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

• ). Each independent intermediate was characterized on the basis of its 19F NMR chemical shift and the kinetics by which each species formed or decayed were evaluated in real-time. By combining the 19F NMR data with that provided by complementary analytical techniques, mass spectrometry (electrospray

Control over size, shape, and photonics of self-assembled organic nanocrystals

• Chen Shahar,
• Yaron Tidhar,
• Yunmin Jung,
• Haim Weissman,
• Sidney R. Cohen,
• Ronit Bitton,
• Iddo Pinkas,
• Gilad Haran and
• Boris Rybtchinski

Beilstein J. Org. Chem. 2021, 17, 42–51, doi:10.3762/bjoc.17.5

• applicability of organic nanocrystals. Experimental General information The 1H and 13C NMR spectra were recorded at 20 °C on a 300 MHz NMR spectrometer (Bruker). Electrospray ionization (ESI) mass spectrometry was performed using a Micromass Platform instrument. UV–vis absorption and fluorescence measurements

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

Synthesis of imidazo[1,5-a]pyridines via cyclocondensation of 2-(aminomethyl)pyridines with electrophilically activated nitroalkanes

• Dmitrii A. Aksenov,
• Nikolai A. Arutiunov,
• Vladimir V. Maliuga,
• Alexander V. Aksenov and
• Michael Rubin

Beilstein J. Org. Chem. 2020, 16, 2903–2910, doi:10.3762/bjoc.16.239

• DMSO-d6, using TMS as an internal standard. High-resolution mass spectra were obtained using a Bruker Maxis spectrometer (electrospray ionization, MeCN solution, using HCO2Na/HCO2H for calibration). Melting points were measured with a Stuart smp30 apparatus. All reactions were performed in oven-dried

A heterobimetallic tetrahedron from a linear platinum(II)-bis(acetylide) metalloligand

• Matthias Hardy,
• Marianne Engeser and
• Arne Lützen

Beilstein J. Org. Chem. 2020, 16, 2701–2708, doi:10.3762/bjoc.16.220

• , correlation of the proton. Low- and high-resolution electrospray ionization mass spectrometry (ESIMS) spectra were recorded on a Bruker Daltonic LTQ Orbitrap XL. The UV–vis spectrum was recorded on a Specord 200 spectrometer (Analytik Jena AG) at ambient temperature. 4-Ethynylaniline (1) [50], trans-[Pt(PBu3

Water-soluble host–guest complexes between fullerenes and a sugar-functionalized tribenzotriquinacene assembling to microspheres

• Si-Yuan Liu,
• Xin-Rui Wang,
• Man-Ping Li,
• Wen-Rong Xu and
• Dietmar Kuck

Beilstein J. Org. Chem. 2020, 16, 2551–2561, doi:10.3762/bjoc.16.207

• ppm in the 13C NMR spectrum were attributed to the acetylene protons and carbons, respectively. The electrospray ionization (ESI) mass spectrum showed the most intense peak at m/z 641.1923, which corresponds to the [M + Na]+ molecular adduct ion and matches well with the calculated value (m/z 641.1935

• Instruments Co., Ltd, Shanghai, China). Mass spectra were recorded using either electrospray ionization (ESI) on a LCMS-IT-TOF instrument (Shimadzu, Kyoto, Japan) or a matrix-assisted laser desorption/ionization (MALDI) on a RapifleX MALDI Tissuetyper system (Bruker Daltonik GmbH, Bremen, Germany). Raman

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

• ]. Typically, these analyses are based on mass spectrometry techniques, such as electrospray ionization mass spectrometry (ESIMS) and matrix-assisted laser desorption ionization MS (MALDIMS) [43]. Mass spectrometry techniques are best suited for the determination of the composition of monosaccharide classes

Muyocopronones A and B: azaphilones from the endophytic fungus Muyocopron laterale

• Ken-ichi Nakashima,
• Junko Tomida,
• Tomoe Tsuboi,
• Yoshiaki Kawamura and
• Makoto Inoue

Beilstein J. Org. Chem. 2020, 16, 2100–2107, doi:10.3762/bjoc.16.177

• . NMR spectra were acquired on a JEOL JNM-ECZ 400S spectrometer with tetramethylsilane as the internal standard. ESIMS data were obtained using an Agilent 6230B TOF LC/MS system equipped with an electrospray ion source (Agilent Technologies, CA, USA) and an Agilent 1260 infinity II LC (Agilent

Clustering and curation of electropherograms: an efficient method for analyzing large cohorts of capillary electrophoresis glycomic profiles for bioprocessing operations

• Ian Walsh,
• Matthew S. F. Choo,
• Sim Lyn Chiin,
• Amelia Mak,
• Shi Jie Tay,
• Pauline M. Rudd,
• Yang Yuansheng,
• Andre Choo,
• Ho Ying Swan and
• Terry Nguyen-Khuong

Beilstein J. Org. Chem. 2020, 16, 2087–2099, doi:10.3762/bjoc.16.176

• of m/z 400–2000 was used, with an acquisition speed of 1 Hz, and the mass spectrometry was set at the following conditions: 2.75 kV electrospray ionization capillary voltage, 15 V cone voltage, 120 °C ion source temperature, 300 °C desolvation temperature, 800 L/h desolvation gas flow. A lockspray

Regiodivergent synthesis of functionalized pyrimidines and imidazoles through phenacyl azides in deep eutectic solvents

• Paola Vitale,
• Luciana Cicco,
• Ilaria Cellamare,
• Filippo M. Perna,
• Antonio Salomone and
• Vito Capriati

Beilstein J. Org. Chem. 2020, 16, 1915–1923, doi:10.3762/bjoc.16.158

• mass spectrometer equipped with an electrospray ion source (ESI). NaN3, 2-haloketones, and all other reagents, unless otherwise specified, were purchased from Sigma-Aldrich (Sigma-Aldrich, St. Louis, MO, USA), and used without any further purification. Experimental procedures General procedure for the

Five-component, one-pot synthesis of an electroactive rotaxane comprising a bisferrocene macrocycle

• Natalie Lagesse,
• Luca Pisciottani,
• Maxime Douarre,
• Pascale Godard,
• Brice Kauffmann,
• Vicente Martí-Centelles and
• Nathan D. McClenaghan

Beilstein J. Org. Chem. 2020, 16, 1564–1571, doi:10.3762/bjoc.16.128

• an FD emitter with an emitter voltage of 10 kV. The sample (1–2 µL) was deposited on a 13 μm emitter wire. Electrospray spectra (ESI) were recorded on a Qexactive (Thermo) mass spectrometer. The instrument was equipped with an ESI source and spectra were recorded in the positive mode. The spray

Heterogeneous photocatalysis in flow chemical reactors

• Christopher G. Thomson,
• Ai-Lan Lee and
• Filipe Vilela

Beilstein J. Org. Chem. 2020, 16, 1495–1549, doi:10.3762/bjoc.16.125

• stable HPCat for reductive dehalogenations and cyclisations, and reported its enhanced photocatalytic activity relative to unmodified TiO2 [151]. Electrochemical deposition techniques, such as electrospray and electrospinning, can also be applied to form photocatalytic composite materials. This has been

Synthesis and properties of quinazoline-based versatile exciplex-forming compounds

• Rasa Keruckiene,
• Simona Vekteryte,
• Ervinas Urbonas,
• Matas Guzauskas,
• Eigirdas Skuodis,
• Dmytro Volyniuk and
• Juozas V. Grazulevicius

Beilstein J. Org. Chem. 2020, 16, 1142–1153, doi:10.3762/bjoc.16.101

• occurred by coupling a gas chromatograph and a high-pressure liquid chromatograph. The samples were prepared as dilute solutions of the compounds and were ionized by using electrospray ionization. The mass spectra are presented as an abundance of the ion versus the mass-to-charge ratio (m/z). Melting

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

• system. The IR spectra were obtained (4000–400 cm−1) using a Shimadzu IRAffinity-1S Fourier transform infrared spectrophotometer. The mass spectra were obtained by Bruker microTOFq mass spectrometers to obtain low- and high-resolution spectra using electron ionisation (EI) or electrospray ionisation (ESI

Synthesis of new asparagine-based glycopeptides for future scanning tunneling microscopy investigations

• Laura Sršan and
• Thomas Ziegler

Beilstein J. Org. Chem. 2020, 16, 888–894, doi:10.3762/bjoc.16.80

• cell surfaces for future investigations by combined preparative mass spectroscopy and scanning tunneling microscopy (STM) using soft-landing electrospray beam deposition (ES-IBD), on metal surfaces. Keywords: amino acids; asparagine; carbohydrates; glycopeptides; peptidomimetics; Introduction

Halogen-bonding-induced diverse aggregation of 4,5-diiodo-1,2,3-triazolium salts with different anions

• Xingyu Xu,
• Shiqing Huang,
• Zengyu Zhang,
• Lei Cao and
• Xiaoyu Yan

Beilstein J. Org. Chem. 2020, 16, 78–87, doi:10.3762/bjoc.16.10

• electrospray ionization mode (ESI). Elemental analyses (C, H, N) were performed on Flash EA 1112 Analyzer. Synthesis 2-I: 4,5-Unsubstituted triazolium salt 1 (450 mg, 1 mmol), potassium tert-butoxide (250 mg, 2.2 mmol) and I2 (510 mg, 2 mmol) were added in a Schlenk tube under nitrogen, then THF (20 mL) was

Palladium-catalyzed Sonogashira coupling reactions in γ-valerolactone-based ionic liquids

• László Orha,
• József M. Tukacs,
• László Kollár and
• László T. Mika

Beilstein J. Org. Chem. 2019, 15, 2907–2913, doi:10.3762/bjoc.15.284

• File 1. Exact mass measurements were performed on a high-resolution Q-Exactive Focus hybrid quadrupole-orbitrap mass spectrometer (Thermo Fisher Scientific, Bremen, Germany) equipped with a heated electrospray ionization (ESI) source. Samples were dissolved in acetonitrile/water 1:1 (v/v) solvent

Photoreversible stretching of a BAPTA chelator marshalling Ca²⁺-binding in aqueous media

• Aurélien Ducrot,
• Arnaud Tron,
• Robin Bofinger,
• Ingrid Sanz Beguer,
• Jean-Luc Pozzo and
• Nathan D. McClenaghan

Beilstein J. Org. Chem. 2019, 15, 2801–2811, doi:10.3762/bjoc.15.273

• argon over sodium benzophenone ketyl. CH2Cl2 was distilled over CaH2 under argon. Mass spectrometry was performed at the CESAMO analytical center (University of Bordeaux, France) on a QStar Elite mass spectrometer (Applied Biosystems). The instrument is equipped with an electrospray ion (ESI) source and

• spectra were recorded in the positive mode. High-resolution mass spectrometry (HRMS) measurements were performed with an ESI source on a Q-TOF mass spectrometer with an accuracy tolerance of 2 ppm (Fédération de Recherche CBM/ICOA (FR2708) platform). The electrospray needle was maintained at 5000 V and

Nanangenines: drimane sesquiterpenoids as the dominant metabolite cohort of a novel Australian fungus, Aspergillus nanangensis

• Heather J. Lacey,
• Cameron L. M. Gilchrist,
• Andrew Crombie,
• John A. Kalaitzis,
• Daniel Vuong,
• Peter J. Rutledge,
• Peter Turner,
• John I. Pitt,
• Ernest Lacey,
• Yit-Heng Chooi and
• Andrew M. Piggott

Beilstein J. Org. Chem. 2019, 15, 2631–2643, doi:10.3762/bjoc.15.256

• -resolution positive electrospray ionisation mass spectrometry (HRESI(+)MS) analysis of nanangenine A (1) revealed an adduct ion ([M + Na]+ m/z 305.1363) indicative of a molecular formula C15H22O5 requiring five double bond equivalents (DBE). No distinguishing absorption maxima were observed in the UV–vis

• series HPLC equipped with an Agilent 6130 Infinity series single quadrupole mass detector in both positive and negative ion modes. High-resolution electrospray ionisation mass spectra (HRESIMS) were obtained on a Bruker Apex Qe 7T Fourier Transform Ion Cyclotron Resonance mass spectrometer equipped with

AgNTf₂-catalyzed formal [3 + 2] cycloaddition of ynamides with unprotected isoxazol-5-amines: efficient access to functionalized 5-amino-1H-pyrrole-3-carboxamide derivatives

• Ziping Cao,
• Jiekun Zhu,
• Li Liu,
• Yuanling Pang,
• Laijin Tian,
• Xuejun Sun and
• Xin Meng

Beilstein J. Org. Chem. 2019, 15, 2623–2630, doi:10.3762/bjoc.15.255

• ), d (doublet), dd (doublet of doublets), t (triplet), q (quartet), and m (multiplet). All melting points are uncorrected and determined on an X-4 digital microscopic melting point apparatus. HRMS were measured using electrospray ionization (ESI). Ynamide compounds 4a–q were prepared according to the

Anion-driven encapsulation of cationic guests inside pyridine[4]arene dimers

• Anniina Kiesilä,
• Jani O. Moilanen,
• Anneli Kruve,
• Christoph A. Schalley,
• Perdita Barran and
• Elina Kalenius

Beilstein J. Org. Chem. 2019, 15, 2486–2492, doi:10.3762/bjoc.15.241

• + formed complexes with 1 and 12, neither using electrospray ionization (ESI) in the positive nor the negative mode. Pr4N+ is certainly too large to fit inside the dimeric capsule, whereas the other non-complexing cations are protic and – as rather strong hydrogen-bond donors – may interfere with

Azologization and repurposing of a hetero-stilbene-based kinase inhibitor: towards the design of photoswitchable sirtuin inhibitors

• Christoph W. Grathwol,
• Nathalie Wössner,
• Sören Swyter,
• Adam C. Smith,
• Enrico Tapavicza,
• Robert K. Hofstetter,
• Anja Bodtke,
• Manfred Jung and
• Andreas Link

Beilstein J. Org. Chem. 2019, 15, 2170–2183, doi:10.3762/bjoc.15.214

• with a Torus DIOL (Waters) or Phenomenex CSP (Lux Amylose-2, i-Amylose-3, i-Cellulose-5), a degasser (DGU-20A5R), a communications module (CBM-20A), and two back pressure regulators BPR A and B (SFC-30A). UV and MS spectra were recorded via photodiode array detection (SPD-M20A) and electrospray

α-Photooxygenation of chiral aldehydes with singlet oxygen

• Dominika J. Walaszek,
• Magdalena Jawiczuk,
• Jakub Durka,
• Olga Drapała and
• Dorota Gryko

Beilstein J. Org. Chem. 2019, 15, 2076–2084, doi:10.3762/bjoc.15.205

• chemical shifts (δ) and coupling constants (J) are expressed in ppm and Hertz, respectively. High-resolution mass spectrometry (HRMS) data were obtained at the Synapt G2-S HDMS mass spectrometer equipped with an electrospray ion source and q-TOF type mass analyzer. Specific rotation was measured on a JASCO

Synthesis of a [6]rotaxane with singly threaded γ-cyclodextrins as a single stereoisomer

• Jason Yin Hei Man and
• Ho Yu Au-Yeung

Beilstein J. Org. Chem. 2019, 15, 1829–1837, doi:10.3762/bjoc.15.177

• HKU Foundation Postgraduate Fellowship. We acknowledge UGC funding administered by The University of Hong Kong for support of the Electrospray Ionization Quadrupole Time-of-Flight Mass Spectrometry Facilities under support for Interdisciplinary Research in Chemical Science.

Complexation of 2,6-helic[6]arene and its derivatives with 1,1′-dimethyl-4,4′-bipyridinium salts and protonated 4,4'-bipyridinium salts: an acid–base controllable complexation

• Jing Li,
• Qiang Shi,
• Ying Han and
• Chuan-Feng Chen

Beilstein J. Org. Chem. 2019, 15, 1795–1804, doi:10.3762/bjoc.15.173

• -polar solvent, acetone hampers or competes the intermolecular non-covalent interactions between the hosts and the guests, and thus resulted in a decrease of the host–guest complexation. ESIMS studies of the formation of host–guest complexes The electrospray ionization (ESI) mass spectra also confirmed