Synthesis, spectral studies, and biological activity of metal complexes of benzofuran thiosemicarbazides

Article abstract of DOI:10.1081/SIM-200030199

The complexes of Co(II), Cu(II), Ni(II), Cd(II), Hg(II), Zn(II), UO ₂(VI), and Th(IV) with benzofuran thiosemicarbazides have been prepared. All complexes have the general formula MLX_n, where n = 2 or 4, X = Cl or NO₃ and

Full text of DOI:10.1081/SIM-200030199

This article was downloaded by: [Moskow State Univ Bibliote]
On: 03 November 2013, At: 12:36
Publisher: Taylor & Francis
Informa Ltd Registered in England and Wales Registered Number:
1072954 Registered office: Mortimer House, 37-41 Mortimer Street,
London W1T 3JH, UK
Synthesis and Reactivity in
Inorganic and Metal-Organic
Chemistry
Publication details, including instructions for
authors and subscription information:
http://www.tandfonline.com/loi/lsrt19
Synthesis, Spectral
Studies, and Biological
Activity of Metal
Complexes of Benzofuran
Thiosemicarbazides
M. B. Halli a , Shashidhar a & Z. S. Qureshi b
a Department of Chemistry , Gulbarga
University , Gulbarga, 585 106, India
b Anjuman Degree College , Bijapur, India
Published online: 16 Nov 2010.
To cite this article: M. B. Halli , Shashidhar & Z. S. Qureshi (2004) Synthesis,
Spectral Studies, and Biological Activity of Metal Complexes of Benzofuran
Thiosemicarbazides, Synthesis and Reactivity in Inorganic and Metal-Organic
Chemistry, 34:10, 1755-1768, DOI: 10.1081/SIM-200030199
To link to this article: http://dx.doi.org/10.1081/SIM-200030199
PLEASE SCROLL DOWN FOR ARTICLE
Taylor & Francis makes every effort to ensure the accuracy of all
the information (the “Content”) contained in the publications on our
platform. However, Taylor & Francis, our agents, and our licensors
make no representations or warranties whatsoever as to the accuracy,
completeness, or suitability for any purpose of the Content. Any opinions
and views expressed in this publication are the opinions and views of
the authors, and are not the views of or endorsed by Taylor & Francis.

The accuracy of the Content should not be relied upon and should be
independently verified with primary sources of information. Taylor and
Francis shall not be liable for any losses, actions, claims, proceedings,
demands, costs, expenses, damages, and other liabilities whatsoever
or howsoever caused arising directly or indirectly in connection with, in
relation to or arising out of the use of the Content.
This article may be used for research, teaching, and private study
purposes. Any substantial or systematic reproduction, redistribution,
reselling, loan, sub-licensing, systematic supply, or distribution in any
form to anyone is expressly forbidden. Terms & Conditions of access
and use can be found at http://www.tandfonline.com/page/terms-and-
conditions

SYNTHESIS AND REACTIVITY IN INORGANIC AND METAL-ORGANIC CHEMISTRY
Vol. 34, No. 10, pp. 1755–1768, 2004
Synthesis, Spectral Studies, and Biological
Activity of Metal Complexes of Benzofuran
Thiosemicarbazides
M. B. Halli,1, Shashidhar,1 and Z. S. Qureshi2
*
1Department of Chemistry, Gulbarga University, Gulbarga, India
2Anjuman Degree College, Bijapur, India
ABSTRACT
The complexes of Co(II), Cu(II), Ni(II), Cd(II), Hg(II), Zn(II), UO2(VI),
and Th(IV) with benzofuran thiosemicarbazides have been prepared. All
complexes have the general formula MLXn, where n ¼ 2 or 4, X ¼ Cl or
NO3 and L is the ligand prepared by the reaction of benzofuran-2-carboxy-
hydrazide with p-methyl, p-methoxy, or p-bromophenylisothiocyanate.
The complexes were characterized on the basis of elemental analyses,
spectral, magnetic moment, and conductance studies. The ligands coor-
dinate to the metal ions through the oxygen of the arbonyl group and the
nitrogen of the hydrazine group. We have assigned the probable geome-
try for all of these complexes based on their physico-chemical data. All
*
Correspondence: M. B. Halli, Department of Chemistry, Gulbarga University,
Gulbarga 585 106, India; E-mail: mbhalli@rediffmail.com.
1755
DOI: 10.1081/SIM-200030199
0094-5714 (Print); 1532-2440 (Online)
www.dekker.com
Copyright # 2004 by Marcel Dekker, Inc.

1756
Halli, Shashidhar, and Qureshi
the metal complexes and ligands were screened for their anti-microbial
activity.
Key Words: Metal complexes; Spectral studies; Biological activity;
Benzofuran thiosemicarbazides.
INTRODUCTION
Thiosemicarbazide derivatives have been reported to possess antibacte-
rial,[1,2] antiviral,[3] and antifungal[4] activities. As a ligand they provide
three potential donor sites viz. O, N, and S and form complexes with various
transition and non-transition metal ions. The metal complexes with thio-
derivatives of the hydrazine have occupied a very important place in the
future development and progress of coordination chemistry. In the present
study, we report the thiosemicarbazide ligands derived from the reaction
between p-methylphenylisothiocyanate, p-methoxyphenylisothiocyanate or
p-bromophenylisothiocyanate, and benzofuran-2-carboxyhydrazide with a
view that benzofuran thiosemicarbazide derivatives and their metal complexes
might exhibit high biological activity compared with benzofurans[5] or thio-
semicarbazides alone. The metal ions used are Co(II), Cu(II), Ni(II), Cd(II),
Hg(II), Zn(II), UO2(VI), and Th(IV).
EXPERIMENTAL
All the chemicals used were of analytical grade. The metal, chloride, and
nitrogen contents in the complexes were determined by standard methods.[6]
The physical methods used were the same as reported earlier.[7] The ligands
benzofuro-2-carboxy-[40-methylphenyl] thiosemicarbazide (BCMePT), ben-
zofuro-2-carboxy-[40-methoxyphenyl] thiosemicarbazide (BCMeOPT), and
benzofuro-2-carboxy-[40-bromophenyl] thiosemicarbazide (BCBrPT) were
synthesized by the following method.
Preparation of Thiosemicarbazide Ligands
The thiosemicarbazide ligands are prepared by the reaction of
benzofuran-2-carboxyhydrazide (2.18 g, 5 mmol) in ethyl alcohol (25 mL)
and p-methylphenylisothiocyanate (1.11 g, 5 mmol) or p-methoxyphenyl-
isothiocyanate (1.25 g, 5 mmol) or p-bromophenylisothiocyanate (1.69 g,
5 mmol) in ethyl alcohol (10 mL). The reaction mixture was refluxed on a
water bath for about 2 hr. The thiosemicarbazide ligands separated out on

Metal Complexes of Benzofuran Thiosemicarbazides
1757
cooling to room temperature and were filtered, washed with ethyl alcohol,
recrystallised from ethyl alcohol, and dried in vacuo over fused CaCl2 (analy-
tical data are shown in Table 1).
Preparation of Metal Complexes
The metal complexes were prepared by reacting the thiosemicarbazide
ligand (1.62 g, BCMePT; 1.7 g, BCMeOPT; 1.95 g, BCBrPT, 1 mmol) in
ethyl alcohol (50 mL) with the corresponding metal chlorides or nitrates
(1 mmol) in ethyl alcohol (15 mL). The reaction mixture was refluxed on a
water bath for about 3 hr during which time solid complexes separated.
In the case of the Zn(II), Cd(II), and UO2(VI) complexes the pH of the solution
was adjusted to 5–6 by adding 50% (2–3 mL) aqueous alcoholic solution
of sodium acetate. The reaction mixture was cooled to room temperature,
the solid complexes filtered, washed with alcohol, and water to remove the
unreacted metal salts and ligands. The complexes were dried in a vacuum
over fused CaCl2.
RESULTS AND DISCUSSION
All complexes gave satisfactory N, M, and Cl analysis. The formation of
the ligands and complexes (Fig. 1) may be represented by the following
equations.
EtOH, reflux, 2hr
nCuCl2 ꢀ 2H2O þ nL ꢁꢁꢁꢁꢁꢁꢁꢁꢁꢁꢁꢁꢁꢁ! ½CuLCl2ꢂn þ 2H2O
ðL ¼ BCMePT or BCMeOPT or BCBrPTÞ
ð1Þ
Table 1. Analytical data of the benzofuran thiosemicarbazide ligands.
Anal. %, Found (calcd.)
Molecular
formula
Formula
weight
Yield
(%)
M.p.
(8C)
C
H
N
[BCMePT]
325.00
341.00
390
80
85
85
225
250
270
62.50
(62.70)
59.65
4.60
(4.61)
4.12
15.80
(16.00)
15.00
C17H15N3O2S
[BCMeOPT]
C17H15N3O3S
[BCBrOPT]
(59.82)
49.50
(49.23)
(4.39)
4.20
(3.07)
(15.24)
10.60
(10.76)
C16H12BrN3O2S

1758
Halli, Shashidhar, and Qureshi
Figure 1. Synthesis and structure of the ligands.
EtOH, reflux, 2hr
nCoCl2 ꢀ 6H2O þ nL ꢁꢁꢁꢁꢁꢁꢁꢁꢁꢁꢁꢁꢁꢁ! ½CoLCl2ꢂn þ 6H2O
ðL ¼ BCMePT or BCMeOPTÞ
ð2Þ
ð3Þ
ð4Þ
ð5Þ
ð6Þ
EtOH, reflux, 2hr
nCoCl2 ꢀ 6H2O þ nL ꢁꢁꢁꢁꢁꢁꢁꢁꢁꢁꢁꢁꢁꢁ! f½CoLCl2ꢂ ꢀ H2Ogn þ 5H2O
ðL ¼ BCBrPTÞ
EtOH, reflux, 2hr
nNiCl2 ꢀ 6H2O þ nL ꢁꢁꢁꢁꢁꢁꢁꢁꢁꢁꢁꢁꢁꢁ! ½NiLCl2ꢂn þ 6H2O
ðL ¼ BCBrPTÞ
EtOH, reflux, 2hr
nNiCl2 ꢀ 6H2O þ nL ꢁꢁꢁꢁꢁꢁꢁꢁꢁꢁꢁꢁꢁꢁ! f½NiLCl2ꢂ ꢀ H2Ogn þ 5H2O
ðL ¼ BCMePT or BCMeOPTÞ
EtOH, reflux, 2hr
nCdCl2 þ nL ꢁꢁꢁꢁꢁꢁꢁꢁꢁꢁꢁꢁꢁꢁ! ½CdLCl2ꢂn
ðL ¼ BCMePT or BCMeOPT or BCBrPTÞ

Metal Complexes of Benzofuran Thiosemicarbazides
1759
EtOH, reflux, 2hr
MCl2 þ L ꢁꢁꢁꢁꢁꢁꢁꢁꢁꢁꢁꢁꢁꢁ! ½MLCl2ꢂ
ðL ¼ BCMePT or BCMeOPT or BCBrPT and
M ¼ ZnðIIÞ or HgðIIÞÞ
EtOH, reflux, 2hr
ð7Þ
ð8Þ
nMðNO3Þx ꢀ 6H2O þ nL ꢁꢁꢁꢁꢁꢁꢁꢁꢁꢁꢁꢁꢁꢁ! ½MLðNO3Þxꢂn þ 6H2O
ðL = BCMePT or BCMeOPT or BCBrPT;
M = UO2ðVIÞ; x ¼ 2 and n ¼ 2; M = ThðIVÞ; x ¼ 4Þ
The analytical data (Table 2) indicate 1 : 1 metal : ligand ratio for all com-
plexes. All the complexes are stable towards air and light and are soluble in
DMF, DMSO, and pyridine and insoluble in common organic solvents. The
molar conductance values of the complexes in DMF (1023 M) solution fall
in the range of 8.25–18.80 ohm21 cm2 mol21. These values are too low to
account for any electrolytic behaviors of the complexes[8] (Table 2).
Electronic Spectra
In the electronic spectrum of the Co(II) complexes in DMF (1023 M)
solution, the two bands observed in the regions 17,860–18,180 and
4
4
20,000–20,830 cm21 are assigned to T1g(F) ! A2g(F) (n2) and
4
4T1g(F) ! T1g(P) (n3) transitions, respectively, in an octahedral environ-
ment.[9] The high-energy band observed around 30,000 cm21 is assigned to
metal–ligand charge transfer bands. The octahedral geometry is further
supported by the values of the ligand field parameters Dq, B0, b, b%, and
LFSE (Table 3). The reduction in the values of the Racah parameter B0
from the free ion value (971) and the b% values testify to the presence of
strong metal–ligand covalent bonding in the complexes. The magnetic
moment values of the Co(II) complexes lie in the range of 4.69–5.09
B.M. and these values are indicative of octahedral structures for these
complexes.[10]
The light-green Ni(II) complexes show two bands the regions 13,510–
3
3
14,080 and 25,320–26,040 cm21 assignable to A2g(F) ! T1g(F) (n2) and
3
3A2g(F) ! T1g(P) (n3) transitions, respectively, in an octahedral geometry
in view of earlier reports.[11] However, the n1 band could not be observed
due to the limited spectral range of the instrument and, hence, these values
were calculated using band-fitting procedures.[12] The values of the Racah
parameter B0 is less than the free ion (1040) value indicating considerable
covalent character of the metal–ligand bond. The transition ratio n2/n1
is in the range 1.61–1.82 as expected for octahedral Ni(II) complexes.

1760
Halli, Shashidhar, and Qureshi
m

Metal Complexes of Benzofuran Thiosemicarbazides
1761

1762
Halli, Shashidhar, and Qureshi
b
b

Metal Complexes of Benzofuran Thiosemicarbazides
1763
The magnetic moment values of the Ni(II) complexes are in the range of
2.98–3.21 B.M., and are evidence for an octahedral structure.[13] The bands
around 29,000 cm21 are assigned to charge transfer bands.
The Cu(II) complexes exhibit a broad asymmetric band envelop in the
2
2
region of 16,260–12,990 cm21 attributable to the Eg ! Tg transition in a
distorted octahedral environment. The broadness of the band may be due to
dynamic Jahn-Teller distortion. The magnetic values of 1.89–2.01 B.M.
further support the octahedral structures for the Cu(II) complexes.[7]
Infrared Spectra
All the ligands show three absorption bands in the regions of 3442–3431,
3227–3370, and 3158–3180 cm21 which are assigned to 4NH, 2NH, and 1NH
4
1
stretching vibrations, respectively.[14,15] The bands due to NH and NH
stretching vibrations are observed almost at the same position or shifted to
the higher wave number side by about 5–10 cm21 in some complexes,
thereby indicating no coordination through these groups with metal ions.
2
The shift to the lower wave number side observed for the NH stretching
vibrations in the spectra of all complexes by about 15–40 cm21 indicates
2
the coordination of the ligand through the nitrogen atom of the NH group.
No bands were observed above 3500 cm21 and around 2600 cm21 due to
OH and SH stretching vibrations in the free ligands which suggests that all of
the ligands exists in the thioketo form. The Ni(II) complexes of BCMePT and
BCMeOPT and the Co(II) complex of BCBrPT contain a water molecule of
hydration and this is confirmed by their weight loss when these complex on
drying in an oven at around 110 8C lose a water molecule suggesting the pre-
sence of a lattice-held water molecule and not a coordinated one. According to
Nikolaev et al.[16] water eliminated below 150 8C can be considered as lattice-
held water molecules.
The medium to strong intensity bands observed in the region 1657–
1680 cm21 in the free ligands are assigned to C55O stretching vibrations.[17]
These bands shift to the lower wave number side by about 20–50 cm21 in
the complexes suggesting the coordination of the oxygen atom of the carbonyl
group. The coordination of the nitrogen of the hydrazine group is further sup-
ported by the shift of the (N–N) stretching vibrations in the complexes to
higher wave numbers by about 5–10 cm21, which were observed in the
1010–1030 cm21 region in the free ligands.[18]
The thioketo C55S stretching absorption bands observed in the region of
730–800 cm21 show no shift on complexation compared with the free ligand,
thus, the sulfur atom does not take part in bonding with metal ions. The thio-
amide bands observed in the regions 1545–1520, 1350–1340, 1080–1040,

1764
Halli, Shashidhar, and Qureshi
and 720–800 cm21 are due to the amide I, II, III, and IV bands, respect-
ively.[19] The band IV having a major contribution from the C55S stretching
vibration shows no change in its position in the complexes suggesting the
non-participation of the sulfur atom in coordination.
The assignments of bands in the far-infrared region have been controver-
sial over the years, yet studies are useful as direct information about the
metal–ligand coordination bond are obtained. The non-ligand bands observed
in the regions 575–495 and 480–420 cm21 are assigned to n(M–N) and
n(M–O) stretching vibrations, respectively, in all of the complexes.[20] In
the case of polymeric complexes where both terminal and bridging metal
halogen linkages are present, the terminal M–Cl stretch occurs at the higher
wave number side than the bridging M–Cl stretching vibrations[21] In view
of this, we have assigned broad and weak-intensity, non-ligand bands
observed in, the regions 380–360 and 290–320 cm21 to n(M–Cl) terminal
and n(M–Cl) bridging vibrations, respectively, for the Co(II), Cu(II), Ni(II),
and Cd(II) complexes in view of their chloride bridged polymeric structures.
The bands in the region 320–360 cm21 are assigned to n(M–Cl) vibrations of
the Zn(II) and Hg(II) complexes (Fig. 2).
In the UO2(VI) and Th(IV) complexes the additional bands observed at
1030 and 1040 cm21 are assigned to n3 vibrations of the coordinated NO3
group.[22] The characteristic bands observed at 910 and 930 cm21, respec-
tively, indicate the linear character of the UO2 group.
Biological Activity
All the thiosemicarbazide ligands, complexes, and metal salts were tested
for their antimicrobial activity against the bacteria E. coli, Pseudomonas,
B. subtilus, and Wild bacillus by the cup–plate zone inhibition technique,[23]
at concentrations of 10 mg/mL in DMF solution. The standard used was gen-
tamycine sulfate 40 mg/mL and the solvent control was also used to determine
the activity of the solvent. The Ni(II), Cd(II), and Hg(II) complexes of
BCMePT are more active against all the bacteria compared with the metal
salts and ligands, whereas the UO2(VI) and Th(IV) complexes are more
active against Wild bacillus only. In the case of BCMeOPT, the Hg(II) and
UO2(VI) complexes are moderately active towards Wild bacillus. The
Co(II), Ni(II), Cu(II), Zn(II), and Cd(II) complexes of BCBrPT are moderately
active against Wild bacillus and the Ni(II) and Hg(II) complexes are moder-
ately active against Pseudomonas and E. coli bacteria, respectively. All the
ligands and the other metal complexes are inactive against all the bacteria
tested. The Ni(II), Cd(II), and Hg(II) complexes of BCMePT are almost as

Metal Complexes of Benzofuran Thiosemicarbazides
1765
Figure 2. Suggested structures of the complexes.
active as the standard gentamycine sulfate. These preliminary results show
that the activity of the ligands has been enhanced when it is applied in the
form of metal complexes.
CONCLUSION
On the basis of elemental analyses, magnetic moments, conductance data,
IR, and electronic spectral studies and the high melting points and insolubility
in common organic solvents, we tentatively propose chloride bridged
polymeric octahedral structures for the Co(II), Cu(II), Ni(II), and Cd(II) com-
plexes whereas monomeric tetrahedral structures are suggested for Zn(II) and
Hg(II) complexes. A diameric octahedral structure is suggested for the

1766
Halli, Shashidhar, and Qureshi
Scheme 1.
UO2(VI) complexes and ligand bridged polymeric six coordination is assigned
to the Th(IV) complexes.
ACKNOWLEDGMENTS
One of the authors (MBH) is thankful to the University Grants Commis-
sion (UGC), New Delhi, for financial assistance in form of a Major Research
Project and ZSQ is thankful to the UGC, New Delhi, for awarding a teacher

Metal Complexes of Benzofuran Thiosemicarbazides
1767
fellowship under the IX plan period. We thank the Professor and Chairman,
Department of Chemistry, Gulbarga University, Gulbarga, for encouragement
and for the use of their facilities.
REFERENCES
1. Dey, K.; Bandyopandhyay, D. Transition metal complexes of thioderiva-
tives of hydrazones. J. Indian Counc. Chem. 1999, 16 (1), 36–62.
2. Bhamaria, R.P.; Bellare, R.A.; Deliwala, C.V. In vitro effect of 1-acyl-4-
alkyl-(or aryl)-thiosemicarbazides, 1-(5-chlorosalicylidine)-4-alkyl-(or
aryl)-thiosemicarbazones and some hydrazones of 5-chlorosalicylalde-
hyde against pathogenic bacteria including mycobacterium tuberculosis
(H37Rv). Indian J. Exp. Biol. 1968, 6, 62–63.
3. Dwyer, F.P.; Mellor, D.P. Chelating Agents and Metal Chelates; Aca-
demic Press: London, 1964.
4. Frear, D.E.H. Chemistry of Pesticides; Van Nostrand: New York, 1955;
295.
5. Mason, J.W. Drug therapy. New. Eng. J. Med. 1987, 316, 455–466.
6. Vogel, A.I. A Text Book of Quantitative Inorganic Analysis, 3rd Ed.;
Longman: London, 1968.
7. Halli, M.B.; Hiremath, A.C.; Huggi, N.V. Synthesis and characterization
of cobalt(II), nickel(II), copper(II), zinc(II) and cadmium(II) complexes
with 3-acetylamino-2-benzoylbenzofuran. Indian J. Chem. 2001, 40A,
645–647.
8. Geary, W.J. The use of conductivity measurements in organic solvents for
the characterization of coordination compounds. Coord. Chem. Rev.
1971, 7, 81–122.
9. Lever, A.B.P. Inorganic Electronic Spectroscopy; Elsevier: Amsterdam,
1968; 341–344.
10. Parihari, R.K.; Patel, R.K.; Patel, R.N. Synthesis and characterization
of metal complexes of manganese(II), cobalt(II) and zinc(II) with
Schiff base and some neutral ligands. J. Indian Chem. Soc. 2000, 77,
339–340.
11. Naik, N.; Purohit, K.M.; Patel, R.N. Studies on mixed-ligand complexes
of copper(II), nickel(II) and cobalt(II) with some Schiff base and
dimethylglyoxime. J. Indian Counc. Chem. 1998, 15, 7–9.
12. Underhill, A.E.; Billing, D.E. Calculation of Racah parameter B for
nickel(II) and cobalt(II) compounds. Nature 1966, 210, 834–835.
13. Cotton, F.A.; Wilkinson, G. Advanced Inorganic Chemistry, 2nd Ed.;
Wiley Pvt. Ltd.: New Delhi, 1967.

1768
Halli, Shashidhar, and Qureshi
14. El-Asmy, A.A.; Buhket, M.M.; Ibrahim, K.M.; Mostafa, M.M. Synthesis
and structural studies on 4-phenyl-l-hippuroyl-3-thiosemicarbazide
(DHP) complexes with some divalent metal ions. Synth. React. Inorg.
Met.-Org. Chem. 1986, 16 (10), 1453–1462.
15. Khana, D.; Banerjee, V.; Agarwala, B.V.; Dey, A.K. Coordination poly-
mers of cobalt(II), nickel(II), copper(II), zinc(II) and cadmium(II) with
1-isoniconoyl-4-allyl-3-thiosemicarbazide. Indian J. Chem. 1982, 21A,
621–624.
16. Nikolaev, A.V.; Lagvievnko, V.A.; Maychina, L.I. Thermal Analysis;
Academic Press: New York, 1969; Vol. 2, 779.
17. Biradar, N.S.; Patil, B.R.; Kulkarni, V.H. Kupfer(II)-Komplexe mit 2,20-
dihydroxychalkonen. Monatsh. Chem. 1976, 107, 251–257.
18. Singh, N.K.; Agawala, N.R. Synthesis and spectroscopic studies of cobalt (II),
nickel(II), copper(II) and zinc(II) complexes of pyridine-2-carboxaldehyde
thiobenzoylhydrazone. Indian J. Chem. 1998, 37A, 276–279.
19. Singh, C.; Parwana, H.K.; Singh, G.; Jolly, R.S. Metal complexes of pyri-
dine-3-carboxylaldehyde Thiosemicarbazone. Asian J. Chem. 2000,
12 (1), 1–8.
20. Ferror, J.R. Low Frequency Vibrations of Inorganic and Coordination
Compounds; Plenum: New York, 1971; 90.
21. Hiremath, A.C.; Reddy, K.M.; Patel, K.M.; Halli, M.B. Metal complexes
of Schiff bases derived from 4-hydrazinbenzofuro[3,2-d]pyridimine and
benzaldehydes. Proc. Natl. Acad. Sci. India. 1993, 63 (A)II, 341–345.
22. Ahuja, I.A.; Singh, R. 1,3-D-(4-pyridyl)propane complexes with some
uranyl salts. J. Inorg. Nucl. Chem. Lett. 1976, 12 (9), 655–670; Chem.
Abstr. 1976, 85, 153287d.
23. Collins, C.H.; Lyne, P.M. Microbiological Methods, 4th Ed.; Butter-
worth: London, 1976, 235–240.
Received June 4, 2003
Accepted June 11, 2004