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TABLE OF CONTENTS

Volume 21 Issue 8 , Pages 613 - 718 (August 2007)


Contents

Contents (p i-v)

Published Online: Jun 28 2007 9:51AM
DOI: 10.1002/aoc.1302

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Bioorganometallic Chemistry

On the medicinal chemistry of ferrocene (p 613-625)
Mohammad F. R. Fouda, Mokhles M. Abd-Elzaher, Rafeek A. Abdelsamaia, Ammar A. Labib
Published Online: Apr 11 2007 6:32AM
DOI: 10.1002/aoc.1202

 

The use of ferrocene in bioorganometal-lic chemistry has been growing rapidly, and several promising applications have been developed since ferrocene is a stable compound, nontoxic and has good redox properties. This review will focus on ferrocenyl compounds which have been biologically evaluated against certain diseases. This area has attracted many researchers due to the promising results of some ferrocene compounds in the medicinal applications.

 

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Synthesis, characterization and in vitro cytotoxicity of homobimetallic complexes of palladium(II) with 2-thiouracil ligands. Crystal structure of [Pd2(TU)(PPh3)3Cl2] (p 626-632)
Farkhanda Shaheen, Amin Badashah, Marcel Gielen, L. Marchio, Dick de Vos, M.aleemhosa
Published Online: May 4 2007 4:30AM
DOI: 10.1002/aoc.1227

 

Square planar metallic and homonuclear bimetallic complexes of Pd(II) with 2-thiouracil (HTU) and organophosphines have been synthesized and characterized by FT-IR and multinuclear 1H, 13C, 31P NMR spectroscopy. The thiouracil ligand TU acts as bidentate, is bound through the thioxo moiety and the endo amino group and forms a bridge between a PdCl(R3P) and a PdCl(R3P)2 moiety [R3P = Ph3P, (o-tolyl)3P, ClPh2P] in the homonuclear bimetallic complexes. The square planar geometry around Pd(II) has been confirmed for these complexes by a single-crystal X-ray diffraction study of compound 1, [Pd2(TU)(PPh3)3Cl2]. These compounds were also screened against human tumor cell lines and showed promising in vitro cytotoxicity.

 

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Synthesis, characterization and in vitro cytotoxicity of palladium(II) complexes with mixed ligands. X-ray diffraction study of C31H36ClNPPdS2 (p 633-640)
Farkhanda Shaheen, Amin Badshah, Marcel Gielen, Christine Gieck, Dick de Vos
Published Online: May 4 2007 4:34AM
DOI: 10.1002/aoc.1245

 

Pd(II) complexes with organophosphines and dithiocarbamates derivatives of -amino acids were synthesized by reacting N,N-dicyclohexyldithiocarbamate (DCHDTC, compounds 1-3) and N-methylcyclohexyldithiocarbamate (MCHDTC, compounds 4-6) with (R3P)2PdCl2 (R = Ph, o-tolyl, Ph2Cl) in a 1:1 molar ratio. The complexes were characterized by elemental analyses, FT-IR, multinuclear (1H, 13C and 31P) NMR and single X-ray crystallography showing that the dithiocarbamate acts as a bidentate ligand and binds to Pd(II) via two sulfur atoms resulting in a square planar geometry around Pd(II). The cytotoxicity of compounds 2, 3 and 4 was determined in vitro against six human tumour cell lines, MCF7, EVSA-T, WIDR, IGROV, M19 MEL, A498 and H226. The compounds 3 and 4 showed a moderate to low cytotoxicity whereas compound 2 exhibited a very low cytotoxicity. The results of antifungal assays showed that compounds 1-6 possess antifungal activity against Fusarium moniliformes, Fusarium saolani, Mucor sp., Aspergillus niger and Aspergillus fumigatus. The anti-inflammatory screening results of 1-6 are quite similar to the one observed for the standard drug Declofenac at 10 mg/kg, which inhibited the oedema by 74% after 4 hours.

 

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Materials, Nanoscience and Catalysis

2-Iminopyridylpalladium dichloride as highly active catalyst for the Heck reaction (p 641-644)
Weixuan Chen, Chanjuan Xi,e Yang
Published Online: Apr 18 2007 11:24AM
DOI: 10.1002/aoc.1224

 

Seven different palladium (II) complexes containing pyridyl-imine ligands have been investigated as catalysts for the coupling between aryl bromide and olefin. The substituent on the benzene ring had significant influence on the catalytic properties. The catalyst 2 shows the highest reactivity of coupling reaction with aryl bromide in NMP with2CO3 at 140 °C.

 

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Biomimetic synthesis of gold nanoparticles and their aggregates using a polypeptide sequence (p 645-651)
Zheng Wang, Jinchun Chen, Peng Yang, Wantai Yang
Published Online: Apr 27 2007 6:06AM
DOI: 10.1002/aoc.1222

 

The polypeptide sequence MS14 (MHGK- TQATSGTIQS) was used to explore a new way of biomimetic preparation of gold nanoparticles and their aggregates. Extra reducing agent sodium citrate was introduced into the HAuCl4-MS14 system and uniformly dispersed nanoparticles under neutral condition were obtained.

 

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Synthesis of ultra-low-molecular-weight polyethylene wax using a bulky Ti(IV) aryloxide-alkyl aluminum catalytic system (p 652-660)
Prashant S. Umare, Ajaykumar J. Tiwari, Robin Antony, Gopal L. Tembe, Bhavna Trivedi
Published Online: May 4 2007 4:31AM
DOI: 10.1002/aoc.1233

 

Soluble complexes of titanium containing bulky phenolic ligands were synthesized by an alcohol exchange reaction between Ti(OPri)4 and the phenols. All these complexes were found to be active in polymerization of ethylene at high temperatures and pressures in combination with Et3Al2Cl3 as co-catalyst. The polyethylene so obtained display very low molecular weights, narrow dispersities and high crystallinity.

 

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The liquid crystalline properties of some ferrocene-containing Schiff bases (p 661-669)
Irina Cârlescu, Ana Maria Scutaru, Daniela Apreutesei, Valentina Alupei, Dan Scutaru
Published Online: May 15 2007 8:31AM
DOI: 10.1002/aoc.1242

 

A series of Shiff bases containing ferrocene, with liquid crystalline properties, have been synthesized and characterized. The size of the rigid core of the substituent on ferrocene was found to play an important role in determining the thermal properties of these compounds.

 

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Palladium chloride anchored on organic functionalized MCM-41 as a catalyst for the Heck reaction (p 670-675)
Guo-zhi Fan, Si-qing Cheng, Ming-fang Zhu, Xin-lei Gao
Published Online: May 25 2007 9:34AM
DOI: 10.1002/aoc.1244

 

Palladium chloride anchored on func- tionalized MCM-41 was synthesized. The heterogeneous catalyst exhibited high catalytic performance in the Heck reaction of iodobenzene with methyl acrylate, giving 92% yield of methyl cinnamate. The heterogeneous catalyst was recycled six times without significant loss of activity and palladium leaching.

 

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Main Group Metal Compounds

Ionic 1,2,5-oxonia- and zwitterionic 1,2,5-oxasilaboratole derivatives. Synthesis and molecular structures (p 676-681)
Bernd Wrackmeyer, Tomasupcik, Oleg L. Tok,hadija Shahid, Rhettempe
Published Online: Apr 11 2007 6:44AM
DOI: 10.1002/aoc.1223

 

Alkenes bearing a chloro(dimethyl)silyl and a diethylboryl group in cis-positions at the Cdbond;C bond together with a dimethylaminomethyl group in geminal position to the silyl group react with water or alcohols to give novel ammonium salts, 2,5-dihydro-1,2,5-oxoniaboratole derivatives.

 

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Three-step synthesis of arylpolyboronic acids from phenols via organotin compounds (p 682-687)
Pablo M. Fidelibus, Gustavo F. Silbestri, María T. Lockhart, Sandra D. Mandolesi, Alicia B. Chopa, Julio C. Podestá
Published Online: Apr 11 2007 6:50AM
DOI: 10.1002/aoc.1225

 

Phenols were converted into the aryla1225ga.eps diethyl phosphates (II). Reaction of II with sodium trimethylstannide in liquid ammonia leads to the corresponding aryl- and heteroarylpoly(trimethylstannyl) derivatives (III). Organotins III react with borane in THF to give arylpolyboronic acids IV in ca 80% yield. The valuable arylboronic acids are obtained pure and uncontaminated by organotin residues and by other organic and inorganic boron derivatives as well as free of organic halides.

 

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Aluminum(III) complexes containing O,O chelating ligand (p 688-693)
Libor Dostál, Roman Jambor, Ivana Císarcaronová, Jan Merna, Jaroslav Holeccaronek
Published Online: Apr 27 2007 6:09AM
DOI: 10.1002/aoc.1226

 

Reactions between 2,6-(MeOCH2)2C6H3OHa1226ga.eps (LH) and trimethylaluminum in various ratios were studied. The products of these reactions were characterized with the help of 1H, 13C NMR spectroscopy and X-ray diffraction. The PPO and -caprolactone polymerization activity of the L2AlMeB(C6F5)3 system is also discussed.

 

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Mono- and heterodi-nuclear complexes of aluminium: synthesis, characterization and antifungal activity (p 694-700)
Vaishali Vajpayee, Y. P. Singh, Durgesh Nandani, Amla Batra
Published Online: Apr 27 2007 6:11AM
DOI: 10.1002/aoc.1230

 

Some new type of mononuclear deriva- tives AlLLH(1a-1d) of aluminium have been synthesized by 1:2 molar ratio by the reaction of Al(OPri)3 and LH2 [XC(NYOH)CH(R)OH], X = CH3, Y = (CH2)2, R = CH3(L1H2); X = C6H5, Y = (CH2)2, R = CH3(L2H2); X = CH3, Y = (CH2)3, R = CH3(L3H2); X = C6H5, Y = (CH2)3, R = CH3(L4H2) in refluxing benzene. Reactions of AlLLH with hexamethyldisilazane in 2:1 molar ratio yield some new ligand bridged heterodinuclear derivatives AlLLSiMe3(2a-2d). All these newly synthesized derivatives have been characterized by elemental analysis and molecular weight measurements. Tentative structures have been proposed on the basis of IR and NMR spectra (1H, 13Cl, 27Al and 29Si) and FAB-mass studies. Schiff base ligand and their mono- and heterodi-nuclear derivatives with aluminium have been screened for their fungicidal activities. These compounds showed significant antifungal activity against Aspergillus niger and A. flavus.

 

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The antispermatogenic activity of some phenylbismuth(III) O,Oprime-dialkyldithiophosphates (p 701-710)
Pankaj. Sharma, H. Rehwani, R. S. Gupta, Y. P. Singh
Published Online: May 24 2007 11:37AM
DOI: 10.1002/aoc.1238

 

Ten dialkyldithiophosphate derivatives of phenylbismuth(III) of the type, Ph(3-n)Bi[S(S)P(OR)2]n [where n = 1; R = Me (1), Et(2), Pri (3), Prn (4) and Bun (5); n = 2; R = Me (6), Et (7), Pri (8), Prn (9) and Bun (10)] have been synthesized by the reactions of triphenyl-bismuth(III) with corresponding dialkyldithiophosphoric acids in 1:1 and 1:2 stoichiometric ratios, respectively, in stirred benzene solution. The newly synthesized brown colored compounds, 1-10 have been characterized by elemental analyses, molecular weight measurements, IR and NMR (1H, 13C and 31P) spectral studies. The ligand diethyldithiophosphoric acid, [(C2H5O)2P(S)SH] and its organobismuth(III) derivatives, compounds 2 and 7 were administered to adult male rats by oral gavage at the dose of 25 mg perg body weight per day, for 60 days, and their effects were evaluated and compared for changes in testicular morphology, circulatory concentrations of testosterone, FSH and LH, sperm dynamics, fertility index and testicular cell population dynamics.

 

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Application of N,N-bis(diphenylphosphino)aniline palladium(II) complexes as pre-catalysts in Heck coupling reactions (p 711-715)
Bahattin Gümgüm, Nermin Biricik, Feyyaz Durap, Ismail Özdemir, Nevin Gürbüz, Wee Han Ang, Paul J. Dyson
Published Online: Jun 7 2007 4:20AM
DOI: 10.1002/aoc.1253

 

Crystal structures of N,N-bis(diphenyl-a1253ga.eps phosphino)-2,3-dimethylaniline-Pd(II) and N,N-bis(diphenylphosphino)-2-ethyl- aniline-Pd(II) complexes have been determined and the catalytic influence of the complexes was investigated in Heck reactions.

 

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Book Reviews

Jens Hagen. Industrial catalysis: a practical approach. Wiley-VCH, 2006, 2nd edn, 525 pp; ISBN 978-3-527-31144-6 (hardcover) (p 716)
Philip C.H. Mitchell
Published Online: Jun 28 2007 9:51AM
DOI: 10.1002/aoc.1247

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Richard Dronskowski. Computational chemistry of solid-state materials: a guide for materials scientists, chemists, physicists and others. Wiley-VCH, 2005, 294 pp; ISBN 3-978-3-527-31410-2 (hardcover) (p 717)
David Willock
Published Online: Jun 28 2007 9:51AM
DOI: 10.1002/aoc.1257

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Errata

In vivo toxicological effects and spectral studies of organotin(IV) N-maleoylglycinates M. I.han, Musaaleem Baloch, Muhammad Ashfaq and G. J. Peters Applied Organometallic Chemistry 2005; 19: 132 (p 718)

Published Online: Apr 11 2007 7:03AM
DOI: 10.1002/aoc.1208

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