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Mechanochemistry
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Mechanochemistry

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Organic Chemistry".

Deadline for manuscript submissions: closed (20 June 2016) | Viewed by 54238

Special Issue Editors

Prof. Dr. Carsten Bolm

E-Mail Website
Guest Editor
Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, D-52074 Aachen, Germany
Interests: enantioselective catalysis; asymmetric synthesis; bioactive compounds; mechanochemistry; biomass conversion; sulfur and fluorine chemistry
Prof. Dr. Koichi Komatsu

E-Mail Website
Guest Editor
Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011, Japan
Interests: mechanochemistry; fullerene chemistry; synthesis and properties of carbocations; synthesis and properties of novel pi-conjugated hydrocarbons

Special Issue Information

Dear Colleagues,

Mechanochemistry has its roots in chemistry and mechanical engineering. Since a long time it has found applications in the fields of inorganic chemistry, polymer science, etc. More recently, mechanochemistry has also blossomed in organic chemistry being recognized as "clean" and "green" method allowing to perform reactions in the absence of solvents which are often harmful to the environment. Thus overall, “mechanochemistry” has increasingly become important in present-day society. Thus, works concerning any aspect of “mechanochemistry” are welcome in this Special Issue.

Prof. Dr. Koichi Komatsu
Prof. Dr. Carsten Bolm
Guest Editors

Manuscript Submission Information

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Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Molecules is an international peer-reviewed open access semimonthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2700 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.


 

Keywords

  • solid-solid reactions
  • solvent-free reactions
  • mechanical engineering
  • technique of mechanochemistry
  • mechanisms in mechanochemistry

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Published Papers (6 papers)

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Research

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2940 KiB  
Article
Mechanochemical Lignin-Mediated Strecker Reaction
by Saumya Dabral, Mathias Turberg, Andrea Wanninger, Carsten Bolm and José G. Hernández
Molecules 2017, 22(1), 146; https://doi.org/10.3390/molecules22010146 - 17 Jan 2017
Cited by 25 | Viewed by 7999
Abstract
A mechanochemical Strecker reaction involving a wide range of aldehydes (aromatic, heteroaromatic and aliphatic), amines, and KCN afforded a library of α-aminonitriles upon mechanical activation. This multicomponent process was efficiently activated by lignocellulosic biomass as additives. Particularly, commercially available Kraft lignin was found [...] Read more.
A mechanochemical Strecker reaction involving a wide range of aldehydes (aromatic, heteroaromatic and aliphatic), amines, and KCN afforded a library of α-aminonitriles upon mechanical activation. This multicomponent process was efficiently activated by lignocellulosic biomass as additives. Particularly, commercially available Kraft lignin was found to be the best activator for the addition of cyanide to the in situ formed imines. A comparative study of the 31P-NMR (Nuclear Magnetic Resonance) along with IR (Infrared) data analysis for the Kraft lignin and methylated Kraft lignin samples ascertained the importance of the free hydroxyl groups in the activation of the mechanochemical reaction. The solvent-free mechanochemical Strecker reaction was then coupled with a lactamization process leading to the formation of the N-benzylphthalimide (5a) and the isoindolinone derivative 6a. Full article
(This article belongs to the Special Issue Mechanochemistry)
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1177 KiB  
Article
Ball Milling Assisted Solvent and Catalyst Free Synthesis of Benzimidazoles and Their Derivatives
by Taghreed H. EL-Sayed, Asmaa Aboelnaga and Mohamed Hagar
Molecules 2016, 21(9), 1111; https://doi.org/10.3390/molecules21091111 - 24 Aug 2016
Cited by 26 | Viewed by 7888
Abstract
Benzoic acid and o-phenylenediamine efficiently reacted under the green solvent-free Ball Milling method. Several reaction parameters were investigated such as rotation frequency; milling balls weight and milling time. The optimum reaction condition was milling with 56.6 g weight of balls at 20 [...] Read more.
Benzoic acid and o-phenylenediamine efficiently reacted under the green solvent-free Ball Milling method. Several reaction parameters were investigated such as rotation frequency; milling balls weight and milling time. The optimum reaction condition was milling with 56.6 g weight of balls at 20 Hz frequency for one hour milling time. The study was extended for synthesis of a series of benzimidazol-2-one or benzimidazol-2-thione using different aldehydes; carboxylic acids; urea; thiourea or ammonium thiocyanate with o-phenylenediamine. Moreover; the alkylation of benzimidazolone or benzimidazolthione using ethyl chloroacetate was also studied. Full article
(This article belongs to the Special Issue Mechanochemistry)
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5383 KiB  
Article
Selective Extraction of Flavonoids from Sophora flavescens Ait. by Mechanochemistry
by Qihong Zhang, Jingbo Yu, Yingyao Wang and Weike Su
Molecules 2016, 21(8), 989; https://doi.org/10.3390/molecules21080989 - 29 Jul 2016
Cited by 16 | Viewed by 6390
Abstract
Flavonoids from Sophora flavescens were selectively extracted by mechanochemical-promoted extraction technology (MPET) after using response surface methodology to determine the optimal extraction parameters. The highest yield of 35.17 mg/g was achieved by grinding the roots with Na2CO3 (15%) at 440 [...] Read more.
Flavonoids from Sophora flavescens were selectively extracted by mechanochemical-promoted extraction technology (MPET) after using response surface methodology to determine the optimal extraction parameters. The highest yield of 35.17 mg/g was achieved by grinding the roots with Na2CO3 (15%) at 440 rpm/min for 17.0 min and water was used as the sole solvent with a ratio of solvent to solid material of 25 mL/g. Flavonoids prepared by MPET demonstrated relatively higher antioxidant activities in subsequent DPPH and hydroxyl radical scavenging assays. Main constituents in the extracts, including kurarinol, kushenol I/N and kurarinone, were characterized by HPLC-MS/MS, indicating good selective extraction by MPET. Physicochemical property changes of powder during mechanochemical milling were identified by scanning electron microscopy, X-ray powder diffraction, and UV-Vis diffuse-reflectance spectroscopy. Compared with traditional extraction methods, MPET possesses notable advantages of higher selectivity, lower extraction temperature, shorter extraction time, and organic solvent free properties. Full article
(This article belongs to the Special Issue Mechanochemistry)
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4271 KiB  
Article
In Situ Investigation of a Self-Accelerated Cocrystal Formation by Grinding Pyrazinamide with Oxalic Acid
by Hannes Kulla, Sebastian Greiser, Sigrid Benemann, Klaus Rademann and Franziska Emmerling
Molecules 2016, 21(7), 917; https://doi.org/10.3390/molecules21070917 - 14 Jul 2016
Cited by 37 | Viewed by 8071
Abstract
A new cocrystal of pyrazinamide with oxalic acid was prepared mechanochemically and characterized by PXRD, Raman spectroscopy, solid-state NMR spectroscopy, DTA-TG, and SEM. Based on powder X-ray diffraction data the structure was solved. The formation pathway of the reaction was studied in situ [...] Read more.
A new cocrystal of pyrazinamide with oxalic acid was prepared mechanochemically and characterized by PXRD, Raman spectroscopy, solid-state NMR spectroscopy, DTA-TG, and SEM. Based on powder X-ray diffraction data the structure was solved. The formation pathway of the reaction was studied in situ using combined synchrotron PXRD and Raman spectroscopy. Using oxalic acid dihydrate the initially neat grinding turned into a rapid self-accelerated liquid-assisted grinding process by the release of crystallization water. Under these conditions, the cocrystal was formed directly within two minutes. Full article
(This article belongs to the Special Issue Mechanochemistry)
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4862 KiB  
Article
Selective Extraction of Gardenia Yellow and Geniposide from Gardenia jasminoides by Mechanochemistry
by Wenhao Xu, Jingbo Yu, Wen Feng and Weike Su
Molecules 2016, 21(5), 540; https://doi.org/10.3390/molecules21050540 - 28 Apr 2016
Cited by 25 | Viewed by 8560
Abstract
A novel method for the selective extraction of gardenia yellow and geniposide from Gardenia Jasminoides, based on a mechanochemical method is described. Without the need of complex separation techniques, gardenia yellow compliant with the national standard could be extracted in a simple [...] Read more.
A novel method for the selective extraction of gardenia yellow and geniposide from Gardenia Jasminoides, based on a mechanochemical method is described. Without the need of complex separation techniques, gardenia yellow compliant with the national standard could be extracted in a simple fashion. The optimal ball-milling conditions determined were as follows: 30% g/g. active carbon milling at 200 rpm in a planetary mill for 5 min. The extraction conditions of the milled mixtures were as follows: the milled mixtures were extracted with water (liquid-solid ratio 10:1) at 20 °C for 5 min with yields 85% of total geniposide, followed by extraction with 80% ethanol solution (liquid-solid ratio 5:1) and 1% g/g. Tween 20 at 75 °C for 5 min to yield 1.45% ± 0.108% g/g of gardenia yellow. The mechanism of this selective extraction was demonstrated to follow a microstructure change of activated carbon, which occurred during milling and lead to alteration of the corresponding desorption capacities. Compared with traditional extraction methods, this novel extraction technique greatly simplifies the separation process, and proves to be advantageous in terms of low organic solvent consumption, easy operation, rapid process and high efficiency. Full article
(This article belongs to the Special Issue Mechanochemistry)
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Review

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7726 KiB  
Review
Advances in Solid-State Transformations of Coordination Bonds: From the Ball Mill to the Aging Chamber
by Cristina Mottillo and Tomislav Friščić
Molecules 2017, 22(1), 144; https://doi.org/10.3390/molecules22010144 - 17 Jan 2017
Cited by 122 | Viewed by 13751
Abstract
Controlling the formation of coordination bonds is pivotal to the development of a plethora of functional metal-organic materials, ranging from coordination polymers, metal-organic frameworks (MOFs) to metallodrugs. The interest in and commercialization of such materials has created a need for more efficient, environmentally-friendly [...] Read more.
Controlling the formation of coordination bonds is pivotal to the development of a plethora of functional metal-organic materials, ranging from coordination polymers, metal-organic frameworks (MOFs) to metallodrugs. The interest in and commercialization of such materials has created a need for more efficient, environmentally-friendly routes for making coordination bonds. Solid-state coordination chemistry is a versatile greener alternative to conventional synthesis, offering quantitative yields, enhanced stoichiometric and topological selectivity, access to a wider range of precursors, as well as to molecules and materials not readily accessible in solution or solvothermally. With a focus on mechanochemical, thermochemical and “accelerated aging” approaches to coordination polymers, including pharmaceutically-relevant materials and microporous MOFs, this review highlights the recent advances in solid-state coordination chemistry and techniques for understanding the underlying reaction mechanisms. Full article
(This article belongs to the Special Issue Mechanochemistry)
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