POLISH JOURNAL OF CHEMISTRY
Volume 73 Number 5 May 1999
Pages 759-893


CONTENTS



Page


 

 

 

INORGANIC CHEMISTRY

759

Preparation, Spectral Properties and Antimicrobial Effects of New Cu(II) Compounds with Some Bio-Active Ligands
- Mojumdar S.C., Hudecova D. and Melnik M.

765

Phase Relations in the CuGaTe2-HgTe and CuInTe2-HgTe Systems
-ParasyukO.V., Olekseyuk I.D., Morenko A.O. and Gorgut G.P.

773

The Crystal Structure of Bis(ethylammonium) Pentachloroantimonate(III)-ethylammonium Chloride C2H5NH3)2SbCl5.(C2H5NH3)Cl at 295 and 90 K. On the Deformation of the Octahedral Coordination of SbIII
- Bujak M. and Zaleski J.

 

 

 

ORGANIC CHEMISTRY

783

Structure and Activity Studies of Glycine Receptor Ligands. Part 4. N-[(7-Arylalkyl, 7-aryloxyalkyl)-8-theophyllyl]-glycines
- Drabczyńska A., Karolak-Wojciechowska J. and Kieć-Kononowicz K.

793

New Derivatives of a- and b-Dithiophosphates of 2-Bromo-2-deoxy Sugars
-Borowiecka J.

799

Synthesis of 4-Nitroimidazole Nucleosides from 1,4-Dinitroimidazoles and D-Ribosylamines
- Walczak K.

 

 

 

PHYSICAL CHEMISTRY

805

Morphology and Activity of Zirconia-Sulfate Aerogels
- Mrowiec-Białoń J., Pajšk L., Marczewski M., Lachowski A. and Jarzębski A.B.

813

C-13 Isotope Effects in the Decarboxylation of Phenylpropiolic Acid (PPA) in Water Solution of Formic Acid (FA), in Pure Water and the Related C-13 Kinetic Isotope Effect in the De-carbonylation of Formic Acid in Water Solution of Formic Acid and Phenylpropiolic Acid
- Zieliński M., Zielińska A., Ogrinc N., Kobal I., Paul H., Bernasconi S. and Papiernik-Zielińska H.

 

 

 

CRYSTAL AND MOLECULAR STRUCTURE

821

X-ray Investigations of Four Selected Multifunctional Phenylsulfones
- Gałdecka E. and Gałdecki Z.

845

Crystal and Molecular Structures of 1,1-Bis(methylthio)-4-(2-pyridyl)-2,3,5-triaza-1,3-pentadiene and Its 5-Phenyl Derivative
- Główka M.L., Martynowski D., Olczak A., Kozłowska K., Ołubek Z., Orlewska C. and Foks H.

853

Molecular Ribbons in the Crystals of a New Cu(II) Complex with Pyrazine-2,3-dicarboxylate Ligand
- Ptasiewicz-Bšk H. and Leciejewicz J.

859

Structure of Three Selected Dirhodium(II) and Cobalt(II) Phosphane Complexes
- Gałdecki Z., Gałdecka E., Kowalski A., Pruchnik F.P., Wajda-Hermanowicz K. and Starosta R.

 

 

 

COMMUNICATIONS

873

Cu(II) Complexes with Rutin
- Dyba M., Solinas S., Culeddu N., Ganadu M.-L. and Kozłowski H.

879

Synthesis and Circular Dichroism Studies of HIV-1 Tat Arginine Rich Domain Analogues Substituted in Arg 52 Position
- Szyk A., Mucha P., Rekowski P., Giel-Pietraszuk M. and Barciszewski J.

885

X-ray Investigation of the Ternary Nd-Zn-(Sn, Pb) Systems
- Salamakha P., Demchenko P., Sologub O. and Bodak O.

889

Synthesis and Properties of the Complexes of Lanthanides with Nitronyl Nitroxides
-Wang Z., Zhao Q.H., Liao D.Z., Jiang Z.H., Yan S.P. and Wang G.L.

893

IUPAC Recommendations on Nomenclature and Symbols


ABSTRACTS


759-764

Preparation, Spectral Properties and Antimicrobial Effects of New Cu(II) Compounds with Some Bio-Active Ligands

by S.C. Mojumdar1, D. Hudecova2 and M. Melnik3


1Institute of Inorganic Chemistry, Slovak Academy of Sciences, SK-84236 Bratislava, Slovakia
E-mail: uachmoju@savba.sk
2Department of Biochemistry and Microbiology, Faculty of Chemical Technology,
Slovak University of Technology, SK-81237 Bratislava, Slovakia
3Department of Inorganic Chemistry, Faculty of Chemical Technology,
Slovak University of Technology, SK-81237 Bratislava, Slovakia

(Received November 11th, 1998; revised manuscript January 11th, 1999)

The compounds [Cu(ac)2(Et2na)]2.Et2na.2H2O (I), Cu(Clac)2(Et2na)3 (II), Cu(Cl2ac)2(Et2na)2.2H2O (III), [Cu(ac)2mpc]2.2CH3OH (IV), Cu(Clac)2(mpc) (V), Cu(Cl2ac)2(mpc)2 (VI), Cu(Cl3ac)2(mpc)2 (VII), Cu(pc).5H2O (VIII), where ac = CH3COO-, Clac = ClCH2COO-, Cl2ac = Cl2CHCOO-, Cl3ac = Cl3CCOO-, Et2na = N,N-diethylnicotinamide, mpc = methyl-3-pyridyl carbamate and pc = 2,6-pyridinedicarboxylate have been prepared and characterized by elemental analysis, IR, EPR and electronic spectra. Their antimicrobial effects have been tested on various fungal strains. Significant morphological changes of Botrytic cinerea were observed by the compounds V and VII. The highest antimicrobial effects were manifested by compound IV. IC50 and MIC of that compound are 220 and 1000 mg/ml against Rhizopus oryzae, 250 and 500 mg/ml against Microsporum gypseum, respectively. IR data suggest a unidentate coordination of carboxylate to Cu(II). Et2na and mpc were coordinated through the N atom of the heterocyclic rings. EPR spectra suggest a dimeric structure of complexes I and IV and monomeric structure of complexes II, III, V-VIII.

765-772

Phase Relations in the CuGaTe2-HgTe and CuInTe2-HgTe Systems

by O.V. Parasyuk, I.D. Olekseyuk, A.O. Morenko and G.P. Gorgut


Department of Inorganic and Physical Chemistry, Volyn State University,
Voli av. 13, Lutsk 263009, Ukraine

(Received December 1st, 1998; revised manuscript January 21st, 1999)

Phase equilibria in the CuGaTe2-HgTe and CuInTe2-HgTe systems are investigated by differential thermal, X-ray phase and microstructural analyses. Both systems are of quasibinary, peritectic type, resulting in the formation of solid solutions. Solid solubility in HgTe varies from 0-31 mol% for CuGaTe2 and from 0-64 mol% for CuInTe2. The solid solution based on CuInTe2 does not exceed 4 mol% HgTe and the one based on CuGaTe2 contains less than 2 mol% HgTe.

773-782

The Crystal Structure of Bis(ethylammonium) Pentachloroantimonate(III)-ethylammonium Chloride (C2H5NH3)2SbCl5.(C2H5NH3)Cl at 295 and 90 K. On the Deformation of the Octahedral Coordination of SbIII

by M. Bujak and J. Zaleski


Institute of Chemistry, University of Opole, Oleska 48, 45-052 Opole, Poland
E-mail: zaleski@uni.opole.pl

(Received December 28th, 1998; revised manuscript January 29th, 1999)

Bis(ethylammonium) pentachloroantimonate(III)-ethylammonium chloride belongs to alkylammonium chloroantimonates(III). The anionic sublattice of (C2H5NH3)2SbCl5.(C2H5NH3)Cl is built of isolated Sb2Cl104- units composed of two SbCl63- octahedra, connected by edge and two single chlorine Cl- ions. There are three crystallographically non-equivalent ethylammonium cations, two of them are disordered at room temperature and all of them are ordered at 90 K. The disorder is realized by two positions for carbon atoms. Ethylammonium cations are connected to the anionic sublattice by N-H...Cl hydrogen bonds. The influence of temperature and hydrogen bonds together with electrostatic interactions on the deformation of the octahedral coordination of SbIII is discussed.

783-792

Structure and Activity Studies of Glycine Receptor Ligands. Part 4.
N-[(7-Arylalkyl,7-aryloxyalkyl)-8-theophyllyl]-glycines

by A. Drabczyńska1, J. Karolak-Wojciechowska2 and K. Kieć-Kononowicz1


1Department of Chemical Technology of Drugs, Collegium Medicum of Jagiellonian University,
Medyczna 9, 30-688 Kraków, Poland
2
Institute of General and Ecological Chemistry, Technical University, Żwirki 36, 90-924 ŁódŸ, Poland

(Received October 8th, 1998; revised manuscript January 22nd, 1999)

Preparation of N-[(7-arylalkyl,7-aryloxyalkyl)-8-theophyllyl]-glycines by condensation of 8-bromo-theophylline with arylalkyl- and aryloxyalkylbromides and aminolysis with glycine is described. The structure of one of the obtained glycine derivatives was confirmed by X-ray analysis. A comparison of the glycine receptor binding model (molecule L-689,560) and the 3-D structure of that molecule indicates serious differences in molecule shape, explaining their inactivity.

793-798

New Derivatives of a- and b-Dithiophosphates of
2-Bromo-2-deoxy Sugars

by J. Borowiecka


Laboratory of Organic Chemistry, Institute of Chemistry, Medical University,
Muszyńskiego 1, 90-151 ŁódŸ, Poland

(Received November 19th, 1998; revised manuscript January 22nd, 1999)

New derivatives of 2-bromo-2-deoxy hexopyranose, a- and b-glycosyl dithiophosphates 6-11, were synthesized by three methods: (A) by glycosylation of alkyl salts 1-3 of phosphorodithio acids with a-1,2-D-gluco and a-1,2-D-manno dibromides 4, 5; (B) by reaction of 4 or 5 with free phosphorodithio acids 12-14 activated by Lewis acid; (C) by addition of dithioacids 12-14 to 2-bromo-D-glucal 15.

799-804

Synthesis of 4-Nitroimidazole Nucleosides from
1,4-Dinitroimidazoles and D-Ribosylamines

by K. Walczak


Institute of Organic Chemistry and Technology, Silesian Technical University,
Krzywoustego 4, 44-101 Gliwice, Poland

(Received December 3rd, 1998; revised manuscript January 25th, 1999)

Reaction of D-ribopyranosylamine or 2,3-O-isopropylidene-D-ribofuranosylamine with 1,4-dinitroimidazoles in aqueous methanol affords appropriate 4-nitroimidazole nucleoside derivatives.

805-812

Morphology and Activity of Zirconia-Sulfate Aerogels

by J. Mrowiec-Białoń1, L. Pajšk, M. Marczewski3, A. Lachowski1 and A.B. Jarzębski

1Institute of Chemical Engineering, Polish Academy of Sciences, 44-100 Gliwice, Bałtycka 5, Poland
2Silesian University, Institute of Physics and Chemistry of Metals, 40-131 Katowice, Poland
3Warsaw University of Technology, Faculty of Chemistry, 00-664 Warsaw, Poland
4Silesian Technical University, Institute of Chemical Engineering, 44-100 Gliwice, Poland

(Received November 9th, 1998; revised manuscript January 18th, 1999)

Zirconia-sulfate aerogels obtained from the process with the molar hydrolysis ratio r = 4 are more porous and active than those synthesized with r = 2. Sulfate ions markedly hinder sintering of zirconia and structure consolidation during heat treatment and this process depends on their concentration. At a higher sulfate load (20 mol% of SO42- in ZrO2) zirconia is amorphous upon calcination at 773 K, irrespective of the water content in the synthesis, while at a lower load it can be crystalline. XRD analysis indicates that the crystalline phase of calcined zirconia-sulfate is cubic and not tetragonal, as observed in conventional zirconia, and reported in previous studies. Acid strength of ZrO2-SO42- system appears comparable to that of AlCl3/Al2O3, but lower than that of SbF5/Al2O3.

813-820

C-13 Isotope Effects in the Decarboxylation of Phenylpropiolic Acid (PPA) in Water Solution of
Formic Acid (FA), in Pure Water and the Related C-13 Kinetic Isotope Effect in the Decarbonylation of Formic Acid in Water Solution of Formic Acid and Phenylpropiolic Acid

by M. Zieliński1, A. Zielińska1, N. Ogrinc2, I. Kobal2, H. Paul3,
S. Bernasconi3 an
d H. Papiernik-Zielińska1


1Faculty of Chemistry, Jagiellonian University, 30-060 Cracow, Poland
2Josef Stefan Institute, Ljubljana, Slovenia
3Laboratory of Stable Isotopes, Institute of Geology, E.T.H., Zurich, Switzerland

(Received October 26th, 1998; revised manuscript February 19th, 1999)

Kinetics and the carbon-13 kinetic isotope effects in the decarboxylation of phenylpropiolic acid in HCOOH/H2O, 1:1/V:V, solution have been examined between 80-140.13oC. 13C KIE in the decarbonylation of formic acid, proceeding with measurable rate in this medium between 130-150oC, has been determined also and compared with corresponding values found in the pure HCOOH/H2O solution. Kinetics and C-13 KIE in the decarboxylation of phenylpropiolic acid in pure water have been investigated subsequently between 100-143 oC in all glass reaction vessels sealed under vacuum. The enthalpy of activation of decarboxylation of PPA in pure water, 30.20 kcal/mol, and the entropy of activation, DSš = -3.7 e.u., are by 6.7 kcal/mol and 12.5 e.u., respectively, higher than the DH# and DS# values found in the decarboxylation of PPA in pure formic acid. The C-13 KIE equal to 1.004-1.005 between 70-100oC in the pure HCOOH medium increased to C-13 KIE of 1.020 in the case of decarboxylation of PPA at 133.7 oC in the initially pure water.

821-844

X-ray Investigations of Four Selected
Multifunctional Phenylsulfones

by E. Gałdecka1 and Z. Gałdecki2


1Institute of Low Temperature and Structure Research, Polish Academy of Sciences,
ul. Okólna 2, 50-950 Wrocław, Poland
2Institute of General and Ecological Chemistry, Technical University of ŁódŸ, ul. Żwirki 36, 90-924 ŁódŸ, Poland

(Received October 1st, 1998; revised manuscript January 13th, 1999)

The crystal and molecular structures of following selected multifunctional phenylsulfones were determined by X-ray diffraction methods using an Enraf-Nonius CAD4S diffractometer: a-(4-biphenylsulfonyl)acetophenone, (I); a-methyl-a-[4-(acetylamino)phenylsulfonyl]acetophenone, (II); 1,1-dichloro-2-phenyl-2-(4-allylsulfonylphenyl)ethene, (III); 1,1-dichloro-2-phenyl-2-(4-chlorosulfonylphenyl)ethene, (IV). The compound (I), (C20H16O3S), crystallizes in the monoclinic P21/c space group with unit cell dimensions: a = 9.0527(6) A, b = 5.333(1) A, c = 34.286(2) A, b= 94.796(5)o. Analysis of benzene-ring geometry leads to the conclusion that the bond angles and distances within the benzene rings of the four investigated structures seem normal, and only small deviations occur. In (I) all three rings are almost planar and the two rings in the biphenyl are almost coplanar. The compound (II), (C17H17NO4S), crystallizes in the monoclinic P21/c space group with unit cell dimensions: a = 10.943(4) A, b = 8.566(2) A, c = 17.286(4) A, b= 90.57(3)o. Both rings are almost planar. The compound (III), (C17H14O2SCl2), crystallizes in the monoclinic P21/c space group with unit cell dimensions: a = 12.577(20) A, b = 18.961(2) A, c = 7.407(2) A, b= 103.83(2)o. Both rings are almost planar - the dihedral angles in ring A vary from -1.7o to 1.2o, and in ring B from -1.7o to 1.6o. The planes of the two rings are nearly perpendicular to each other. The compound (IV), (C14H9O2SCl3), crystallizes in the monoclinic P21/n space group with two independent molecules in the unit cell (Z = 8), and with unit cell dimensions: a = 9.0527(6) A, b = 5.333(1) A, c = 34.286(2) A, b= 94.796(5)o. The two molecules are related to an approximative non-crystallographic symmetry centre. All four rings are almost planar. The increase of the bond angles at C11 and C31 atoms is caused by the high electronegativity of the SO2 group. The A and B rings and the C and D rings are almost perpendicular to each other. The respective bond lengths and angles of the two independent molecules are very similar. The phenacyl phenyl sulphone derivatives are examples of a system with acidic C-H bonds. In such interesting systems many weak interactions (and/or very weak hydrogen bonds C-H...O (or C-H...N) occur. This is often observed in biologically active compounds (for example nucleosides). In the crystal of (I) there are 10 such interactions (6 intermolecular and 4 intramolecular). In the crystal of (II) there are 11 such interactions (6 intermolecular and 5 intramolecular). In the crystal of (III) there are 5 such interactions (3 intermolecular and 2 intramolecular). In the crystal of (IV) there are 10 such interactions (6 intermolecular and 4 intramolecular).

845-852

Crystal and Molecular Structures of 1,1-Bis(methylthio)-4-(2-pyridyl)-2,3,5-triaza-1,3-pentadiene and Its 5-Phenyl Derivative

by M.L. Główka1, D. Martynowski1, A. Olczak1, K. Kozłowska1, Z. Ołubek1, C. Orlewska2 and H. Foks2


1Institute of General and
Ecological Chemistry, Technical University of ŁódŸ,
ul. Żwirki 36, 90-924 ŁódŸ, Poland
2Department of Organic Chemistry, Medical University of Gdańsk,
Al. Gen. J. Hallera 107, 80-416 Gdańsk, Poland

(Received November 9th, 1998; revised manuscript January 18th, 1999)

Structures of the two dimethylthiomethylene-2-pyridinecarboxamide hydrazones have been examined spectroscopically and by X-ray diffraction to establish the dominant tautomeric form and conformation. The two crystal structures are very similar with approximately planar conformation and intramolecular hydrogen bond between 4-imine group as hydrogen donor and pyridyl N atom as an acceptor. Several significant differences found may be easily explained by phenyl substitution in one of the compounds. The benzene ring in compound 2 is twisted by about 40o in relation to the mean molecular plane due to packing forces. An interesting feature of the structures is the deviation of the pyridyl ring by 11-14o from the mean 2,3,5-triaza-1,3-pentadiene plane in the two structures, despite the intramolecular hydrogen bond spanning the two fragments. It agrees with the elongation of C(4)-pyridine bond to 1.488 A, which corresponds with the lack of conjugation between p electrons of the pyridine ring and a lone pair at adjacent N(4) atom.

853-858

Molecular Ribbons in the Crystals of a New Cu(II)
Complex with Pyrazine-2,3-dicarboxylate Ligand

by H. Ptasiewicz-Bšk and J. Leciejewicz


Institute of Nuclear Chemistry and Technology, ul. Dorodna 16, 03-195 Warszawa, Poland

(Received December 12th, 1998; revised manuscript January 18th, 1999)

The structure of diaquobis(m-trans hydrogen pyrazine-2,3-dicarboxylato N,O,O')copper(II) dihydrate crystals is polymeric. The coordination polyhedron around the Cu(II) ion is an elongated octahedron. The Cu(II) ion and two symmetry related pyrazine-2,3-dicarboxylate (2,3-PZDC) ligands are coplanar and form the basic unit of this structure. Each ligand coordinates the metal with one carboxylate oxygen atom [Cu-O(1) 1.957(3) A] and the nearest heteroring nitrogen atom [Cu-N(1) 2.000(3) A]. The second carboxylic group contributes one carbonyl oxygen atom that coordinates the Cu(II) ion in an adjacent unit [Cu-O(3) 2.414(4) a], giving rise to molecular ribbons composed of Cu(2,3-PZDC)2 units interconnected by oxygen atoms. The water molecules are involved in a system of hydrogen bonds operating between the ribbons.

859-872

Structure of Three Selected Dirhodium(II) and
Cobalt(II) Phosphane Complexes

by Z. Gałdecki1, E. Gałdecka2, A. Kowalski3, F.P. Pruchnik4,
K. Wajda-Hermanowicz4 and R. Starosta4


1Institute of General and Ecological Chemistry, Technical University of ŁódŸ,
ul. Żwirki 36, 90-924 ŁódŸ, Poland
2Institute of Low Temperature and Structure Research, Polish Academy of Sciences,
ul. Okólna 2, 50-950 Wrocław, Poland
3Kuma Diffraction Ltd, ul. Akacjowa 15b, 53-122 Wrocław, Poland
4Faculty of Chemistry, University of Wrocław, ul. F. Joliot-Curie 14, 50-383 Wrocław, Poland

(Received September 11th, 1998; revised manuscript January 22nd, 1999)

The crystal structure of the following complexes has been determined using a KM4CCD Kuma Diffraction Diffractometer with CCD camera, and the original KM4CCD data collection and KM4RED data reduction programs: tetrachlorobis{m-phenylbis(2-pyridyl)phosphane(P,N,N')}dirhodium(II), [Rh2Cl4{PPh(C5H4N)2}2], (I); tris(m-acetato-kO:kO')(acetic acid-1kO)-m-2-{[(2-methoxyphenyl-2kO)(2-methoxyphenyl)phosphano-2-kP]phenolato-1kO}-dirhodium(II),[Rh2(OOCCH3)3
{P(C6H4OCH3)2C6H4O}HOOCCH3], (II); dichlorobis{phenylbis(2-pyridyl)phosphane oxide}cobalt(II), [CoCl2{OP(C5H4N)2}2(C6H5)}2], (III).

873-878

Cu(II) Complexes with Rutin

by M. Dyba1, S. Solinas2, N. Culeddu3, M.-L. Ganadu2 and H. Kozłowski1


1Faculty of Chemistry, University of Wrocław, F. Joliot-Curie 14, 50-383 Wrocław, Poland
2Dipartimento di Chimica, Universita di Sassari, 07100 Sassari, Italy
3CNR IAT CAPA, via Vienna 2, 07100 Sassari, Italy

(Received October 19th, 1998; revised manuscript January 8th, 1999)

879-884

Synthesis and Circular Dichroism Studies of HIV-1 Tat Arginine Rich Domain Analogues Substituted in Arg 52 Position

by A. Szyk1, P. Mucha1, P. Rekowski1, M. Giel-Pietraszuk2
and J. Barciszewski2


1University of Gdańsk, Department of Chemistry, Sobieskiego 18, 80-952 Gdańsk, Poland
2Institute of Bioorganic Chemistry, Polish Academy of Sciences, Noskowskiego 12, 61-704 Poznń, Poland

(Received November 24th, 1998; revised manuscript January 18th, 1999)

885-888

X-ray Investigation of the Ternary Nd-Zn-(Sn, Pb) Systems

by P. Salamakha, P. Demchenko, O. Sologub and O. Bodak


Inorganic Chemistry Department, L'viv State University, L'viv, Ukraine

(Received December 14th, 1998; revised manuscript January 18th, 1999)

889-892

Synthesis and Properties of the Complexes of
Lanthanides with Nitronyl Nitroxides

by Z. Wang1, Q.H. Zhao2, D.Z. Liao1, Z.H. Jiang1, S.P. Yan1 and G.L Wang1


1Department of Chemistry, Nankai University, Tianjin, 300071, P. R. China
2State Key Laboratory of Coordination Chemistry Nanjing University, Nanjing, 210008, P. R. China

(Received October 13th, 1998; revised manuscript February 3rd, 1999)

893

IUPAC RECOMMENDATIONS ON NOMENCLATURE AND SYMBOLS
IUBMB-IUPAC
Joint Commission on Biochemical Nomenclature (JCBN)
Nomenclature of Lignands and Neolignans


Return to main page.


(c) 1999 Polish Journal of Chemistry

prepared by (aws)