POLISH JOURNAL OF CHEMISTRY
Volume 74 Number 2 February 2000
Pages 163-290


CONTENTS

INORGANIC CHEMISTRY

163

The Tb–Re–B System: Phase Equilibria and Crystal Structures

- Mykhalenko S.I. and Kuz’ma Yu.B.

173

Synthesis, Characterization and Magnetic Analysis of Bromanilato-Bridged Binuclear Iron(III) Complexes

- Li Y.T., Yan C.W. and Zeng X.C.

181

Synthesis of New Co(III) Hetero-Ligand Complexes with Imidazole and 1-Methylimidazole and Their 1H, 13C and 59Co NMR Spectra

- Danilczuk E., Grzelakowska A. and Michalska M.

191

The Synthesis, Spectroscopic Characterization, Crystal and Molecular Structure
of [ReBr3(NO)(dppe)]0.60[ReBr4(dppe)]0.40

- Dzięgielewski J.O., Machura B., Małecki J., Bartczak T.J. and Czurak W.

199

Synthesis and Characterization of Thiocyanato-Bridged Heteropolynuclear Chromium(III)–Copper(II) Complexes

- Dobrzańska L., Wrzeszcz G., Grodzicki A. and Rozpłoch F.

ORGANIC CHEMISTRY

207

Furo[2,3-b]pyrrole Derivatives. Syntheses and Reactions in the Furan and Pyrrole Ring

 - Sleziak R., Krutosikova; A., Cyrański M.K. and Krygowski T.M.

219

Fragments of a Proline-Rich Polypeptide Settled on a Hexapeptide Carcass Constructed of Glycine and L-Lysine Residues. Synthesis and Biological Properties

- Wirkus-Romanowska I., Miecznikowska H., Zabłocka A., Rybka K., Fortuna W., Mię;dzybrodzki R., Szymaniec S., Janusz M., Lisowski J. and Kupryszewski G.

227

Simple Synthesis of 2-Thioglycosyl Derivatives of Pyridine N-Oxide

- Pastuch G. and Szeja W.

PHYSICAL CHEMISTRY

231

Iodide Ion-Selective PVC Membrane Electrode Based on a Recently Synthesized Salen–Mn(II) Complex

- Shamsipur M., Sadeghi S., Naeimi H. and Sharghi H.

239

Thermodynamics of Substituted Pyrazolone. VI. Potentiometric and Conductometric Studies of Complexes of Some Transition Metals with 4-(4-Acetophenyl)hydrazono-3-methyl-1-phenyl-2-pyrazolin-5-one

- El-Bindary A.A., El-Sonbati A.Z. and Kera H.M.

245

Ab Initio Calculations of the Pairing of Four Canonical DNA Bases with Three Thymine Derivatives Generated by Hydroxyl Radical in Anaerobic Conditions

- Cysewski P.

257

Gas-Liquid Chromatographic Interactions for Twelve Benzene-Derived Chemical Functions on Twelve Polar Stationary Phases

- Santiuste J.M.

CRYSTAL AND MOLECULAR STRUCTURE

265

The Crystal, Molecular and Electronic Structure of [ReBr2(NO)(CO)(PPh3)2]×NO Complex

- Bartczak T.J., Czurak W., Dzięgielewski J.O., Machura B., Kusz J. and Warczewski J.

COMMUNICATIONS

275

Synthesis and Structure of [NH2(C2H5)2]4[0200_VP_EQN_0.GIFO42(H2O)]×2H2O

- Zeng Q.X., Xu J.Q.,Yang G.Y., Song Y.J., Pak Y.S., Xing Y.H., Wang R.Z., Li D.M., Xing Y., Lin Y.H. and Jia H.Q.

281

A New Lupane-Type Triterpenoid from Taraxacum officinale

- Kisiel W., Barszcz B. and Szneler E.

285

Synthesis and Crystal Structure of Tetrakis(trifluoroacetato) Bis(acetone) Dirhodium(II)

  Zhao Q.H., Bu W.M., Liao D.Z., Jiang Z.H. and Yan S.P.


163-171

The Tb–Re–B System: Phase Equilibria and Crystal Structures

by S.I. Mykhalenko and Yu.B. Kuz’ma

Ivan Franko State University of Lviv, Kyryla and Mefodiya str. 6, 290005, Lviv, Ukraine

(Received April 26th, 1999; revised manuscript July 26th, 1999)

The phase diagram at 1270 K of the Tb–Re–B system is constructed by X-ray analysis. The existence of the earlier known compounds is confirmed: Tb3ReB7 (Er3CrB7 structure type), TbReB4 (YCrB4 structure type, refined lattice parameters a = 5.9776(4), b = 11.5640(9), c = 3.6058(3) Å) and Tb2ReB6 (Y2ReB6 structure type, refined lattice parameters a = 9.206(4), b = 11.560(4), c = 3.669(1) Å). New ternary compounds are found and their crystal structures are determined: Tb8Re13-xB12 (DRON-3M powder diffractometer, R3m space group, Pr8Re13-xB12, structure type, a = 10.6233(6), c = 14.318(1) Å, Nhkl = 286, R = 0.095) and TbeRe4B4 (a single crystal method, the tetragonal incommensurate structure, a = 10.624(9), c = 38.29(9) Å).


173-180

Synthesis, Characterization and Magnetic Analysis of Bromanilato-Bridged Binuclear Iron(III) Complexes

by Y.-T. Li1, C.-W. Yan2 and X.-C. Zeng1

1Department of Chemistry, Sichuan University, Chengdu, Sichuan, 610064 , P. R. China
2Department of Biology, Qufu Normal University, Qufu, Shandong, 273165, P. R. China

(Received September 22nd, 1999)

Five new bromanilato-bridged binuclear iron(III) complexes have been synthesized and characterized, namely [Fe2(BA)L4](ClO4)4, where BA represents the dianion of bromanilic acid and L denotes 2,2¢-bipyridine (bpy); 1,10-phenanthroline (phen), 5-chloro1,10-phenanthroline (Cl-phen); 5-bromo-1,10-phenanthroline (Br-phen) or 5-nitro-1,10-phenanthroline (NO2-phen). Based on elemental analyses, molar conductivity, magnetic moment of room-temperature measurements, IR and electronic spectra studies, these complexes are proposed to have extended BA-bridged structures consisting of two iron(III) ions, each in a distorted octahedral environment. The complexes [Fe2(BA)(bpy)4](ClO4)4 (1) and [Fe2(BA)(phen)4](ClO4)4 (2) were further characterized by variable temperature (4.2~300 K) magnetic susceptibility measurements and the observed data were successfully simulated by the equation based on the spin Hamiltonian operator, 0200_VP_EQN_1.GIF, giving the exchange parameter J = -3.6 cm-1 for (1) and J = -7.9 cm-1 for (2). These results are commensurate with weak antiferromagnetic spin-exchange interaction between the two Fe(III) ions within each molecule. The influence of halogen substituents in the bridging ligand on magnetic interactions between the metal ions of this kind of complexes is also discussed.


181-189

Synthesis of New Co(III) Hetero-Ligand
Complexes with Imidazole and 1-Methylimidazole
and Their
1H, 13C and 59Co NMR Spectra

by E. Danilczuk1, A. Grzelakowska2 and M. Michalska3

1Faculty of Chemical Technology and Engineering, Department of Inorganic Chemistry
2Faculty of Agriculture, Department of Environmental Chemistry,
University of Technology and Agriculture, 85326 Bydgoszcz, Poland
3Department of Chemistry, Nicolaus Copernicus University, 87-100 Toruń, Poland

(Received July 5th, 1999; revised manuscript September 22nd, 1999)

cis-[Co(en)2(1-MeIm)2]Cl3, fac-[Co(dien)(ImH)3]X3 (X = Cl, 0200_VP_EQN_2.GIF, 0200_VP_EQN_3.GIF) and fac-[Co(dien)(1-MeIm)3]Cl3 complexes were prepared and characterized by absorption, 1H NMR, 13C NMR and 59Co NMR spectra, where en, dien, ImH and 1-MeIm denote ethylenediamine, diethylenetriamine, imidazole and 1-methylimidazole, respectively. Calculated coordination-induced shifts (dcomplexed dfree) ranged from +0.62 to –0.03 ppm for 1H and +7.11 to –1.19 ppm for 13C nuclei of imidazole ligands. The influence of imidazole methylation on 59Co NMR spectra was considered.


191-198

The Synthesis, Spectroscopic Characterization,
Crystal and Molecular Structure
of [ReBr
3(NO)(dppe)]0.60[ReBr4(dppe)]0.40

by J.O. Dzięgielewski1, B. Machura1, J. Małecki1,
T.J. Bartczak
2 and W. Czurak2

1Department of Inorganic and Radiation Chemistry, Institute of Chemistry, University of Silesia,
Szkolna 9, 40-006 Katowice, Poland

2X-Ray Crystallography Laboratory, Institute of General and Ecological Chemistry,
Technical University of ŁódŸ, Żeromskiego 116, 90-924 ŁódŸ, Poland
e-mail: tadekbar@ck-sg.p.lodz.pl.

(Received September 3rd, 1999; revised manuscript October 29th, 1999)

[ReOBr3(dppe)] (where dppe denotes Ph2PCH2CH2PPh2) reacts with gaseous nitric oxide in the presence of an excess of free PPh3 to give [ReBr3(NO)(dppe)]0.60[ReBr4(dppe)]0.40, characterized by X-ray crystallography, IR, UV-Vis, and magnetochemical measurements. The complex is a paramagnetic compound with magnetic moment 2.54 MB.


199-206

Synthesis and Characterization of Thiocyanato-Bridged Heteropolynuclear Chromium(III)–Copper(II) Complexes

by L. Dobrzańska1, G. Wrzeszcz1, A. Grodzicki1 and F. Rozpłoch2

1Faculty of Chemistry, Gagarina 7 and 2Institute of Physics, Grudziądzka 5/7,
Nicholas Copernicus University, 87-100 Toruń, Poland

(Received October 4th, 1999; revised manuscript November 17th, 1999)

Heteropolynuclear thiocyanato-bridged complexes were prepared in the reactions of aqueous solutions of K3[Cr(NCS)6] with copper(II) complexes of the type [CuX4]2+, where X = imidazole (imH), 4-methylimidazole (4-MeimH) and 2X = ethylenediamine (en). Solid products were formulated as (Cu(imH)4)3(Cr(NCS)6)2×2H2O, (Cu(4-MeimH)4)3(Cr(NCS)6)2·3H2O and (Cu(en)2)3(Cr(NCS)6)2·H2O on the basis of elemental analysis and spectral data (IR, UV-VIS). EPR spectra, variable temperature magnetic susceptibility and thermal properties in air were investigated, indicating that all complexes are polynuclear with thiocyanate bridges, exhibiting Curie-Weiss behavior between 80–300 K. Thermal decomposition is multistage and yields CuO and CuCrO2 as final products.


207-217

Furo[2,3-b]pyrrole Derivatives.
Syntheses and Reactions in the Furan and Pyrrole Ring

by R. Sleziak1, A. Krutošíková1, M.K. Cyrański2 and T.M. Krygowski2

1Department of Organic Chemistry, Faculty of Chemical Technology, Slovak University of Technology, SK 812 37 Bratislava, Slovak Republic
2Department of Chemistry, University of Warsaw, L. Pasteura 1, 02-093 Warsaw, Poland

(Received June 7th, 1999; revised manuscript October 25th, 1999)

6-Substituted furo[2,3-b]pyrrole-5-carboxylic acids 2b–d as well as their 2-formyl- substituted derivatives 4a–d have been prepared by alkaline hydrolysis of the corresponding esters 1b–d and 3a–d, respectively. A different behaviour of methyl 6H-furo[2,3-b]pyrrole-5-carboxylate 1a in comparison with the 4H-furo[3,2-b]pyrrole isomer has been discussed in a framework of different acidity of proton of NH group. The hypothesis has been supported by ab initio B3LYP/6-311+G** DFT calculations. The 2-formylated derivatives 3b–d were used for synthesis the propenoic acids 5b–d, the corresponding acid azides 6b–d, new disubstituted ureas 9 or 10, 2-cyano-derivatives 11a–d, which were transformed into the corresponding amidines 12 and substituted arylureas 13 as well as to 5¢-tetrazolyl derivative 14. Further methyl 2-triphenylmethyl-6H-furo[2,3-b]pyrrole-5-carboxylate 15 and its Michael addition product 16 were prepared.


219-225

Fragments of a Proline-Rich Polypeptide Settled
on a Hexapeptide Carcass Constructed of Glycine and
L-Lysine Residues. Synthesis and Biological Properties

by I. Wirkus-Romanowska1, H. Miecznikowska1, A. Zabłocka2,
K. Rybka
2, W. Fortuna2, R. Międzybrodzki2, S. Szymaniec2,
M. Janusz
2, J. Lisowski2 and G. Kupryszewski1

1Faculty of Chemistry, University of Gdańsk, 80-952 Gdańsk, Sobieskiego 18, Poland
2Institute of Immunology and Experimental Therapy, Polish Academy of Sciences,
53-114 Wrocław, Rudolfa Weigla 12, Poland

(Received September 17th, 1999; revised manuscript October 25th, 1999)

Proline-rich polypeptide fragments settled on a hexapeptide constructed of L-lysine and glycine residues were synthesized by the solid phase method: X–Lys(X)-Gly–Lys(X)-Gly–Lys(X)-Gly–OH, X = Tyr-Val-Pro-Leu-Phe-Pro and Y–Lys(Y)-Gly–Lys(Y)-Gly–Lys(Y)-Gly–OH, Y = Val-Glu-Ser-Tyr-Val-Pro-Leu-Phe-Pro. Immunotropic activity of the analogues was determined in a murine system using resistance to hydrocortisone and in human cell cultures using induction of cytokines as indicators.


227-230

Simple Synthesis of 2-Thioglycosyl Derivatives
of Pyridine N-Oxide

by G. Pastuch and W. Szeja

Silesian Technical University, Department of Chemistry, ul. Krzywoustego 8, 44-100 Gliwice, Poland

(Received July 26th, 1999; revised manuscript November 4th, 1999)

A new class of “latent” glycosyl donors, 2-thioglycosyl pyridine N-oxides was synthesized from 1-thiosugar and 2-bromopyridine N-oxide in the reaction of aromatic nucleophilic substitution of halogen.


231-238

Iodide Ion-Selective PVC Membrane Electrode Based
on a Recently Synthesized Salen–Mn(II) Complex

by M. Shamsipur1, S. Sadeghi2, H. Naeimi3 and H. Sharghi3

1Department of Chemistry, Razi University, Kermanshah, Iran
2Department of Chemistry, Shahid Beheshti University, Tehran, Iran
3Department of Chemistry, Shiraz University, Shiraz, Iran

(Received June 7th, 1999; revised manuscript September 6th, 1999)

A new PVC membrane electrode for iodide ions based on a recently synthesized salen–Mn(II) complex as membrane carrier was prepared. The electrode exhibits a Nernstian slope of 59.0±0.4 mV per decade for I over a wide concentration range (1.0×10–1–3.4×10–5 M). It has a relatively fast response time of about 20 s and can be used for at least three months without any divergence in potential. The proposed sensor shows a fairly good discriminating ability towards I ion in comparison to other common anions. The electrode can be used in the pH range 3.5–8.5. It was used as an indicator electrode in potentiometric titration of iodide ion.


239-244

Thermodynamics of Substituted Pyrazolone. VI. Potentiometric and Conductometric Studies
of Complexes of Some Transition Metals
with 4-(4-Acetophenyl)hydrazono-3-methyl-1-
-phenyl-2-pyrazolin-5-one

by A.A. El-Bindary, A.Z. El-Sonbati and H.M. Kera

Chemistry Department, Faculty of Science (Demiatta), Mansoura University, Demiatta, Egypt

(Received August 24th, 1999; revised manuscript November 16th, 1999)

The dissociation constant of 4-(4-acetophenyl)hydrazono-3-methyl-1-phenyl-2-pyra- zolin-5-one (AHMPP) has been determined potentiometrically in 0.1 M KCl and 50% (v/v) ethanol-water mixture. Also, the stepwise stability constants of the formed complexes of 0200_VP_EQN_4.GIF, Co2+, Ni2+, Cu2+, Zn2+, La3+, Ce3+, 0200_VP_EQN_5.GIFand Th4+ with AHMPP have been determined. The stability of the formed complexes follow the sequence:

Th4+ > 0200_VP_EQN_6.GIF> Ce3+ > La3+ > Mn2+ < Co2+ < Ni2+ < Cu2+ > Zn2+

The thermodynamic parameters (DG, DH and DS) for AHMPP and its complexes were evaluated and discussed. The dissociation process is nonspontaneous, endothermic and entropically unfavourable. The formation of the metal complexes has been found to be spontaneous, exothermic or endothermic (depends on the metal) and entropically favourable. The stoichiometries of these complexes were determined conductometrically indicating the formation of 1:1 and 1:2 (metal:ligand) complexes.


245-256

Ab Initio Calculations of the Pairing of Four Canonical DNA Bases with Three Thymine Derivatives Generated by Hydroxyl Radical in Anaerobic Conditions

by P. Cysewski

L. Rydygier Medical University in Bydgoszcz, Department of Physical Chemistry,
Skłodowskiej-Curie 9, 85-094 Bydgoszcz, Poland

(Received February 12th, 1999; revised manuscript September 22nd, 1999)

The coding properties of three hydroxyl radical induced thymine derivatives: 5-hydroxy-6-hydrothymine (1), 5,6-dihydrothymine (2) and 6-hydroxy-5,6-dihydrothymine (3) were characterized by ab initio HF/6-31G, HF/6-31G**//HF/6-31G and SCI-PCM/6-31G**//HF/6-31G quantum chemistry calculations. All studied derivatives may have potential miscoding character, which strongly depends on the polarity of the environment. Under non-polar conditions all analyzed thymine derivatives are able to pair with guanine, what may result in the T ® C transition. Additionally, 1 is able to form stable pairs with cytosine and adenine. Compound 3 is capable to pair with all four canonical DNA bases. All these pairs are more stable than standard AT pair. In polar environment the pairing potential of studied thymine derivatives is significantly reduced. However, the mispairing potential is usually the same and remained significant, especially for 6-hydroxy-6-hydrothymine.


257-263

Gas-Liquid Chromatographic Interactions
for Twelve Benzene-Derived Chemical Functions
on Twelve Polar Stationary Phases

by J.M. Santiuste

Institute of Physical Chemistry “Rocasolano”, CSIC, Department of Structure and Molecular Dynamics, C. Serrano, 119, 28006-Madrid, Spain

(Received November 16th, 1998; revised manuscript October 25th, 1999)

Linear solvation energy relationship (LSER) was used to describe the solute–solvent interactions of benzene and twelve derivatives on 12 stationary phases taken from literature. The hydrogen-bond interactions between the basic solute and the acid solvent were negligible, the more relevant interactions being cavity-formation/dispersion and the dipolar interactions. The effect of the polarity of both the stationary phase (solvent) and the solute (chemical function) on interactions has been investigated. The dipolar interaction increases for each solute with increasing phase polarity and for each phase with increasing solute polarity, whereas the cavity-formation/dispersion interaction decreases with increasing stationary phase polarity. The plots of the cavity-formation/dispersion and of dipolar interaction increments between chemical functions and parent benzene molecule versus stationary phase polarity confirm the above trends.


265-273

The Crystal, Molecular and Electronic Structure
of [ReBr
2(NO)(CO)(PPh3)2]×NO Complex

by T.J. Bartczak1, W. Czurak1, J.O. Dzięgielewski2,
B. Machura
2, J. Kusz3 and J. Warczewski3

1X-Ray Crystallography Laboratory, Institute of General and Ecological Chemistry,
Technical University of ŁódŸ, Żeromskiego 116, 90-924 ŁódŸ, Poland
e-mail: tadekbar@ck-sg.p.lodz.pl

2Department of Inorganic and Radiation Chemistry, Institute of Chemistry and
3Institute of Physics, University of Silesia, Uniwersytecka 4, 40-006 Katowice, Poland

(Received September 3rd, 1999; revised manuscript October 29th, 1999)

A new rhenium nitrosyl complex [ReBr2(NO)(CO)(PPh3)2]×NO has been synthesized and characterized by X-ray diffraction, IR, UV-Vis and magnetochemical measurements. The Re atom is of six-coordinate distorted octahedral configuration and linear nitrosyl ligand is trans towards the bromine ligand and cis towards CO molecule.


275-280

Synthesis and Structure
of [NH
2(C2H5)2]4[0200_VP_EQN_7.GIFO42(H2O)]×2H2O

by Q.X. Zeng1, J.Q. Xu1, G.Y. Yang1, Y.J. Song1, Y.S. Pak3, Y.H. Xing1,
R.Z. Wang
1, D.M. Li1, Y. Xing2, Y.H. Lin2 and H.Q. Jia2

1Department of Chemistry, Jilin University, Changchun 130023, P.R. China

2Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun, Jilin 130022, P.R. China

3Ham Hung Chemical Industrial University, D. PR. K

(Received May 20th, 1999; revised manuscript August 30th, 1999)


281-283

A New Lupane-Type Triterpenoid
from
Taraxacum officinale

by W. Kisiel1, B. Barszcz1 and E. Szneler2

1Department of Phytochemistry, Institute of Pharmacology, Polish Academy of Sciences,
 12 Smętna Street, 31-343 Kraków, Poland
2Department of Chemistry, Jagiellonian University, 3 Ingardena Street, 30-060 Kraków, Poland

(Received November 2nd, 1999)


285-287

Synthesis and Crystal Structure of Tetrakis(trifluoroacetato) Bis(acetone) Dirhodium(II)

by Q.-H. Zhao1, W.-M. Bu2, D.-Z. Liao1, Z.-H. Jiang1 and S.-P. Yan1

1Department of Chemistry, Nankai University, Tianjin, 300071, P. R. China
2Key Laboratory for Supramolecular Structure and Spectroscopy, Jilin University,
Changchun, 130023, P. R. China

(Received October 20th, 1999; revised manuscript November 24th, 1999)





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