papakyriakou,
• Konstantina Yannakopoulou and
• Irene M. Mavridis

Beilstein J. Org. Chem. 2017, 13, 1572–1582, doi:10.3762/bjoc.13.157

• solution of β-CD (6 mM) an equimolar quantity of L-NAcTrp was added and stirred for an hour until the solution became clear, which indicated formation of a complex. Then the solution was placed in an incubator at 23 °C, where by slow evaporation of the solvent, single crystals appropriate for X-ray data

• collection were obtained. The crystals had a diamond shape and a slightly pink color. Crystallisation trials of β-CD–D-NAcTrp. Trials to crystallize the complex of β-CD with D-NAcTrp under various conditions, including the above, did not result to single crystals of the complex. D-NAcTrp in the presence of β

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

• performed by using the Suzuki–Miyaura cross-coupling reaction with phenylboronic acid under Pd catalysis (Scheme 5). The location of the formyl group and bromine atoms in ICZ derivatives 12 and 13 has been established by X-ray crystallography analysis, performed for single crystals of 12b and 13b (Figure 5

Glycoscience@Synchrotron: Synchrotron radiation applied to structural glycoscience

• Serge Pérez and
• Daniele de Sanctis

Beilstein J. Org. Chem. 2017, 13, 1145–1167, doi:10.3762/bjoc.13.114

• diffraction had failed. Despite many attempts, the best crystals ever obtained for cellotriose and cellotetraose were very thin laths having dimensions of only about 10 µm in thickness. In the case of cellotetraose, single crystals as small as 0.40 × 0.15 × 0.015 mm could be processed by an X-ray synchrotron

• )-molecules have been revealed, from molecular single crystals all the way to the complexity

New tricks of well-known aminoazoles in isocyanide-based multicomponent reactions and antibacterial activity of the compounds synthesized

• Maryna V. Murlykina,
• Maryna N. Kornet,
• Sergey M. Desenko,
• Svetlana V. Shishkina,
• Oleg V. Shishkin,
• Aleksander A. Brazhko,
• Vladimir I. Musatov,
• Erik V. Van der Eycken and
• Valentin A. Chebanov

Beilstein J. Org. Chem. 2017, 13, 1050–1063, doi:10.3762/bjoc.13.104

• Maryna V. Murlykina Maryna N. Kornet Sergey M. Desenko Svetlana V. Shishkina Oleg V. Shishkin Aleksander A. Brazhko Vladimir I. Musatov Erik V. Van der Eycken Valentin A. Chebanov Division of Chemistry of Functional Materials, State Scientific Institution “Institute for Single Crystals” of

Inclusion complexes of β-cyclodextrin with tricyclic drugs: an X-ray diffraction, NMR and molecular dynamics study

• Franca Castiglione,
• Fabio Ganazzoli,
• Luciana Malpezzi,
• Andrea Mele,
• Walter Panzeri and
• Giuseppina Raffaini

Beilstein J. Org. Chem. 2017, 13, 714–719, doi:10.3762/bjoc.13.70

• comparison of the X-ray structure and the MD simulations in water of 2/β-CD complex showed that 2 is present as single conformer in the crystal and in two conformations in the solution state. Materials and Methods X-ray diffraction Single crystals of 1/β-CD and 2/β-CD were obtained after many attempts by

Highly bulky and stable geometry-constrained iminopyridines: Synthesis, structure and application in Pd-catalyzed Suzuki coupling of aryl chlorides

• Yi Lai,
• Zhijian Zong,
• Yujie Tang,
• Weimin Mo,
• Nan Sun,
• Baoxiang Hu,
• Zhenlu Shen,
• Liqun Jin,
• Wen-hua Sun and
• Xinquan Hu

Beilstein J. Org. Chem. 2017, 13, 213–221, doi:10.3762/bjoc.13.24

• -diisopropylphenyl) in the imino motif, displayed significant enhance with the conversion up to 44%. The results in Table 1 and Figure 1 matched well with our proposal that improving the stability of palladium species favored C–Cl bond activation under higher temperature. Single crystals of complex Pd2 were obtained

Dynamics and interactions of ibuprofen in cyclodextrin nanosponges by solid-state NMR spectroscopy

• Monica Ferro,
• Franca Castiglione,
• Nadia Pastori,
• Carlo Punta,
• Lucio Melone,
• Walter Panzeri,
• Barbara Rossi,
• Francesco Trotta and
• Andrea Mele

Beilstein J. Org. Chem. 2017, 13, 182–194, doi:10.3762/bjoc.13.21

• signal intensity in 1H–13C VCT experiments was observed for the first time on single crystals [16][17][18]. It was found that the frequency of oscillation depends on the heteronuclear dipolar coupling b due to the orientation of the single crystal respect to the external magnetic field. Later on, similar

Supramolecular frameworks based on [60]fullerene hexakisadducts

• Andreas Kraft,
• Johannes Stangl,
• Ana-Maria Krause,
• Klaus Müller-Buschbaum and
• Florian Beuerle

Beilstein J. Org. Chem. 2017, 13, 1–9, doi:10.3762/bjoc.13.1

• tested other polar solvents for crystallization in order to strengthen the supramolecular interactions that hold the networks together. For both C3 and C4, we could finally grow single crystals suitable for X-ray diffraction by slow vapor deposition of Et2O into EtOH solutions of both fullerene

• ]+; anal. calcd for C126H84O48: C, 63.96; H, 3.58; found: C, 63.96; H, 3.58. Crystal growth of HFF-2: Single crystals suitable for X-ray diffraction have been obtained by slow vapor deposition of Et2O into a solution of C3 in EtOH. CCDC deposition number: 1498265. Crystal growth of HFF-3: Single crystals