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Search for "neat" in Full Text gives 321 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.

The B & B approach: Ball-milling conjugation of dextran with phenylboronic acid (PBA)-functionalized BODIPY

  • Patrizia Andreozzi,
  • Lorenza Tamberi,
  • Elisamaria Tasca,
  • Gina Elena Giacomazzo,
  • Marta Martinez,
  • Mirko Severi,
  • Marco Marradi,
  • Stefano Cicchi,
  • Sergio Moya,
  • Giacomo Biagiotti and
  • Barbara Richichi

Beilstein J. Org. Chem. 2020, 16, 2272–2281, doi:10.3762/bjoc.16.188

Graphical Abstract
  • reactions, and even in nanomaterials preparation [1][2][3][4][5]. Indeed, solid-state mechanochemical methodologies are a viable alternative to traditional syntheses in solution [4] for the preparation of complex molecules, either under solvent-free conditions, named ‘neat grinding’, or in nearly solvent
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Published 11 Sep 2020

Access to highly substituted oxazoles by the reaction of α-azidochalcone with potassium thiocyanate

  • Mysore Bhyrappa Harisha,
  • Pandi Dhanalakshmi,
  • Rajendran Suresh,
  • Raju Ranjith Kumar and
  • Shanmugam Muthusubramanian

Beilstein J. Org. Chem. 2020, 16, 2108–2118, doi:10.3762/bjoc.16.178

Graphical Abstract
  • points reported in the work are uncorrected. Unless stated otherwise, solvents and chemicals were obtained from commercial sources and used without further purification. Infrared spectra were recorded on a Perkin Elmer instrument with neat sample and only major peaks are reported in cm−1. The 1H and 13C
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Published 31 Aug 2020

Selective preparation of tetrasubstituted fluoroalkenes by fluorine-directed oxetane ring-opening reactions

  • Clément Q. Fontenelle,
  • Thibault Thierry,
  • Romain Laporte,
  • Emmanuel Pfund and
  • Thierry Lequeux

Beilstein J. Org. Chem. 2020, 16, 1936–1946, doi:10.3762/bjoc.16.160

Graphical Abstract
  • equiv) in dichloromethane. The reaction was slow and required heating (50–65 °C) for 26 h to reach a 75% conversion and afforded a mixture of E/Z-1a in 60% yield. However, a low E/Z selectivity (40:60) was observed (Table 1, entry 1). When using neat benzylic alcohol, completion was achieved after 20 h
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Published 07 Aug 2020

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

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Published 26 Jun 2020

The McKenna reaction – avoiding side reactions in phosphonate deprotection

  • Katarzyna Justyna,
  • Joanna Małolepsza,
  • Damian Kusy,
  • Waldemar Maniukiewicz and
  • Katarzyna M. Błażewska

Beilstein J. Org. Chem. 2020, 16, 1436–1446, doi:10.3762/bjoc.16.119

Graphical Abstract
  • , being especially affected by the type of substituents in the vicinity of the phosphonic group [1]. Usually the reaction is carried out for 1–3 days [26][27], in a solution of DCM or acetonitrile (ACN), although it can also be performed in neat BTMS. As far as the reaction temperature is concerned it can
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Published 23 Jun 2020

Oxime radicals: generation, properties and application in organic synthesis

  • Igor B. Krylov,
  • Stanislav A. Paveliev,
  • Alexander S. Budnikov and
  • Alexander O. Terent’ev

Beilstein J. Org. Chem. 2020, 16, 1234–1276, doi:10.3762/bjoc.16.107

Graphical Abstract
  • oxime 1g (Scheme 5). Oxime radical 16 is a pale blue crystalline compound that is stable at room temperature [35][62], whereas liquid neat di-tert-butyliminoxyl radical (8) decomposed within a week [59]. The di(1-adamantyl)iminoxyl radical (16) was characterized by IR, UV–vis, EPR, and NMR spectroscopy
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Published 05 Jun 2020

The charge-assisted hydrogen-bonded organic framework (CAHOF) self-assembled from the conjugated acid of tetrakis(4-aminophenyl)methane and 2,6-naphthalenedisulfonate as a new class of recyclable Brønsted acid catalysts

  • Svetlana A. Kuznetsova,
  • Alexander S. Gak,
  • Yulia V. Nelyubina,
  • Vladimir A. Larionov,
  • Han Li,
  • Michael North,
  • Vladimir P. Zhereb,
  • Alexander F. Smol'yakov,
  • Artem O. Dmitrienko,
  • Michael G. Medvedev,
  • Igor S. Gerasimov,
  • Ashot S. Saghyan and
  • Yuri N. Belokon

Beilstein J. Org. Chem. 2020, 16, 1124–1134, doi:10.3762/bjoc.16.99

Graphical Abstract
  • ). Both the pH of the medium (specific acid catalysis) and general acid catalysis by the ammonium groups of F-1 were potentially important for the ring opening reactions. The ring openings were conducted in three different media: neat methanol, a mixture of methanol and dichloromethane, and a mixture of
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Published 26 May 2020

Aryl-substituted acridanes as hosts for TADF-based OLEDs

  • Naveen Masimukku,
  • Dalius Gudeika,
  • Oleksandr Bezvikonnyi,
  • Ihor Syvorotka,
  • Rasa Keruckiene,
  • Dmytro Volyniuk and
  • Juozas V. Grazulevicius

Beilstein J. Org. Chem. 2020, 16, 989–1000, doi:10.3762/bjoc.16.88

Graphical Abstract
  • ) spectra of neat films, and dilute THF and toluene solutions of the studied derivatives are presented in Figure 3a. The derivatives 3, 4, and 6 exhibited intense acridan-related lowest energy bands (LEB) of absorption at ≈340 nm, affected by the type of substituents. The LEB of the solutions and films of 5
  • stabilizes the twist conformers stimulating the formation of intermolecular CT states. Consequently, in the PL spectra of neat films of the derivatives the emission band assigned to CT is more prominent. The PL quantum yields of neat films of compound 3, 4, 5, and 6 were found to be 0.03, 0.08, 0.32 and 0.08
  • [29]. DSC curves of compounds 4 and 5. Absorption and PL spectra (λex = 330 nm) of compounds 3–6. a) Absorption spectra as neat films, dilute THF and toluene solutions. b) PL and phosphorescence spectra in dilute THF solutions at 77 K. a) Cyclic voltammogram of derivative 3 in dichloromethane (a three
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Published 13 May 2020

Preparation of 2-phospholene oxides by the isomerization of 3-phospholene oxides

  • Péter Bagi,
  • Réka Herbay,
  • Nikolett Péczka,
  • Zoltán Mucsi,
  • István Timári and
  • György Keglevich

Beilstein J. Org. Chem. 2020, 16, 818–832, doi:10.3762/bjoc.16.75

Graphical Abstract
  • trifluoroacetic acid, a mixture containing the corresponding 2- and 3-phospholene oxides (4a and 1a) in a ratio of 11:89 was obtained. However, when phospholene oxide 1a was heated in neat methanesulfonic acid at 160 °C for 24 h, 4a and 1a in a ratio of 97:3 were obtained, but the yield of the mixture was 57% due
  • toluene, DMF, or DMSO. However, the maximal content of phenyl-2-phospholene oxide 4a in the crude product was only 4%. In contrast, when neat 3-phospholene oxide 1a was heated to 200 °C without any solvent, the ratio of the 2- and 3-phospholene oxide 4a and 1a increased to 71:29 in the crude product after
  • °C in neat, and the progression of the reactions was followed by gas chromatography for two days using biphenyl as internal standard. According to repeated experiments, the errors in measured relative concentrations were below 5%. The concentration curves undoubtedly refer to an equilibrium reaction
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Published 22 Apr 2020

Towards triptycene functionalization and triptycene-linked porphyrin arrays

  • Gemma M. Locke,
  • Keith J. Flanagan and
  • Mathias O. Senge

Beilstein J. Org. Chem. 2020, 16, 763–777, doi:10.3762/bjoc.16.70

Graphical Abstract
  • Hz); IR (neat)/cm−1) ν̃: 2921 (w), 2851 (w), 1560 (m), 1535 (m), 1412 (m), 1386 (s), 1257 (s), 1154 (m), 1103 (s), 1070 (s), 982 (m), 912 (m), 750 (s), 739 (m), 638 (m), 580 (w); UV–vis (CHCl3): λmax [nm] (log ε): 367 (5.57), 506 (5.97); HRMS–MALDI (m/z): [M]+ calcd for C54H32N4F4B2, 834.2749; found
  • , 126.2, 123.2, 121.6, 96.8, 88.9, 54.639.2, 35.8, 31.9, 30.4, 22.7, 14.0; UV–vis (CHCl3) λmax [nm] (log ε): 434 (6.06), 564 (4.28), 610 (4.20); IR (neat)/cm−1) ν̃: 2921 (m), 2851 (m), 1451 (m), 1305 (m), 1211 (m), 1072 (m), 1008 (s), 939 (m), 787 (s), 750 (s), 708 (s), 639 (s); HRMS–MALDI (m/z): [M
  • , 94.4, 89.9, 54.4, 53.9, 39.1, 35.8, 32.1, 30.5, 29.8, 22.9, 19.0, 14.3, 11.7 ppm; IR (neat)/cm−1) ν̃: 2921 (m), 2851 (m), 1451 (m), 1305 (m), 1211 (m), 1072 (m), 1008 (s), 939 (m), 787 (s), 750 (s), 708 (s), 639 (s); UV–vis (CHCl3) λmax [nm] (log ε): 430 (5.84), 563 (4.30), 608 (4.35); HRMS–MALDI (m/z
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Published 17 Apr 2020

Aerobic synthesis of N-sulfonylamidines mediated by N-heterocyclic carbene copper(I) catalysts

  • Faïma Lazreg,
  • Marie Vasseur,
  • Alexandra M. Z. Slawin and
  • Catherine S. J. Cazin

Beilstein J. Org. Chem. 2020, 16, 482–491, doi:10.3762/bjoc.16.43

Graphical Abstract
  • for C50H66BCuF4N6: C, 66.62; H, 7.38; N, 9.32; found: C, 66.55; H, 7.46; N, 9.47. General catalytic procedure. A vial was charged with [Cu(Triaz)2]BF4 (4.5 mg, 1 mol %), the alkyne (0.5 mmol), the azide (0.6 mmol) and the amine (0.6 mmol). The reaction was stirred neat for the appropriate amount of
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Published 24 Mar 2020

Combination of multicomponent KA2 and Pauson–Khand reactions: short synthesis of spirocyclic pyrrolocyclopentenones

  • Riccardo Innocenti,
  • Elena Lenci,
  • Gloria Menchi and
  • Andrea Trabocchi

Beilstein J. Org. Chem. 2020, 16, 200–211, doi:10.3762/bjoc.16.23

Graphical Abstract
  • following the reported method [48] employing copper catalysis, and tested on our starting material upon variation of copper salts, solvents and temperature, resulting in the neat reaction under CuI catalysis being optimal when carried out for 2 h at 100 °C under microwave irradiation (see Supporting
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Published 12 Feb 2020

Microwave-assisted synthesis of 2-substituted 4,5,6,7-tetrahydro-1,3-thiazepines from 4-aminobutanol

  • María C. Mollo,
  • Natalia B. Kilimciler,
  • Juan A. Bisceglia and
  • Liliana R. Orelli

Beilstein J. Org. Chem. 2020, 16, 32–38, doi:10.3762/bjoc.16.5

Graphical Abstract
  • necessary precursors were prepared by the sequence depicted in Table 1. Regarding the cyclodehydration reaction, in the same experimental conditions than before (neat PPSE, 1–8 min, 90 °C), thioamidoalcohols 3i–k afforded the corresponding tetrahydro-1,3-thiazepines 4i–k in good to high yields as the only
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Published 06 Jan 2020

Extension of the 5-alkynyluridine side chain via C–C-bond formation in modified organometallic nucleosides using the Nicholas reaction

  • Renata Kaczmarek,
  • Dariusz Korczyński,
  • James R. Green and
  • Roman Dembinski

Beilstein J. Org. Chem. 2020, 16, 1–8, doi:10.3762/bjoc.16.1

Graphical Abstract
  • , 149.4, 137.2, 115.6, 114.6, 103.6, 85.7, 82.4, 81.8, 74.0, 63.7, 37.9, 35.6, 33.8, 20.9, 20.6; IR (neat, ATR) 3197, 3077, 2967, 2089, 2049, 2017, 1747, 1714, 1691, 1587 cm−1; ESI+–MS (m/z): [M]+ calcd for C25H22Co2N2O13, 698.9684; found, 698.9689. Hexacarbonyl dicobalt 3',5'-di-O-acetyl-2'-deoxy-5-[3
  • ); 13C NMR (125 MHz, CDCl3) δ 199.4, 170.3, 160.3, 160.1, 158.9, 149.6, 136.2, 115.1, 108.7, 104.1, 90.0, 85.7, 82.3, 81.1, 74.1, 63.8, 55.3, 54.7, 37.7, 26.5, 20.9, 20.6; IR (neat, ATR) 3200, 2997, 2962, 2088, 2048, 2018, 1746, 1711, 1664, 1598 cm−1; ESI+–MS (m/z): [M]+ calcd for C31H28Co2N2O16
  • , 81.8, 74.0, 63.7, 40.2, 37.8, 28.9, 20.9, 20.6; IR (neat, ATR) 3208, 2956, 2926, 2089, 2050, 2018, 1746, 1715, 1688, 1597 cm−1; ESI+–MS (m/z): [M + Na]+ calcd for C30H25Co2N2NaO14, 776.9789; found, 776.9788. Hexacarbonyl dicobalt 2',3',5'-tri-O-acetyl-5-(hex-5-en-1-yn-1-yl)uridine (7a). To a solution
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Published 02 Jan 2020

SnCl4-catalyzed solvent-free acetolysis of 2,7-anhydrosialic acid derivatives

  • Kesatebrhan Haile Asressu and
  • Cheng-Chung Wang

Beilstein J. Org. Chem. 2019, 15, 2990–2999, doi:10.3762/bjoc.15.295

Graphical Abstract
  • as catalyst under neat conditions, which provided the expected β-ring-opened product 12 in a moderate yield (Table 1, entry 5). This acetolysis reaction resulted in regioselective acetylation of positions O-7 and O-2 in line with the principles of green chemistry. It is known that anomeric acetates
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Published 23 Dec 2019

A new approach to silicon rhodamines by Suzuki–Miyaura coupling – scope and limitations

  • Thines Kanagasundaram,
  • Antje Timmermann,
  • Carsten S. Kramer and
  • Klaus Kopka

Beilstein J. Org. Chem. 2019, 15, 2569–2576, doi:10.3762/bjoc.15.250

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  • starting material 12 could be significantly reduced when acetonitrile was exchanged with dichloromethane in the triflation reaction to provide triflate 21 neat and more reliable. Screening of different boron species and catalysts showed that, like in the syntheses of O, S, Se, and Te-rhodamines, boroxines
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Published 29 Oct 2019

α,ß-Didehydrosuberoylanilide hydroxamic acid (DDSAHA) as precursor and possible analogue of the anticancer drug SAHA

  • Shital K. Chattopadhyay,
  • Subhankar Ghosh,
  • Sarita Sarkar and
  • Kakali Bhadra

Beilstein J. Org. Chem. 2019, 15, 2524–2533, doi:10.3762/bjoc.15.245

Graphical Abstract
  • viscous liquid [45]. IR (neat): 3267, 3076, 1666, 1579 cm−1; 1HNMR (400 MHz, CDCl3) δ 8.33 (brs, 1H), 7.56 (d, J = 8 Hz, 2H), 7.29 (t, J = 7.6 Hz, 2H), 7.10 (t, J = 7.6 Hz, 1H), 5.84–5.74 (m, 1H), 5.03–4.95 (m, 2H), 2.36 (t, J = 7.6 Hz, 2H), 2.06 (q, J = 6.8 Hz, 2H), 1.72 (quin, J = 7.2 Hz, 2H), 1.44
  • cool to room temperature and then concentrated in vacuo. The residual mass was purified by column chromatography on silica gel (CHCl3/MeOH 98:2) to provide the coupled product 10a (101 mg, 77%) as colourless solid. Mp 148–150 °C; IR (neat): 3296, 3211, 2926, 2858, 1663, 1639 cm−1; 1H NMR (400 MHz, DMSO
  • Celite, the filter cake was washed with methanol (5 mL) and the combined filtrate was concentrated in vacuo. The residue was purified by column chromatography on silica gel (CHCl3/MeOH 9:1) to provide SAHA (34 mg, 91%) as colorless solid. Mp 158–159 °C; IR (neat): 3267, 2927, 2854, 1667, 1645 cm–1; 1H
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Published 24 Oct 2019

An overview of the cycloaddition chemistry of fulvenes and emerging applications

  • Ellen Swan,
  • Kirsten Platts and
  • Anton Blencowe

Beilstein J. Org. Chem. 2019, 15, 2113–2132, doi:10.3762/bjoc.15.209

Graphical Abstract
  • particularly thermally unstable, with dimerization occurring at temperatures higher than −75 °C [4]. The dimerization of triafulvene derivatives is hypothesised to occur via a [4 + 4] cycloaddition pathway (Scheme 7) [4]. Whilst the dimers are also unstable (rapid decomposition when neat), they can be observed
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Published 06 Sep 2019

Reactions of 2-carbonyl- and 2-hydroxy(or methoxy)alkyl-substituted benzimidazoles with arenes in the superacid CF3SO3H. NMR and DFT studies of dicationic electrophilic species

  • Dmitry S. Ryabukhin,
  • Alexey N. Turdakov,
  • Natalia S. Soldatova,
  • Mikhail O. Kompanets,
  • Alexander Yu. Ivanov,
  • Irina A. Boyarskaya and
  • Aleksander V. Vasilyev

Beilstein J. Org. Chem. 2019, 15, 1962–1973, doi:10.3762/bjoc.15.191

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  • of 1 and give rise to the corresponding 2-diarylmethylbenzimidazoles 9a–l. The best results were obtained in neat TfOH, which gave high yields of reaction products (54–86%) at room temperature after 2–3 h. Other acids were not so efficient. Thus, reactions under the action of sulfuric acid H2SO4 or
  • . Then, we studied reactions of 2-hydroxyalkylbenzimidazoles 3a–c, 4, 7, and 8. It was found that these reactions needed extremely harsh reaction conditions, heating in neat TfOH at 140 °C in glass high pressure tubes (Table 4, Scheme 2). Only at this high temperature the formation of Friedel–Crafts
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Published 19 Aug 2019

Vicinal difunctionalization of alkenes by four-component radical cascade reaction of xanthogenates, alkenes, CO, and sulfonyl oxime ethers

  • Shuhei Sumino,
  • Takahide Fukuyama,
  • Mika Sasano,
  • Ilhyong Ryu,
  • Antoine Jacquet,
  • Frédéric Robert and
  • Yannick Landais

Beilstein J. Org. Chem. 2019, 15, 1822–1828, doi:10.3762/bjoc.15.176

Graphical Abstract
  • was then filtered and concentrated in vacuo to give a residue, which was subjected to silica gel column chromatography using hexane/EtOAc 10:1 as eluent, affording 5a (52.9 mg, 0.15 mmol, 38%). Ethyl (E)-4-(2-((benzyloxy)imino)acetyl)decanoate (5a): IR (neat, ZnSe) νmax (cm−1): 3065, 2955, 1732, 1584
  • , 31.6, 29.2, 27.1, 26.4, 22.6, 14.2, 14.1; EIMS m/z (relative intensity): 316 (4), 227 (8), 199 (2), 91 (100); HRMS–EI (m/z): [M − C2H5O]+ calcd for C19H26NO3, 316.1913; found, 316.1916. Phenyl (E)-4-(2-((benzyloxy)imino)acetyl)decanoate (5b): IR (neat, ZnSe) νmax (cm−1): 2954, 2928, 1760, 1685, 1196
  • -((benzyloxy)imino)-4-cyclohexyl-5-oxohexanoate (5c): IR (neat, ZnSe) νmax (cm−1): 3065, 2978, 1681, 1497, 1370, 1251, 1210; 1H NMR (CDCl3, 500 MHz) δ 7,48 (s, 1H), 7.38–7.33 (m, 5H), 5.25 (s, 2H), 4.12–4.06 (m, 2H), 3.27–3.23 (m, 1H), 2.22–2.17 (m, 1H), 2,13–2.06 (m, 1H), 1.96–1.92 (m, 1H), 1.86–1.85 (m, 1H
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Published 31 Jul 2019

N-(1-Phenylethyl)aziridine-2-carboxylate esters in the synthesis of biologically relevant compounds

  • Iwona E. Głowacka,
  • Aleksandra Trocha,
  • Andrzej E. Wróblewski and
  • Dorota G. Piotrowska

Beilstein J. Org. Chem. 2019, 15, 1722–1757, doi:10.3762/bjoc.15.168

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Published 23 Jul 2019

Recent advances on the transition-metal-catalyzed synthesis of imidazopyridines: an updated coverage

  • Gagandeep Kour Reen,
  • Ashok Kumar and
  • Pratibha Sharma

Beilstein J. Org. Chem. 2019, 15, 1612–1704, doi:10.3762/bjoc.15.165

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Published 19 Jul 2019

Formation of an unexpected 3,3-diphenyl-3H-indazole through a facile intramolecular [2 + 3] cycloaddition of the diazo intermediate

  • Andrew T. King,
  • Hugh G. Hiscocks,
  • Lidia Matesic,
  • Mohan Bhadbhade,
  • Roger Bishop and
  • Alison T. Ung

Beilstein J. Org. Chem. 2019, 15, 1347–1354, doi:10.3762/bjoc.15.134

Graphical Abstract
  • product was crystallised from dichloromethane to give a brown crystalline solid (0.064 g, 0.137 mmol, 27%); mp 183–184 °C; IR (neat) vmax/cm−1: 3057, 3025, 2959, 2926, 2650, 2322, 2112, 1943, 1591, 1490, 1470, 1445, 1349, 1263, 1205, 1127, 1023, 843, 748, 607; 1H NMR (500 MHz, CDCl3) δ 7.28–7.31 (m, H-Ar
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Published 19 Jun 2019

Efficient resolution of racemic crown-shaped cyclotriveratrylene derivatives and isolation and characterization of the intermediate saddle isomer

  • Sven Götz,
  • Andreas Schneider and
  • Arne Lützen

Beilstein J. Org. Chem. 2019, 15, 1339–1346, doi:10.3762/bjoc.15.133

Graphical Abstract
  • corresponds to the saddle conformer and is marked with 1-S. a) 1H NMR spectrum of the neat crown isomers of (rac)-1 in CD3OD (400 MHz, 298 K); b) 1H NMR spectrum in CD3OD (400 MHz, 298 K) of a sample of (rac)-1 after heating it to 200 °C in DMSO and quenching the solution by pouring it into an ice water
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Published 18 Jun 2019

Understanding the unexpected effect of frequency on the kinetics of a covalent reaction under ball-milling conditions

  • Ana M. Belenguer,
  • Adam A. L. Michalchuk,
  • Giulio I. Lampronti and
  • Jeremy K. M. Sanders

Beilstein J. Org. Chem. 2019, 15, 1226–1235, doi:10.3762/bjoc.15.120

Graphical Abstract
  • less expensive than traditional solution-based methods, because they require little or no solvent. Moreover, mechanochemical syntheses often give quantitative yields of products [2][3][4]. Manual or mechanical grinding can be performed “neat”, i.e., in the absence of solvent (neat grinding, NG
  • Information File 2), which we selected here to fit the experimental curve for 15 Hz ball-mill neat grinding. If a model is built on Scheme 2, with k1, k1' k2, Figure 2A is generated. Remarkably, despite the simplifying assumptions used in this model, the general features of the experimental curve are well
  • by its ability to facilitate mass transport. Having ascertained that the model of Equation 4 well describes the non-linear kinetics observed for neat grinding, it is worth considering this model with respect to LAG kinetics. While the non-linearity is not so evident under LAG conditions, the
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Published 05 Jun 2019
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