- Staudinger ligation towards cyclodextrin dimers in aqueous/organic media. Synthesis, conformations and guest-encapsulation ability
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β-Cyclodextrin (β-CD) dimers have been prepared using the bioorthogonal Staudinger ligation for the first time. In addition to a known linker, methyl 2-(diphenylphosphanyl)terephthalate, a doubly active linker was specifically developed that enabled conne
- Manouilidou, Malamatenia D.,Lazarou, Yannis G.,Mavridis, Irene M.,Yannakopoulou, Konstantina
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- Reactivity and synthetic utility of 1-(arenesulfonyloxy) benziodoxolones
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The reactivity and synthetic use of 1-(arenesulfonyloxy)benziodoxolones were studied. In the presence of iodine, 1-(arenesulfonyloxy)benziodoxolones iodinated various aromatics to give iodoarenes in moderate to good yields. In particular, 1-(p-chlorobenzenesulfonyloxy)benziodoxolone showed the best reactivity. Using a halide salt such as lithium bromide or lithium chloride instead of iodine, the corresponding aryl bromides and chlorides were also obtained in good yields. In the absence of aromatics, 1- (arenesulfonyloxy)benziodoxolones gave rise to desulfonyloxyiodination reactions to give the corresponding aryl iodides via electrophilic ipso substitution on the aromatic rings. Furthermore, the l-(p- toluenesulfonyloxy)benziodoxolone/iodine system iodotosyloxylated alkynes in good yields. These reactions proceeded via the formation of arenesulfonyl hypoiodites.
- Muraki, Takahito,Togo, Hideo,Yokoyama, Masataka
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- Triggering the dynamics of a carbazole-: P -[phenylene-diethynyl]-xylene rotor through a mechanically induced phase transition
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A new rotor exhibits rich solvatomorphism behavior with eight X-ray structures obtained. A heterogeneous solid obtained by mechanical stress exhibited a dominant isotropic 2H line shape at high temperatures. The motion occurs only in the amorph
- Aguilar-Granda, Andrés,Colin-Molina, Abraham,Jellen, Marcus J.,Nú?ez-Pineda, Alejandra,Cifuentes-Quintal, M. Eduardo,Toscano, Rubén Alfredo,Merino, Gabriel,Rodríguez-Molina, Braulio
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- Synthetic use of 1-(p-toluenesulfonyloxy)-1,2-benziodoxol-3(1H)-one: Iodination of aromatic rings
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Treatment of various aromatic compounds with 1-(p-toluenesulfonyloxy)-1,2-benziodoxol-3(1H)-one 1A and iodine gave the corresponding iodinated compounds in good yields. Similarly, chlorination and bromination proceeded effectively. As compared with other trivalent iodine compounds, the iodinane 1A showed the best reactivity as a halogenation reagent.
- Muraki, Takahito,Togo, Hideo,Yokoyama, Masataka
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- New cruciform structures: Toward coordination induced single molecule switches
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(Chemical Equation Presented) New cruciform structures 1-4 were synthesized to investigate a new single molecule switching mechanism arising from the interplay between the molecule and the electrode surface. These molecular cruxes consist of two rod-type
- Grunder, Sergio,Huber, Roman,Horhoiu, Viviana,Gonzalez, Maria Teresa,Schoenenberger, Christian,Calame, Michel,Mayor, Marcel
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- R4NHal/NOHSO4: A Usable System for Halogenation of Isoxazoles, Pyrazoles, and beyond
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A new convenient and versatile halogenating system (R4NHal/NOHSO4), giving straightforward and general access to halogenated 3,5-diaryl- and alkylarylisoxazoles, pyrazoles and electron-rich benzenes from the corresponding scaffolds, is suggested. The method provides excellent regioselectivity, scalability to the gram scale, and a broad scope for both aromatics and halogens. A three-step, one-pot reaction protocol was developed, and a series of 3,5-diaryl-4-haloisoxazoles has been efficiently synthesized from 1,2-diarylcyclopropanes under suggested nitrosating-halogenating conditions.
- Bondarenko, Oksana B.,Karetnikov, Georgy L.,Komarov, Arseniy I.,Pavlov, Aleksandr I.,Nikolaeva, Svetlana N.
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supporting information
p. 322 - 332
(2021/01/14)
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- Exploring the nitro group reduction in low-solubility oligo-phenylenevinylene systems: Rapid synthesis of amino derivatives
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A small series of amino oligo-phenylenevinylenes (OPVs) were successfully synthesized from their nitro-analogs in a rapid, simple, and highly efficient fashion employing a sodium sulfide/pyridine system as a reducing agent. In this research, classic and sustainable reduction methodologies including NH4HCO2/Zn and a choline chloride/tin (II) chloride deep eutectic solvent (DES) were also evaluated, showing degradation products, incomplete reactivity, and product isolation difficulties in all cases. The straightforward Na2S/pyridine synthetic protocol proved to maintain the E-E stereochemistry of the OPV backbone that has been previously assembled by the Mizoroki–Heck cross-coupling reaction. Also, the optoelectronic properties were determined and discussed, considering the amino group insertion in these conjugated systems as a contribution for future construction of novel materials with applications in supramolecular electronics, light harvesting, and photocatalysis.
- Acelas, Mauricio,Sierra, Andrés Felipe,Sierra, César A.
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supporting information
p. 1335 - 1352
(2020/03/04)
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- Metal-Free, Oxidant-Free, and Controllable Graphene Oxide Catalyzed Direct Iodination of Arenes and Ketones
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A direct, metal-free, and oxidant-free method for the graphene oxide (GO)-catalyzed iodination of arenes and ketones with iodine in a neutral medium was explored. This iodination protocol was performed by using a simple technique to avoid the use of external metal catalysts and oxidants and harsh acidic/basic reaction conditions. In addition, by this method the degree of iodination could be controlled, and the reaction was scalable and compatible with air. This strategy opens a new field for GO-catalyzed chemistry and provides an avenue for the convenient direct iodination of arenes and ketones.
- Zhang, Jingyu,Li, Shiguang,Deng, Guo-Jun,Gong, Hang
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p. 376 - 380
(2017/12/07)
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- Substituent Effects That Control Conjugated Oligomer Conformation through Non-covalent Interactions
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Although understanding the conformations and arrangements of conjugated materials as solids is key to their prospective applications, predictive power over these structural factors remains elusive. In this work, substituent effects tune non-covalent interactions between side-chain fluorinated benzyl esters and main-chain terminal arenes, in turn controlling the conformations and interchromophore aggregation of three-ring phenylene-ethynylenes (PEs). Cofacial fluoroarene-arene (ArF-ArH) interactions cause twisting in the PE backbone, interrupting intramolecular conjugation as well as blocking chromophore aggregation, both of which prevent the typically observed bathochromic shift observed upon transitioning PEs from solution to solid. This work highlights two structural factors that determine whether the ArF-ArH interactions, and the resulting twisted, unaggregated chromophores, occur in these solids: (i) the electron-releasing characteristic of substituents on ArH, with more electron-releasing character favoring ArF-ArH interactions, and (ii) the fluorination pattern of the ArF ring, with 2,3,4,5,6-pentafluorophenyl favoring ArF-ArH interactions over 2,4,6-trifluorophenyl. These trends indicate that considerations of electrostatic complementarity, whether through a polar-π or substituent-substituent mechanism, can serve as an effective design principle in controlling the interaction strengths, and therefore the optoelectronic properties, of these molecules as solids.
- Sharber, Seth A.,Baral, Rom Nath,Frausto, Fanny,Haas, Terry E.,Müller, Peter,Thomas, Samuel W.
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supporting information
p. 5164 - 5174
(2017/05/04)
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- Oligo p-Phenylenevinylene Derivatives as Electron Transfer Matrices for UV-MALDI
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Phenylenevinylene oligomers (PVs) have outstanding photophysical characteristics for applications in the growing field of organic electronics. Yet, PVs are also versatile molecules, the optical and physicochemical properties of which can be tuned by manipulation of their structure. We report the synthesis, photophysical, and MS characterization of eight PV derivatives with potential value as electron transfer (ET) matrices for UV-MALDI. UV-vis analysis show the presence of strong characteristic absorption bands in the UV region and molar absorptivities at 355 nm similar or higher than those of traditional proton (CHCA) and ET (DCTB) MALDI matrices. Most of the PVs exhibit non-radiative quantum yields (φ) above 0.5, indicating favorable thermal decay. Ionization potential values (IP) for PVs, calculated by the Electron Propagator Theory (EPT), range from 6.88 to 7.96 eV, making these oligomers good candidates as matrices for ET ionization. LDI analysis of PVs shows only the presence of radical cations (M+.) in positive ion mode and absence of clusters, adducts, or protonated species; in addition, M+. threshold energies for PVs are lower than for DCTB. We also tested the performance of four selected PVs as ET MALDI matrices for analytes ranging from porphyrins and phthalocyanines to polyaromatic compounds. Two of the four PVs show S/N enhancement of 1961% to 304% in comparison to LDI, and laser energy thresholds from 0.17 μJ to 0.47 μJ compared to 0.58 μJ for DCTB. The use of PV matrices also results in lower LODs (low fmol range) whereas LDI LODs range from pmol to nmol. [Figure not available: see fulltext.].
- Castellanos-García, Laura J.,Agudelo, Brian Castro,Rosales, Hernando F.,Cely, Melissa,Ochoa-Puentes, Christian,Blanco-Tirado, Cristian,Sierra, Cesar A.,Combariza, Marianny Y.
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p. 2548 - 2560
(2017/12/12)
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- Topology-guided design and syntheses of highly stable mesoporous porphyrinic zirconium metal-organic frameworks with high surface area
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Through a topology-guided strategy, a series of Zr6-containing isoreticular porphyrinic metal-organic frameworks (MOFs), PCN-228, PCN-229, and PCN-230, with ftw-a topology were synthesized using the extended porphyrinic linkers. The bulky porphyrin ring ligand effectively prevents the network interpenetration which often appears in MOFs with increased linker length. The pore apertures of the structures range from 2.5 to 3.8 nm, and PCN-229 demonstrates the highest porosity and BET surface area among the previously reported Zr-MOFs. Additionally, by changing the relative direction of the terminal phenyl rings, this series replaces a Zr8 cluster with a smaller Zr6 cluster in a topologically identical framework. The high connectivity of the Zr6 cluster yields frameworks with enhanced stability despite high porosity and ultralarge linker. As a representative example, PCN-230, constructed with the most extended porphyrinic linker, shows excellent stability in aqueous solutions with pH values ranging from 0 to 12 and demonstrates one of the highest pH tolerances among all porphyrinic MOFs. This work not only presents a successful example of rational design of MOFs with desired topology, but also provides a strategy for construction of stable mesoporous MOFs.
- Liu, Tian-Fu,Feng, Dawei,Chen, Ying-Pin,Zou, Lanfang,Bosch, Mathieu,Yuan, Shuai,Wei, Zhangwen,Fordham, Stephen,Wang, Kecheng,Zhou, Hong-Cai
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supporting information
p. 413 - 419
(2015/01/30)
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- Preparation of phosphonoterephthalic acids via palladium-catalyzed coupling of aromatic iodoesters
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The current article reports in detail the preparation of two phosphonoterephthalic acids: 2-phosphonoterephthalic acid (1) and 2,5-diphosphonoterephthalic acid (2). Efficient, scalable syntheses have been developed for both compounds based on Pd-catalyzed
- Ivan, Nathaniel,Benin, Vladimir,Morgan, Alexander B.
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supporting information
p. 1831 - 1836
(2013/05/22)
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- Structure, theoretical studies, and coupling reactions of some new cyclic boronic esters
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The present report describes the X-ray structural and theoretical studies of some new pinacolboronate esters, and it also outlines the use of the target structures in Suzuki coupling reactions to produce new aromatic or heteroaromatic esters and amides. X
- Kuttler, Andrew,Durganala, Sravanthi,Fratini, Albert,Morgan, Alexander B.,Benin, Vladimir
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p. 361 - 371
(2013/09/23)
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- Synthesis and characterization of a low-bandgap poly(arylene ethynylene) having donor-acceptor type chromophores in the side chain
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A low-bandgap poly(arylene ethynylene) (PAE) having donor-acceptor type chromophores in the side chain was synthesized. A π-conjugated PAE precursor having electron-rich dioctylanilino-substituted alkynes in the side chain was polymerized through Sonogashira cross-coupling reaction between functional monomers M-I with terminal acetylenes and M-II with diiodide, using tetrakis(tripheneylphosphine)palladium and copper iodide catalysts in a mixed solvent of triethylamine and tetrahydrofuran (THF) at 50°C. The electronically rich N,N-dioctylamino groups in M-I activated the alkynes in the side chains of M-I, thus making the selective reaction of sidechain alkynes with TCNE possible in the post-functionalization step. The selective reaction of TCNE (tetracyanoethylene) with activated dioctylanilino substituted alkynes in the side chains of precursor polymer afforded the target poly(arylene ethynylene). This unique polymer shows enhanced thermal stability and exhibits strong intramolecular charge-transfer interactions, resulting in a very low bandgap of poly(arylene ethynylene).
- Huang, Wenyi,Chen, Hongyan
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p. 2032 - 2037
(2013/04/24)
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- Potassium 4-iodylbenzenesulfonate: Preparation, structure, and application as a reagent for oxidative iodination of arenes
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A new hypervalent iodine(V) compound, potassium 4-iodylbenzenesulfonate, was prepared by the oxidation of 4-iodobenzensulfonic acid with Oxone in water. This potassium salt can be further converted into 4-iodylbenzenesulfonic acid by treatment with the acidic form of Amberlyst 15 in water. A single-crystal X-ray structure of potassium 4-iodylbenzenesulfonate revealed the presence of polymeric chains in the solid state due to a combination of numerous intra- and intermolecular interactions. Potassium 4-iodylbenzenesulfonate will likely find many practical applications as a thermally stable and water-soluble hypervalent iodine-based oxidant, particularly useful as a reagent for oxidative iodination of aromatic substrates. This reagent can be effectively recovered from the reaction mixture (92 % recovery) by treatment of the aqueous layer with Oxone at 60°C for 2 h, followed by filtration of the precipitate. A new hypervalent iodine(V) compound, potassium 4-iodylbenzenesulfonate, was prepared by oxidation of 4-iodobenzenesulfonic acid with Oxone in water. This new reagent promises many practical applications as a thermally stable, water-soluble and recyclable hypervalent iodine oxidant, particularly useful for oxidative iodination of aromatic substrates.
- Yusubov, Mekhman S.,Yusubova, Roza Y.,Nemykin, Victor N.,Maskaev, Andrey V.,Geraskina, Margarita R.,Kirschning, Andreas,Zhdankin, Viktor V.
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p. 5935 - 5942,8
(2020/09/02)
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- Synthesis and flame retardant testing of new boronated and phosphonated aromatic compounds
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The present report describes the preparation and use of some dimethyl terephthalate derivatives in transition metal-catalyzed coupling reactions to produce new reactive flame retardants. Dimethyl iodoterephthalate and dimethyl 2,5-diiodoterephthalate were
- Benin, Vladimir,Durganala, Sravanthi,Morgan, Alexander B.
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scheme or table
p. 1180 - 1190
(2012/03/27)
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- Design principle of conjugated polyelectrolytes to make them water-soluble and highly emissive
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The correlation between the molecular design of a conjugated polyelectrolyte (CPE) and its aggregated structure and the emissive properties in water is systematically investigated by means of UV-vis spectrometry, fluorescence spectroscopy, and scanning/tr
- Lee, Kangwon,Kim, Hyong-Jun,Kim, Jinsang
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scheme or table
p. 1076 - 1086
(2012/07/30)
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- Synthesis of electron deficient acene derivatives via a bidirectional iterative elongation reaction
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Previously, we developed an iterative elongation methodology to synthesize acene esters, nitriles, and imides. The strategy uses the concept of bidirectional synthesis, and we can now make a series of electron deficient anthracene, tetracene, and pentacen
- Lin, Yi-Chun,Lin, Chih-Hsiu,Chen, Chan-Yu,Sun, Shih-Sheng,Pal, Bikash
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supporting information; experimental part
p. 4507 - 4517
(2011/07/08)
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- Novel cruciform structures as model compounds for coordination induced single molecule switches
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We have synthesized various molecular cruciforms consisting of two different crossing π-systems and comprising crosswise arranged thiol- and pyridine-anchor groups. With these model compounds we strive towards the investigation of a new switching concept based on the potential dependent coordination of pyridines to gold electrodes in an electrochemical set-up. Integration of these cruciform molecules between both electrodes of a mechanically controlled break junction in a liquid environment gave insight into their single molecule transport properties. These studies allowed individual transport characteristics to be assigned to the bar subunits of the cruciforms but also revealed the remaining experimental challenges to realize the suggested switching concept. Schweizerische Chemische Gesellschaft.
- Grunder, Sergio,Huber, Roman,Wu, Songmei,Schoenenberger, Christian,Calame, Michel,Mayor, Marcel
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scheme or table
p. 140 - 144
(2011/08/04)
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- Desulfonyloxyiodination of arenesulfonic acids with mCPBA and molecular iodine
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Treatment of p-alkylbenzenesulfonic acids with mCPBA and molecular iodine gave p-alkyliodobenzenes in good to moderate yields via electrophilic ipso-substitution by the iodonium species (I+) formed. This desulfonyloxyiodination was promoted by the addition of a catalytic amount of iodoarenes, such as o-iodobenzoic acid. The same treatment of dimethylbenzenesulfonic acids and trimethylbenzenesulfonic acids with mCPBA and molecular iodine proceeded smoothly both in the absence and in the presence of o-iodobenzoic acid to provide the corresponding monoiodo-dimethylbenzene and diiodo-dimethylbenzene, and diiodo-trimethylbenzene and triiodo- trimethylbenzene, in good to moderate yields, respectively. On the other hand, the same desulfonyloxyiodination of benzenesulfonic acid and p-chlorobenzenesulfonic acid with mCPBA and molecular iodine proceeded only in the presence of o-iodobenzoic acid to generate iodobenzene and p-chloroiodobenzene, respectively, in moderate yields.
- Suzuki, Yuhsuke,Ishiwata, Yoshihide,Moriyama, Katsuhiko,Togo, Hideo
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experimental part
p. 5950 - 5953
(2010/11/21)
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- METHOD OF PRODUCING IODIZING AGENT, AND METHOD OF PRODUCING AROMATIC IODINE COMPOUND
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A method of the present invention, for producing an iodizing agent, includes the step of electrolyzing iodine molecules in a solution by using an acid as a supporting electrolyte. This realizes (i) a method of producing an iodine cation suitable for use as an iodizing agent that does not require a sophisticated separation operation after iodizing reaction is completed, and (ii) an electrolyte used in the method. Further, a method of the present invention, for producing an aromatic iodine compound, includes the step of causing an iodizing agent, and an aromatic compound whose nucleus has one or more substituent groups and two or more hydrogen atoms, to react with each other under the presence of a certain ether compound. This realizes such a method of producing an aromatic iodine compound that position selectivity in iodizing reaction of an aromatic compound is improved.
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Page/Page column 11
(2010/05/13)
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- "Clickable" metal-organic framework
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We demonstrated the metal-organic framework bearing the azide group in the organic linkers and in situ click reactions with some small alkynes. The XRPD patterns indicated that the click reaction proceeded without any decomposition of the original MOF net
- Goto, Yuta,Sato, Hiroki,Shinkai, Seiji,Sada, Kazuki
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supporting information; experimental part
p. 14354 - 14355
(2009/02/08)
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- Selective and effective iodination of alkyl-substituted benzenes with elemental iodine activated by Selectfluor F-TEDA-BF4
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Selective direct introduction of an iodine atom into alkyl-substituted benzene derivatives was effectively achieved by reaction of target molecules with elemental iodine in the presence of 1-chloromethyl-4-fluoro- 1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (Selectfluor F-TEDA-BF4). The number of iodine atoms introduced could be modulated by the molar ratio between substrate, iodine and F-TEDA-BF4.
- Stavber, Stojan,Kralj, Petra,Zupan, Marko
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p. 598 - 600
(2007/10/03)
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- 2,4,6,8-tetraiodo-2,4,6,8-tetraazabicyclo[3.3.0]octane-3,7-dione as a mild and convenient reagent for iodination of aromatic compounds
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2,4,6,8-Tetraiodo-2,4,6,8-tetraazabicyclo[3.3.0]octane-3,7-dione (tetraiodoglycoluril) is a convenient reagent for preparative iodination of benzene, alkylbenzenes, polycyclic hydrocarbons, aromatic amines, and phenol ethers in organic solvents under mild conditions.
- Chaikovski,Filimonov,Yagovkin,Ogorodnikov
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p. 2411 - 2415
(2007/10/03)
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- Improved, Acid-catalyzed Iodinating Procedures for Activated Aromatics with (Diacetoxyiodo)benzene as the Oxidant
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Improved procedures for the oxidative, acid-catalyzed iodination of benzene, iodobenzene and several activated aromatics are presented to give mono-, di-, or triiodinated products in 40-82 percent yields. The reactions proceeded at room temperature in the anhydrous systems: arene or hetarene/diiodine/(diacetoxyiodo)benzene (2)/glacial acetic acid/acetic anhydride, acidified with catalytic amounts of concd. (98 percent) H2SO4. Within at most 15 minutes the iodine coloration faded; the following workups are explained. A similar treatment with dibromine gave tribromomesitylene (65 percent), dibromodurene (62 percent), and 2,7-dibromofluoren-9-one (73 percent). A review on the aromatic halogenation reactions with organic trivalent iodine reagents as the oxidants is presented below.
- Kryska, Anna,Skulski, Lech
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p. 2501 - 2517
(2007/10/03)
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- Fluorescent chemosensors based on energy migration in conjugated polymers: The molecular wire approach to increased sensitivity
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We demonstrate herein how conjugated polymers (molecular wires) can be used to interconnect (wire in series) receptors to produce fluorescent chemosensory systems with sensitivity enhancements over single receptor analogues. The enhancement mechanism in t
- Zhou, Qin,Swager, Timothy M.
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p. 12593 - 12602
(2007/10/03)
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- Photochemical Synthesis of Carbon-14 Labelled Dibenzanthracene
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Carrier-free dibenzanthracene (DBA,12*) has been prepared for the first time using methyl iodide as the source of the label.The key step in this radiosynthesis consisted of the regiospecific photocyclization of 2',5'-divinyl-1,1':4',1''-terphenyl 10* to 5,6,12,13-tetrahydro-DBA 11* followed by dehydrogenation to 12* with DDQ (2,3-dichloro-5,6-dicyano-1,4-benzoquinone).Divinylterphenyl 10* was obtained from 2',5'-bis(bromomethyl)-1,1':4',1''-terphenyl 3 via the diformyl derivative 9 and its Wittig olefination with the triphenylphosphonium salt of14CH3I.Thus 12* was synthesized with a radiochemical purity exceeding 99percent.The chemical yield amounted to 58percent from 9 in the case of 12* with a specific activity of 391 MBq mmol-1 and to 12percent in the case of carrier-free 12* with a specific activity of 4.14 GBq mmol-1.Wide applicability of this radiosynthetic approach to the preparation of many other carbon-14 labelled polycyclic aromatic hydrocarbons can be envisaged.
- Platt, Karl L.,Setiabudi, Frans
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p. 2005 - 2010
(2007/10/02)
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- Halogenation Using Quaternary Ammonium Polyhalides. XIV. Aromatic Bromination and Iodination of Arenes by Use of Benzyltrimethylammonium Polyhalides-Zinc Chloride System
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The reaction of arenes with benzyltrimethylammonium tribromide or benzyltrimethylammonium dichloroiodate in acetic acid in the presence of ZnCl2 at room temperature or at 70 deg C gave brome- or iodo-substituted arenes in good yield, respectively.
- Kajigaeshi, Shoji,Kakinami, Takaaki,Moriwaki, Masayuki,Tanaka, Toshio,Fujisaki, Shizuo,Okamoto, Tsuyoshi
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p. 439 - 443
(2007/10/02)
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- A SIMPLE METHOD FOR THE IODINATION OF AROMATIC COMPOUNDS
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The iodine - (trifluoroacetoxyiodo)benzene system is effective for the iodination of aromatic compounds, alkylbenzenes, various polynuclear aromatic hydrocarbons, halogenobenzenes, and some heterocyclic compounds.Trifluoroacetyl hypoiodite, which is a source of electrophilic iodine, is probably formed initially.Trifluoroacetyl hypoiodite can be generated in situ from (diacetoxyiodo)benzene and trifluoroacetic acid.
- Merkushev, E. B.,Yudina, N. D.
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p. 2320 - 2322
(2007/10/02)
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