Diastereoselective synthesis of 3,4-dihydro-2H-pyran-4-carboxamides through an unusual regiospecific quasi-hydrolysis of a cyano group

• Mikhail Yu. Ievlev,
• Oleg V. Ershov,
• Mikhail Yu. Belikov,
• Angelina G. Milovidova,
• Viktor A. Tafeenko and
• Oleg E. Nasakin

Beilstein J. Org. Chem. 2016, 12, 2093–2098, doi:10.3762/bjoc.12.198

• all new compounds. Acknowledgements This work was supported by a stipend of the President of the Russian Federation for young scientists and graduate students (SP-127.2016.4). The XRD study was carried out using the equipment purchased from the funds of the program of development of the Moscow

Cross-linked cyclodextrin-based material for treatment of metals and organic substances present in industrial discharge waters

• Élise Euvrard,
• Nadia Morin-Crini,
• Coline Druart,
• Justine Bugnet,
• Bernard Martel,
• Cesare Cosentino,
• Virginie Moutarlier and
• Grégorio Crini

Beilstein J. Org. Chem. 2016, 12, 1826–1838, doi:10.3762/bjoc.12.172

• . The point of zero charge (PZC) was plotted and followed the linear equations y = −0.9639x + 6.1422 and y = −0.9233x + 3.138 indicating a pH of 6.4 and 3.4 for the PZC of activated and non-activated polyBTCA-CD, respectively (Figure 2). Figure 3 shows the XRD pattern of non-activated and activated

• then the resulting pH (pHf) was measured. The difference between the initial and final pH values (ΔpH) was plotted against the initial pH. The PZC was represented by the point ΔpH = 0 [32]. X-ray diffraction analysis (XRD) was performed on a Bruker D8 Advance diffractometer using Cu Kα radiation with a

• wavelength of λ = 0.15406 nm produced at 40 kV and 40 mA. XRD data were collected over the 2θ range from 10° to 60° at every 0.02° with a scan speed of 0.5 s per step. For polymer, the diffraction profiles are divided into 2 parts: peaks related to diffraction of crystallites and a broad peak related to

Syntheses of dibenzo[d,d']benzo[2,1-b:3,4-b']difuran derivatives and their application to organic field-effect transistors

• Minh Anh Truong and
• Koji Nakano

Beilstein J. Org. Chem. 2016, 12, 805–812, doi:10.3762/bjoc.12.79

• anti-DNBDF derivatives [39]. Analysis of thin films The vapor-deposited thin films of syn-DBBDF 5 and syn-DNBDF 6 were analyzed by X-ray diffraction (XRD) and atomic force microscopy (AFM). Figure 6 shows the out-of-plane XRD pattern and an AFM image of the thin film of syn-DNBDF 6 on the HMDS-treated

• ) along with heterogeneous protrusions. The molecular arrangement indicated by these observations is advantageous for the in-plane charge transfer of OFETs. Based on XRD patterns and AFM images, the substrate treatment and the substrate temperature seem to have a limited impact on the molecular

• M Bu4NClO4; Pt as working and counter electrodes; scan rate = 50 mV·s−1). Output and transfer characteristics of the representative OFETs with a thin film of (a) syn-DBBDF 5 (Tsub = 30 °C) and (b) syn-DNBDF 6 (Tsub = 90 °C) on HMDS-treated Si/SiO2 substrates. (a) XRD pattern, (b) AFM image (2 × 2 μm

Urethane tetrathiafulvalene derivatives: synthesis, self-assembly and electrochemical properties

• Xiang Sun,
• Guoqiao Lai,
• Zhifang Li,
• Yuwen Ma,
• Xiao Yuan,
• Yongjia Shen and
• Chengyun Wang

Beilstein J. Org. Chem. 2015, 11, 2343–2349, doi:10.3762/bjoc.11.255

• microscopy (SEM) and X-ray diffraction (XRD), which showed that the self-assembly ability of T1 was better than that of T2. The results revealed that more urethane groups in a molecule did not necessarily instigate self-assembly. UV–vis and FTIR spectra were measured to explore noncovalent interactions. The

• nanoribbons was approximately 500 nm with a length of >20 μm. Although nanoribbons were observed in the SEM images of T2 (Figure 2b), they showed no similar ordered structure. In addition, the X-ray diffraction (XRD) patterns of T1 and T2 nanoribbons were taken (Supporting Information File 1, Figure S7). The

• XRD pattern of T1 showed three sharp peaks at 7.4°, 14.9° and 22.1°, which suggested that a lamellar stacking organization was formed [4]. This was not the case for the XRD pattern of T2. In general, intermolecular hydrogen bonding is the main driving force behind self-assembly. Although T2 contains

Ru complexes of Hoveyda–Grubbs type immobilized on lamellar zeolites: activity in olefin metathesis reactions

• Hynek Balcar,
• Naděžda Žilková,
• Martin Kubů,
• Michal Mazur,
• Zdeněk Bastl and
• Jiří Čejka

Beilstein J. Org. Chem. 2015, 11, 2087–2096, doi:10.3762/bjoc.11.225

• decomposition of the PF6− anion and ligand exchange at the Ru atom most likely accompanied the immobilization. The XRD and nitrogen adsorption measurements confirmed that the layered structure of the supports was preserved in the prepared hybrid catalysts. The activity of hybrid catalysts was studied (i) in RCM

• samples were degassed on a Micromeritics FlowPrep060 instrument under helium at 110 °C for 6 h. X-ray powder diffraction (XRD) data were obtained on a Bruker AXS D8 Advance diffractometer with a graphite monochromator and a Vantec-1 position sensitive detector using Cu Kα radiation (at 40 kV and 30 mA) in

• for preparation of hybrid catalysts. Supporting Information Supporting Information File 504: XRD patterns of catalysts and supports, conversion curves for self-metatheses of methyl oleate and cis-3-hexenyl acetate, splitting experiment. Acknowledgements The authors thank K. Skowerski (Apeiron

Investigation of the role of stereoelectronic effects in the conformation of piperidones by NMR spectroscopy and X-ray diffraction

• Cesar Garcias-Morales,
• David Ortegón-Reyna and
• Armando Ariza-Castolo

Beilstein J. Org. Chem. 2015, 11, 1973–1984, doi:10.3762/bjoc.11.213

• is absent in compounds 3–8. The solid-state conformations of the piperidones were determined by X-ray diffraction (XRD). Crystals of 1, 3, 5, 6, and 7 suitable for XRD were obtained. The crystal structures of 3 and 5 have been previously reported [47][61][62][63]. The crystal structures of 1, 6, and

• in the structures obtained by XRD. Proposed reaction mechanism for the synthesis of piperidones by the Mannich reaction. The substituents are shown in Figure 4. For 6, R1 = R2 = H, for 7, R1 = H, R2 = CH3, for 8, R1 = R2 = CH3. Representation of the nN→σ*C–H(7)eq interaction. The interaction energy

Star-shaped tetrathiafulvalene oligomers towards the construction of conducting supramolecular assembly

• Masahiko Iyoda and
• Masashi Hasegawa

Beilstein J. Org. Chem. 2015, 11, 1596–1613, doi:10.3762/bjoc.11.175

• waves corresponding to the formation of 4410+ and 4420+. Trisubstituted 38 showed polymorphism and formed single crystals from CH2Cl2, whereas it produced a yellow fibrous material from CH2Cl2–hexane 1:4. X-ray diffractometry (XRD) exhibited that fiber 38 possesses a hexagonal columnar structure

• formed by casting a solution of 48 on a glass surface (Figure 17c). XRD studies on the fiber and the film of 48 revealed that the fiber has a hexagonal alignment, whereas the film has a lamellar structure with lateral order and π···π stacking. It is worth noting that the film of 48 prepared by casting a

• = 3.1 × 10-5 S cm−1) depending on their stacking structures. Cation radicals of pyrrole-fused TTF trimer 38 also formed conducting nanostructures when a CH2Cl2 solution of 381.5(•+) was mixed with an excess amount of hexane. The XRD pattern of the fiber 381.5(•+) is composed of a lamellar structure

Synthesis of photoresponsive cholesterol-based azobenzene organogels: dependence on different spacer lengths

• Yuchun Ren,
• Bin Wang and
• Xiuqing Zhang

Beilstein J. Org. Chem. 2015, 11, 1089–1095, doi:10.3762/bjoc.11.122

• the aggregates change from flower-like, network and rod with different sizes. By using IR and XRD characterization, it is found that intermolecular H-bonding, the solvents and van der Waals interaction are the main contributions to the specific superstructure. Keywords: azobenzene; cholesterol

• shifted to 2933 and 2859 cm−1. The above mentioned FTIR spectral changes demonstrated sufficiently that van der Waals interaction between the alkyl chains plays an important role in the self-assembly process of organogels. The XRD studies To reveal the detailed changes in gel molecular of M6, XRD analyses

• another two solvents, corresponding to d values of 5.10 and 3.50 nm, respectively. The different self-assembly modes of gelator in various solvents cause the values changing. The XRD results described above also demonstrated that the molecular interaction and the solvents had a significant impact on the

Tuning the size of a redox-active tetrathiafulvalene-based self-assembled ring

• Sébastien Bivaud,
• Sébastien Goeb,
• Vincent Croué,
• Magali Allain,
• Flavia Pop and
• Marc Sallé

Beilstein J. Org. Chem. 2015, 11, 966–971, doi:10.3762/bjoc.11.108

• crystal structure of self-assembly M6L3. For clarity, H atoms and TfO− counteranions have been omitted. Geometry (from XRD) around two Pd centers in M4L2 (a) and M6L3 (b). The exTTF moieties have been cut for clarity. Cyclic voltammogram of L1 (c = 10−3 M, CH3CN/CH2Cl2 (v/v 50/50), 0.1 M n-Bu4NPF6, 100

Synthesis of tripodal catecholates and their immobilization on zinc oxide nanoparticles

• Franziska Klitsche,
• Julian Ramcke,
• Julia Migenda,
• Andreas Hensel,
• Tobias Vossmeyer,
• Horst Weller,
• Silvia Gross and
• Wolfgang Maison

Beilstein J. Org. Chem. 2015, 11, 678–686, doi:10.3762/bjoc.11.77

• diffraction to confirm the formation of crystalline materials. The XRD pattern confirms the selective formation of pure ZnO wurtzite already at room temperature without the need of any further thermal treatment (Figure 3A). This data is in agreement with TEM micrographs, indicating the presence of spherical

• water (pH 7) and MeOH and freeze-dried before analysis by XRD, IR, HRTEM-EDX and TGA. A reference probe of ZnO NPs was treated the same way, but no catecholate was added to the buffer. 3-Morpholinopropanesulfonate, the ingredient of the MOPS buffer, showed only a weak affinity for ZnO NPs according to

• 100 kV. HRTEM and EDX analysis For high resolution TEM (HRTEM) and energy-dispersive X-ray analysis (EDX), the functionalized particles were dispersed in MeOH and transferred to carbon-coated TEM grids. The samples were analyzed using a Philips CM 300 microscope, operated at 300 kV. XRD analysis For

Direct access to pyrido/pyrrolo[2,1-b]quinazolin-9(1H)-ones through silver-mediated intramolecular alkyne hydroamination reactions

• Hengshuai Wang,
• Shengchao Jiao,
• Kerong Chen,
• Xu Zhang,
• Linxiang Zhao,
• Dan Liu,
• Yu Zhou and
• Hong Liu

Beilstein J. Org. Chem. 2015, 11, 416–424, doi:10.3762/bjoc.11.47

• . Products 7A and 9G were recrystallized and their structures were unambiguously confirmed by X-ray diffraction (XRD) studies (see Supporting Information File 1 for details). Conclusion In conclusion, we have developed a chemical methodology for the synthesis of pyrido/pyrrolo[2,1-b]quinazolin-9(1H)-ones

First chemoenzymatic stereodivergent synthesis of both enantiomers of promethazine and ethopropazine

• Paweł Borowiecki,
• Daniel Paprocki and
• Maciej Dranka

Beilstein J. Org. Chem. 2014, 10, 3038–3055, doi:10.3762/bjoc.10.322

• found as ideal biocatalysts for preparation of highly enantioenriched phenothiazolic alcohols (up to >99% ee), which absolute configurations were assigned by Mosher’s methodology and unambiguously confirmed by XRD analysis. Thus obtained key-intermediates were further transformed into bromide

• which the (R)-enantiomer of the chiral substrate (±)-3 is preferentially acetylated. In order to unambiguously confirm the adequacy of 1H NMR shift analysis, the single crystal of enantiomerically pure alcohol (+)-5 (>99% ee) was subsequently analyzed by X-ray diffraction (XRD) method (Figure 4), which

• confirmed (S)-configuration and allowed us to conclude that Mosher’s methodology can serve as a reliable determination method of the absolute configuration toward this type of compounds. For details concerning crystallization procedure and XRD measurements see Supporting Information File 1. Approaches to

Thermal and oxidative stability of the Ocimum basilicum L. essential oil/β-cyclodextrin supramolecular system

• Daniel I. Hădărugă,
• Nicoleta G. Hădărugă,
• Corina I. Costescu,
• Ioan David and
• Alexandra T. Gruia

Beilstein J. Org. Chem. 2014, 10, 2809–2820, doi:10.3762/bjoc.10.298

• formation was determined by thermal analysis (TG, DSC), FTIR and XRD. The quality of the encapsulation has been studied by gas chromatographic methods. Methylchavicol and other structurally related volatiles were also encapsulated in various natural CDs such as α- and β-CD, as well as in semisynthetic

Improving the reactivity of phenylacetylene macrocycles toward topochemical polymerization by side chains modification

• Simon Rondeau-Gagné,
• Jules Roméo Néabo,
• Maxime Daigle,
• Katy Cantin and
• Jean-François Morin

Beilstein J. Org. Chem. 2014, 10, 1613–1619, doi:10.3762/bjoc.10.167

• the xerogel state to form polydiacetylenes (PDAs), leading to a significant enhancement of the polymerization yields. The organogels and the PDAs were characterized using Raman spectroscopy, X-ray diffraction (XRD) and scanning electron microscopy (SEM). Keywords: carbon nanomaterials; organogels

• some insights on the molecular packing within the assembly, X-ray diffraction (XRD) was performed on PAM2 (see Figure S21 in Supporting Information File 1). Unlike PAM1, the presence of a columnar arrangement cannot be established from the diffractogram [31][39]. Instead, only a broad peak at 2θ = 20

• PAM scaffold (≈15% yield). This result suggests that the diyne units in PAM2 are in a more suitable orientation than PAM1 to undergo a topochemical polymerization, although gelation properties and XRD result seem to suggest otherwise. It is also possible that the apparent yield increase comes from a

Unusual polymorphism in new bent-shaped liquid crystals based on biphenyl as a central molecular core

• Anna Kovářová,
• Svatopluk Světlík,
• Václav Kozmík,
• Jiří Svoboda,
• Vladimíra Novotná,
• Damian Pociecha,
• Ewa Gorecka and
• Natalia Podoliak

Beilstein J. Org. Chem. 2014, 10, 794–807, doi:10.3762/bjoc.10.75

• voltage from a Phillips generator PM 5191 accompanied by a linear amplifier providing a maximum amplitude of about ±120 V. A Tektronix TDC70 memory oscilloscope was used to display information about switching current profile vs. time. X-ray diffraction studies (XRD) were performed using a Bruker Nanostar

Triphenylene discotic liquid crystal trimers synthesized by Co₂(CO)₈-catalyzed terminal alkyne [2 + 2 + 2] cycloaddition

• Bin Han,
• Ping Hu,
• Bi-Qin Wang,
• Carl Redshaw and
• Ke-Qing Zhao

Beilstein J. Org. Chem. 2013, 9, 2852–2861, doi:10.3762/bjoc.9.321

• with 10 mol % of Co2(CO)8 as the catalyst in refluxing 1,4-dioxane. The liquid crystalline properties were investigated by using polarizing optical microscopy (POM), differential scanning calorimetry (DSC) and X-ray diffraction (XRD). Trimer 4 with an ester connecting group and a longer spacer

• , and the reversed transition at 101 °C on cooling. No crystallization was observed for either 5b or 5c. XRD results Figure 4 depicts the X-ray diffraction patterns of 4, 5b and 5c at room temperature cooling from the isotropic liquid. Both 5b and 5c show a strong diffraction peak in the small-angle

• region (2θ = 3.8° or 4.5°), a broad halo peak of the alkyl chain at ca. 18°, and a core–core distance peak at 3.5–3.7 Å. Considering these XRD results together with their homeotropic alignment behavior displayed by the POM results shown in Figure 2C and Figure 2D, we assigned the mesophase of 5b and 5c

Synthesis of guanidinium–sulfonimide ion pairs: towards novel ionic liquid crystals

• Martin Butschies,
• Manuel M. Neidhardt,
• Markus Mansueto,
• Sabine Laschat and
• Stefan Tussetschläger

Beilstein J. Org. Chem. 2013, 9, 1093–1101, doi:10.3762/bjoc.9.121

• alignment (Figure 2) typical for SmA phases. The mesophase of compound 3b was investigated by X-ray scattering (WAXS and SAXS) at different temperatures. The XRD experiments revealed diffraction patterns with a single diffraction peak and a diffuse halo at 4.7 Å resulting from the alkyl chains (Figure 3

Synthesis and structure of trans-bis(1,4-dimesityl-3-methyl-1,2,3-triazol-5-ylidene)palladium(II) dichloride and diacetate. Suzuki–Miyaura coupling of polybromoarenes with high catalytic turnover efficiencies

• Jeelani Basha Shaik,
• Venkatachalam Ramkumar,
• Babu Varghese and
• Sethuraman Sankararaman

Beilstein J. Org. Chem. 2013, 9, 698–704, doi:10.3762/bjoc.9.79

• dihedral angle of 55.47°. The mesityl rings are also significantly twisted out of plane with respect to the triazolylidene rings in 1 compared to the twist of the phenyl rings in 3. The structure of 2 was also unambiguously established by single-crystal XRD data. Crystals suitable for XRD were grown by

A facile, rapid, one-pot regio/stereoselective synthesis of 2-iminothiazolidin-4-ones under solvent/scavenger-free conditions

• Murugan Sathishkumar,
• Sangaraiah Nagarajan,
• Poovan Shanmugavelan,
• Murugan Dinesh and
• Alagusundaram Ponnuswamy

Beilstein J. Org. Chem. 2013, 9, 689–697, doi:10.3762/bjoc.9.78

• the reaction was very rapid affording the product 4f in 15–20 min (Table 1, entries 7 and 8) compared to 2–6 h (Table 1, entries 1–6) in solvents. The structure of the product 4f was assigned as (Z)-2-(2-phenylcyclohex-2-enylimino)-3-p-tolylthiazolidin-4-one based on the single-crystal XRD data [28

A peptidic hydrogel that may behave as a “Trojan Horse”

• Nicola Castellucci,
• Giorgio Sartor,
• Natalia Calonghi,
• Carola Parolin,
• Giuseppe Falini and
• Claudia Tomasini

Beilstein J. Org. Chem. 2013, 9, 417–424, doi:10.3762/bjoc.9.44

• 10.3762/bjoc.9.44 Abstract A physical hydrogel prepared with the low-molecular-weight hydrogelator (LMWHG) CH2(C3H6CO-L-Phe-D-Oxd-OH)2 and water/ethanol mixture was applied as a potential “Trojan Horse” carrier into cells. By SEM and XRD analysis we could demonstrate that a fibrous structure is present in

• , were analyzed by X-ray diffraction (XRD) and scanning electron microscopy (SEM). Hydrogel 1 is a strong and thermoreversible gel (Figure 1a) with its melting point at 45 °C. The XRD pattern from the hydrogel 1, collected at 100 K, is characterized by the presence of diffraction rings at low angle

• (indicated in Figure 2b) having periodicities of 2.2 nm, 1.7 nm, 1.4 nm and 0.54 nm. The additional high-angle diffraction rings not listed are due to the presence of ice [27]. Any attempt to collect XRD data at room temperature, or at 100 K in the presence of cryoprotectants, to avoid the formation of ice

Iron-containing mesoporous aluminosilicate catalyzed direct alkenylation of phenols: Facile synthesis of 1,1-diarylalkenes

• Satyajit Haldar and
• Subratanath Koner

Beilstein J. Org. Chem. 2013, 9, 49–55, doi:10.3762/bjoc.9.6

• established from the small-angle XRD patterns (see Supporting Information File 1). The BET surface area and the pore width of Fe-Al-MCM-41 were found to be 753 m2/g and 25.83 Å, respectively. The aluminium and iron contents of the Fe-Al-MCM-41 catalyst were estimated by AAS method and found to be 5.5 wt % and

• hydrolysis [48]. The disintegration of the mesoporous structure was achieved by boiling Fe-Al-MCM-41 with millipore water. The liquid-to-sample ratio was fixed at 1 Lg−1. After 12 h of heating, the sample was filtered and dried in an oven for 2 h at 398 K. The XRD patterns of the dried sample revealed that

Self-assembled organic–inorganic magnetic hybrid adsorbent ferrite based on cyclodextrin nanoparticles

• Ângelo M. L. Denadai,
• Frederico B. De Sousa,
• Joel J. Passos,
• Fernando C. Guatimosim,
• Kirla D. Barbosa,
• Ana E. Burgos,
• Fernando Castro de Oliveira,
• Jeann C. da Silva,
• Bernardo R. A. Neves,
• Nelcy D. S. Mohallem and
• Rubén D. Sinisterra

Beilstein J. Org. Chem. 2012, 8, 1867–1876, doi:10.3762/bjoc.8.215

• /Zn and the MHM prepared by using Fe-Ni/Zn and βCD (Fe-Ni/Zn/βCD) were synthesized by adapting a method previously described in the literature [7]. These magnetic materials were characterized in the solid state by X-ray powder diffraction (XRD), Fourier transform infrared spectroscopy (FTIR), and

Liquid-crystalline heterodimesogens and ABA-heterotrimesogens comprising a bent 3,5-diphenyl-1,2,4-oxadiazole central unit

• Govindaswamy Shanker,
• Marko Prehm and
• Carsten Tschierske

Beilstein J. Org. Chem. 2012, 8, 472–485, doi:10.3762/bjoc.8.54

• studied by optical polarizing microscopy (PM), differential scanning calorimetry (DSC) and X-ray diffraction (XRD). All dimesogens exhibit broad ranges of cybotactic nematic phases (NcybA and NcybC), in some cases accompanied by additional mesophases (CybA or SmC) at lower temperature. The combination of

• bent-core mesogens are of special interest for achieving biaxial nematic phases of the orthorhombic type. The orthogonal (NcybA) and skewed (NcybC) cybotactic nematic phases were distinguished by XRD and optical observations. Keywords: bent-core mesogens; cybotactic nematic phases; dimesogen; liquid

• differential scanning calorimetry (DSC, DSC-7, Perkin-Elmer). The assignment of the mesophases is based on the combined results of optical textures and X-ray diffraction (XRD) studies. XRD investigations on aligned samples were performed by using a 2D wire detector (HI-Star, Siemens AG). Alignment was achieved

Liquid-crystalline nanoparticles: Hybrid design and mesophase structures

• Gareth L. Nealon,
• Romain Greget,
• Cristina Dominguez,
• Zsuzsanna T. Nagy,
• Daniel Guillon,
• Jean-Louis Gallani and
• Bertrand Donnio

Beilstein J. Org. Chem. 2012, 8, 349–370, doi:10.3762/bjoc.8.39

• investigations into the integration of bent-core mesogens into new NP hybrids have been reported. An early report investigated the grafting of bent-core ligands 1410,10 and 1412,11 (Figure 18) to hexanethiol coated Au NPs with diameters of 2.8 ± 0.6 and 2.5 ± 0.5 nm by TEM (3.9 ± 1.5 nm and 2.4 ± 0.8 nm by XRD

Continuous preparation of carbon-nanotube-supported platinum catalysts in a flow reactor directly heated by electric current

• Alicja Schlange,
• Antonio Rodolfo dos Santos,
• Ulrich Kunz and
• Thomas Turek

Beilstein J. Org. Chem. 2011, 7, 1412–1420, doi:10.3762/bjoc.7.165

• has much higher dispersion. Powder X-ray diffraction analysis was performed to investigate the crystalline structure of the prepared catalysts and the support material. XRD spectra are given in Figure 5. For pristine carbon nanotubes the diffraction peaks at 30.0° and 50.4° can be attributed to the

• with ethanol, then separated by means of a centrifuge at 4000 rpm and finally dried in a furnace at 60 °C under air flow. Characterization methods The crystalline structures of the support material and electrocatalysts were analyzed by X-ray diffraction (XRD) with a Siemens D5000/Kristalloflex