Constrained thermoresponsive polymers – new insights into fundamentals and applications

• Patricia Flemming,
• Alexander S. Münch,
• Andreas Fery and
• Petra Uhlmann

Beilstein J. Org. Chem. 2021, 17, 2123–2163, doi:10.3762/bjoc.17.138

A new and efficient methodology for olefin epoxidation catalyzed by supported cobalt nanoparticles

• Lucía Rossi-Fernández,
• Viviana Dorn and
• Gabriel Radivoy

Beilstein J. Org. Chem. 2021, 17, 519–526, doi:10.3762/bjoc.17.46

• , 240–400 mesh). Thin-layer chromatography (TLC) was performed on precoated silica gel plates (Merck 60, F254, 0.25 mm). Instrumentation and analysis Nuclear magnetic resonance (NMR) spectra were recorded on a Bruker ARX-300 spectrophotometer using CDCl3 as the solvent and tetramethylsilane (TMS) as

¹⁹F NMR as a tool in chemical biology

• Diana Gimenez,
• Aoife Phelan,
• Cormac D. Murphy and
• Steven L. Cobb

Beilstein J. Org. Chem. 2021, 17, 293–318, doi:10.3762/bjoc.17.28

• ]. Furthermore, owing to the lack of naturally-occurring fluorinated compounds, fluorine is a useful probe to investigate structure and mechanism of biological molecules. Central to these studies is fluorine-19 nuclear magnetic resonance spectroscopy (19F NMR), which allows the user to readily visualize changes

Molecular basis for protein–protein interactions

• Brandon Charles Seychell and
• Tobias Beck

Beilstein J. Org. Chem. 2021, 17, 1–10, doi:10.3762/bjoc.17.1

• methods. These methods are summarised in Figure 1. Atomic resolution methods focus on the structure determination of protein complexes and elucidating the PPIs at a near-atomic resolution. Such methods include X-ray crystallography [12], nuclear magnetic resonance (NMR) [13], and cryogenic electron

Naphthalonitriles featuring efficient emission in solution and in the solid state

• Sidharth Thulaseedharan Nair Sailaja,
• Iván Maisuls,
• Jutta Kösters,
• Alexander Hepp,
• Andreas Faust,
• Jens Voskuhl and
• Cristian A. Strassert

Beilstein J. Org. Chem. 2020, 16, 2960–2970, doi:10.3762/bjoc.16.246

• characterized by nuclear magnetic resonance spectroscopy (NMR, Supporting Information File 1, Figures S1–S24) as well as exact electrospray mass spectrometry (EM–ESIMS, Supporting Information File 1, Figures S25–S30) and appear as white to faint yellow solids. Only the dimethylamino-substituted product shows a

Leveraging glycomics data in glycoprotein 3D structure validation with Privateer

• Haroldas Bagdonas,
• Daniel Ungar and
• Jon Agirre

Beilstein J. Org. Chem. 2020, 16, 2523–2533, doi:10.3762/bjoc.16.204

• glycoproteins Several experimental techniques can be used to obtain 3D structures of glycoproteins: X-ray crystallography (MX, which stands for macromolecular crystallography), nuclear magnetic resonance spectroscopy (NMR) and electron cryomicroscopy (cryo-EM). As of publication date, the overwhelming majority

• and the chain length. However, the in-depth analysis of a glycan typically requires the integration of complementary analytic techniques, such as nuclear magnetic resonance (NMR) and capillary electrophoresis (CE). Nevertheless, depending on the sample, advanced mass spectrometry techniques can be

Computational tools for drawing, building and displaying carbohydrates: a visual guide

• Kanhaya Lal,
• Rafael Bermeo and
• Serge Perez

Beilstein J. Org. Chem. 2020, 16, 2448–2468, doi:10.3762/bjoc.16.199

• areas of chemical and biochemical fragmentations followed by analysis using mass spectroscopy, nuclear magnetic resonance, crystallography and computational modelling. There have been some initiatives by independent research groups worldwide, that pushed the development of visual tools to improve some

Development of fluorinated benzils and bisbenzils as room-temperature phosphorescent molecules

• Shigeyuki Yamada,
• Takuya Higashida,
• Yizhou Wang,
• Masato Morita,
• Takuya Hosokai,
• Kaveendra Maduwantha,
• Kaveenga Rasika Koswattage and
• Tsutomu Konno

Beilstein J. Org. Chem. 2020, 16, 1154–1162, doi:10.3762/bjoc.16.102

• . Interestingly, stirring 1a in DMSO solution in the presence of 30 mol % of PdCl2 at 140 °C for 17 h produced two products (56% yield for the more polar product and 37% yield for the less polar product) after purification with column chromatography. Spectroscopic analyses (i.e., 1H, 19F, and 13C nuclear magnetic

• resonance (NMR) spectroscopy, infrared spectroscopy, and high-resolution mass spectrometry) successfully identified the more polar product as the half-oxidized benzil 2a and the less polar one as the fully oxidized bisbenzil 3a. Fluorinated bistolane 1b, bearing a hexyloxy chain, also underwent PdCl2

Synthesis of novel multifunctional carbazole-based molecules and their thermal, electrochemical and optical properties

• Nuray Altinolcek,
• Ahmet Battal,
• Mustafa Tavasli,
• William J. Peveler,
• Holly A. Yu and
• Peter J. Skabara

Beilstein J. Org. Chem. 2020, 16, 1066–1074, doi:10.3762/bjoc.16.93

• . Inert reactions were performed under an argon atmosphere. Nuclear magnetic resonance (NMR) spectra were obtained on an Agilent Premium Compact NMR spectrometer (600 MHz for 1H NMR, 150 MHz for 13C NMR) with tetramethylsilane as internal standard. Elemental analysis was performed on a Costech Elemental

Accelerating fragment-based library generation by coupling high-performance photoreactors with benchtop analysis

• Quentin Lefebvre,
• Christophe Salomé and
• Thomas C. Fessard

Beilstein J. Org. Chem. 2020, 16, 982–988, doi:10.3762/bjoc.16.87

• coupled to benchtop analysis tools, namely thin-layer chromatography–mass spectrometry (TLC–MS, purchased from https://www.advion.com/rsc-product-note/direct-mass-analysis-of-tlc-plates/) and low-field nuclear magnetic resonance (NMR, purchased from https://www.nanalysis.com/) analysis (Scheme 1). To

Six-fold C–H borylation of hexa-peri-hexabenzocoronene

• Mai Nagase,
• Kenta Kato,
• Akiko Yagi,
• Yasutomo Segawa and
• Kenichiro Itami

Beilstein J. Org. Chem. 2020, 16, 391–397, doi:10.3762/bjoc.16.37

• JEOL JMS-S3000 SpiralTOF (MALDI–TOF MS). Nuclear magnetic resonance (NMR) spectra were recorded on a JEOL ECS-600 (1H 600 MHz, 13C 150 MHz) spectrometer or a JEOL ECA 600II spectrometer with UltraCoolTM probe (1H 600 MHz, 13C 150 MHz). Chemical shifts for 1H NMR are expressed in parts per million (ppm

Synthesis and circularly polarized luminescence properties of BINOL-derived bisbenzofuro[2,3-b:3’,2’-e]pyridines (BBZFPys)

• Ryo Takishima,
• Yuji Nishii,
• Tomoaki Hinoue,
• Yoshitane Imai and
• Masahiro Miura

Beilstein J. Org. Chem. 2020, 16, 325–336, doi:10.3762/bjoc.16.32

• Counter Solvent Dispending System (Nikko Hansen & Co., Ltd.). DMSO was distilled from CaH2 and stored over molecular sieves 4 Å. Silica gel column chromatography was performed using Wakosil® C-200 (64–210 μm). Nuclear magnetic resonance spectra were measured at 400 MHz (1H NMR) and at 100 MHz (13C NMR) in

Synthesis of 4-(2-fluorophenyl)-7-methoxycoumarin: experimental and computational evidence for intramolecular and intermolecular C–F···H–C bonds

• Vuyisa Mzozoyana,
• Fanie R. van Heerden and
• Craig Grimmer

Beilstein J. Org. Chem. 2020, 16, 190–199, doi:10.3762/bjoc.16.22

• gel 60, 0.040–0.063 mm) or centrifugal chromatography conducted on a Harrison Research Chromatotron model 7924T (glass plates coated with silica gel 60 PF254 containing gypsum, 2 and 4 mm thick layer) was used. Nuclear magnetic resonance (NMR) spectra were recorded on a Bruker Avance 400 spectrometer

Safe and highly efficient adaptation of potentially explosive azide chemistry involved in the synthesis of Tamiflu using continuous-flow technology

• Cloudius R. Sagandira and
• Paul Watts

Beilstein J. Org. Chem. 2019, 15, 2577–2589, doi:10.3762/bjoc.15.251

• appropriate drying agents. Nuclear magnetic resonance (NMR) spectra were recorded at room temperature as solutions in deuterated chloroform (CDCl3). A Bruker Avance-400 spectrometer (400 MHz) was used to record the spectra and the chemical shifts are reported in parts per million (ppm) with coupling constants

Synthesis and conformational preferences of short analogues of antifreeze glycopeptides (AFGP)

• Małgorzata Urbańczyk,
• Michał Jewgiński,
• Joanna Krzciuk-Gula,
• Jerzy Góra,
• Rafał Latajka and
• Norbert Sewald

Beilstein J. Org. Chem. 2019, 15, 1581–1591, doi:10.3762/bjoc.15.162

• conformation of the molecule as well an on the stereochemistry of amino acid residues. The desired monoglycosylated analogues with acetylated amino termini and the carboxy termini in form of N-methylamide have been synthesized. Conformational nuclear magnetic resonance (NMR) studies of the designed analogues

• . We assume that ʟ-configured AFGP analogues may exhibit antifreeze activity due to their higher flexibility, hence they can expose more ice-binding groups onto the ice surface, therefore, the amphipathic character of AFGPs might play a crucial role in their activity. Experimental Nuclear magnetic

• resonance NMR spectra were recorded on a Bruker AMX600 spectrometer in deuterated dimethyl sulfoxide (DMSO-d6) at 298 K. Chemical shifts are given in ppm, relative to residual solvent signals (δH = 2.49 ppm, δC = 39.0 ppm). NMR spectral signal assignment and integration were carried out with Bruker TopSpin

Synthesis of aryl cyclopropyl sulfides through copper-promoted S-cyclopropylation of thiophenols using cyclopropylboronic acid

• Emeline Benoit,
• Ahmed Fnaiche and
• Alexandre Gagnon

Beilstein J. Org. Chem. 2019, 15, 1162–1171, doi:10.3762/bjoc.15.113

• indicated solvent system according to standard techniques. Proton nuclear magnetic resonance spectra were recorded on a 300 or 600 MHz spectrometer. Chemical shifts for 1H NMR spectra are recorded in parts per million from tetramethylsilane with the solvent resonance as the internal standard (chloroform, δ

Extending mechanochemical porphyrin synthesis to bulkier aromatics: tetramesitylporphyrin

• Qiwen Su and
• Tamara D. Hamilton

Beilstein J. Org. Chem. 2019, 15, 1149–1153, doi:10.3762/bjoc.15.111

• recorded on a Varian 300 MHz nuclear magnetic resonance spectrometer. Mechanochemical synthesis meso-Tetrakis[2,4,6-(trimethyl)phenyl]porphyrin. Equimolar amounts of pyrrole (0.259 g, 3.75 mmol) and 2,4,6-trimethylbenzaldehyde (0.556 g, 3.75 mmol) were placed in a 10 mL stainless steel grinding jar along

Easy, efficient and versatile one-pot synthesis of Janus-type-substituted fullerenols

• Marius Kunkel and
• Sebastian Polarz

Beilstein J. Org. Chem. 2019, 15, 901–905, doi:10.3762/bjoc.15.87

• via a 13C magic angle spinning nuclear magnetic resonance spectroscopy (MAS NMR) 1H-13C-CP experiment. An overall information of the compound is obtained by attenuated total reflection infrared spectroscopy (ATR-IR). Figure 1 shows the results of the characterization exemplarily for the fullerenol

Photochemical generation of the 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) radical from caged nitroxides by near-infrared two-photon irradiation and its cytocidal effect on lung cancer cells

• Ayato Yamada,
• Manabu Abe,
• Yoshinobu Nishimura,
• Shoji Ishizaka,
• Masashi Namba,
• Taku Nakashima,
• Kiyofumi Shimoji and
• Noboru Hattori

Beilstein J. Org. Chem. 2019, 15, 863–873, doi:10.3762/bjoc.15.84

• sciences. These applications include spin-labels [5][6][7], fluorophore-nitroxide probes [8], contrast agents in magnetic resonance imaging (MRI) [9], polarization transfer agents for nuclear magnetic resonance (NMR) [10][11][12][13], and radical batteries [14][15]. Furthermore, the efficient synthesis of

Study on the regioselectivity of the N-ethylation reaction of N-benzyl-4-oxo-1,4-dihydroquinoline-3-carboxamide

• Pedro N. Batalha,
• Luana da S. M. Forezi,
• Maria Clara R. Freitas,
• Nathalia M. de C. Tolentino,
• Ednilsom Orestes,
• José Walkimar de M. Carneiro,
• Fernanda da C. S. Boechat and
• Maria Cecília B. V. de Souza

Beilstein J. Org. Chem. 2019, 15, 388–400, doi:10.3762/bjoc.15.35

• regioselective manner, without the formation of any byproduct derived from the N-alkylation of the amide group. Structural characterization Table 1 gives the nuclear magnetic resonance spectroscopic data that allowed to confirm the structures of substances 5 and 7, and thus also confirmed the regioselectivity of

Synthesis of C₃-symmetric star-shaped molecules containing α-amino acids and dipeptides via Negishi coupling as a key step

• Sambasivarao Kotha and
• Saidulu Todeti

Beilstein J. Org. Chem. 2019, 15, 371–377, doi:10.3762/bjoc.15.33

• , respectively. Infrared (IR) spectra were recorded on a Nicolet Impact-400 FTIR spectrometer. Specific rotation experiments were measured at 589 nm (Na) and 25 °C (HPLC, CHCl3 stabilized with 0.7–1.0% ethanol). Proton nuclear magnetic resonance (1H NMR, 400 MHz and 500 MHz) spectra and carbon nuclear magnetic

• resonance (13C NMR, 100 MHz and 125 MHz) spectra were recorded on a Bruker spectrometer. The high-resolution mass measurements were carried out by using electrospray ionization (ESI) spectrometer. Melting points were recorded on a Veego melting point apparatus. Negishi coupling product 10 Zinc (Zn) dust was

Metal-free C–H mercaptalization of benzothiazoles and benzoxazoles using 1,3-propanedithiol as thiol source

• Yan Xiao,
• Bing Jing,
• Xiaoxia Liu,
• Hongyu Xue and
• Yajun Liu

Beilstein J. Org. Chem. 2019, 15, 279–284, doi:10.3762/bjoc.15.24

• reaction mixture by proton nuclear magnetic resonance spectroscopy showed that no byproduct was formed. It should be noted that the length of aliphatic dithiols had a significant effect on the reaction performance. The reaction with 1,3-propanedithiol (2b) showed the best reaction performance, providing 3a

Catalysis of linear alkene metathesis by Grubbs-type ruthenium alkylidene complexes containing hemilabile α,α-diphenyl-(monosubstituted-pyridin-2-yl)methanolato ligands

• Tegene T. Tole,
• Johan H. L. Jordaan and
• Hermanus C. M. Vosloo

Beilstein J. Org. Chem. 2019, 15, 194–209, doi:10.3762/bjoc.15.19

• and 5d Proton nuclear magnetic resonance spectrometry (1H NMR) is a powerful tool to study ruthenium alkylidene complexes and was used to study 1-octene metathesis in the presence of 1 and 2 [10][21][22]. The conversion of the benzylidene, [Ru]=CHPh, to the heptylidene, [Ru]=CHC6H13, and methylidene

Mechanistic studies of an L-proline-catalyzed pyridazine formation involving a Diels–Alder reaction with inverse electron demand

• Anne Schnell,
• J. Alexander Willms,
• S. Nozinovic and
• Marianne Engeser

Beilstein J. Org. Chem. 2019, 15, 30–43, doi:10.3762/bjoc.15.3

• from the enamine/dienophile I and the tetrazine. Thus, we decided to use NMR (nuclear magnetic resonance) spectroscopy and ESI mass spectrometry in combination with a charge-tagging strategy to get deeper insights in the presence or absence of the three intermediates by experimental means. Results and

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

• ) and monosubstituted tetrahydro-7H-benzo[7]annulenone, St-Jacques' group benefited extensively from the use of dynamic nuclear magnetic resonance (DNMR) techniques [126][127]. A catalytic deuterogenation of 4,5-benzotropone (11) followed by deuteration led to deuterated 5,6,8,9-tetrahydro-7H-benzo[7