Synthesis characterization and antimicrobial activity of metal chelates of 1, 7-di (2-hydroxyphenyl) 1, 7 di (n-methyl) aza-1, 3, 5 heptarine-3-ol hydrochloride

Article abstract of DOI:10.1155/2010/587615

The Schiff base complexes derived from 2-furancarboxaldehyde and N-methyl-2-amino phenol have been prepared and characterized using several physical techniques, like elemental analysis, thermogravimetric analysis, magnetic moment measurements, infrared an

Full text of DOI:10.1155/2010/587615

ISSN: 0973-4945; CODEN ECJHAO
E-Journal of Chemistry
2010, 7(3), 775-778
http://www.e-journals.net
Synthesis Characterization and Antimicrobial
Activity of Metal Chelates of 1, 7-Di
(2-hydroxyphenyl) 1, 7 di (N-methyl) aza-1, 3, 5
heptarine-3-ol hydrochloride
NALIN P. PATANI* and M. V. HATHI
*C. U. Shah Science College, Ahmedabad-380014,Gujarat, India.
R. R. Mehta College of Science, Palanpur-385001, Gujarat, India.
nppatani@yahoo.co.in
Received 7 October 2009; Revised 17 December 2009; Accepted 10 February 2010
Abstract: The Schiff base complexes derived from 2-furancarboxaldehyde
and N-methyl-2-amino phenol have been prepared and characterized using
several physical techniques, like elemental analysis, thermogravimetric
analysis, magnetic moment measurements, infrared and resonance spectra.
N-Methyl-2-amino phenol was condensed stoichiometrically with 2-
furancarboxaldehyde in presence of methanol. The resulting 1,7-di(2-
hydroxyphenyl) 1,7 di(N-methyl) aza-1,3,5 heptarine-3-ol hydrochloride
was characterized by elemental analysis and spectral studies. The
transition metal complexes of Cu2+, Zn2+, Ni2+, Co2+ and Mn2+ of the
synthesized complexes were prepared. Metal ligand (M:L) ratio, IR,
reflectance spectral studies, magnetic properties and antimicrobial activity
of the synthesized complexes and its metal complexes were carried out.
Keywords: 2- Furancarboxaldehyde, N-Methyl-2-amino phenol, Metal complexes, Magnetic moment,
Antifungal activities.
Introduction
2- Furancarboxaldehyde is well known as an analytical reagent1,2. Its various derivatives3 are
also useful. The complexes obtained from ligands having methyl, ethyl, nitro as functional
group4 have been investigated exhaustively. Receiving impetus from the above observation
and continuation of our research program, it was thought to undertake such view. The
present communication describes the synthesis and characterization of 1,7-di(2-
hydroxyphenyl) 1,7 di(N-methyl)aza-1,3,5 heptarine-3-ol hydrochloride and its complexes

776
NALIN P. PATANI et al.
with Cu2+, Zn2+, Ni2+ and Co2+ also antimicrobial activities of these complexes. This work is
illustrated in Scheme 1.
OH
CHO
+
O
NH
CH3
Methyl-2-amino phenol
2-Furancarboxaldehyde
CH
3OH
conc.HCL
RT 5 days
HO
OH
+
N
N
Cl
OH
CH3
CH3
SSL-2
Scheme 1
Experimental
2-Amino phenol was obtained from local dealer in market. The metal salts and other chemicals
used were of analytical grade. To a solution of (0.1 M) N-methyl-2-amino phenol in methanol, a
solution of 2- furancarboxaldehyde (0.05 M) in methanol was added drop wise within 20
minutes. Then 9 mL conc. HCl was added slowly with maintaining the room temperature. The
mixture was kept aside for five days with occasional stirring. The resulting dark violet compound
was filtered and washed by methanol and then with ether5. Finally it was air-dried. The yield was
about 63%. The Cu2+, Zn2+, Ni2+ and Co2+ metal ion complexes of ligand SSL-2 were prepared
using the following procedure.
The solution of 25 mL disodium salt containing 0.01 M ligand was taken, then each ligand
was added drop wise to a solution of 0.005 M cupric nitrate hexahydrate in 100 of water with
rapid stirring. The pH of the resultant solution was 4.5. The solid mass was precipitated out. It
was allowed to settle down then digested on water bath at 70 ºC for about 2 h. The solid mass
was filtered, washed with 1:1 mixture of water-ethanol and finally with acetone and air-dried, the
resulting yield was 70%. The resulting complex was powdered well and further dried at 70 ºC
over a period of 24 h. The details of the elemental analysis of the complexes are given in Table 1.
Ligand 1,7-di(2-hydroxyphenyl)1,7 di (N-methyl)aza-1,3,5 heptarine-3- ol-hydrochloride (SSL-
2) and its synthesized complexes were insoluble in water, slightly soluble in methanol, ether,
chloroform and other organic solvents. They were soluble in DMF. All the samples were
measured by elemental analyzer Thermo Finiggan 1101 Flash EA6. IR spectra of SSL-2 and its
metal complexes were scanned on Nicolate 760 FTIR Spectrophotometer in KBr. The metal
content of the metal chelates by decomposing a weighed amount of each metal complexes were
analysed followed by EDTA titration as reported in literature7. Magnetic susceptibility
measurement of all metal complexes was carried out at room temperature by the Gouy method8
The values are given in Table 2. Mercury tetrathiocynatocobltate(II) was used as a calibrant9.The
reflectance spectra of the metal chelates in the visible region were recorded against MgO on
Backman DK 2A Spectrophotometer (Figure 1). The antimicrobial activities of the synthesized
metal complexes were carried out by cup-plate method10. All the samples were monitored against
various fungi following the method reported in literature11.

Synthesis Characterization and Antimicrobial Activity
777
1400
300
500
700
800
1100 1300
Wavenumber, nm
Figure 1. Reflectance spectra of SSL-2 metal complexes (1) SSL-2 Cu2+ (2) SSL-2 Ni2+ (3) SSL-2
Co2+ (4) SSL-2 Mn2+ .
Results and Discussion
1,7 Di(N-methyl)aza-1,3,5 heptarine-3-ol hydrochloride was dark violet powder. The result of
elemental analysis of ligand is reported in Table 1. The values are consistent with the predicted
structure (Scheme 1). The IR spectra of 1,7 di(N-methyl)aza-1,3,5 heptarine-3-ol hydrochloride
comprises the important bands12 observed at 3600 to 2600 cm-1. The IR spectra of all the chelates
suggest that the formation of entire metalocyclic compound by the absence of band
characteristic of free -OH group. The electronic spectrum of Co(II) complexes exhibits three
6
4
6
bands around 22834, 16462 and 9222 cm-1. Which are assigned A1g(F) → T2g(F), A1g(F) →
4T2g, 6A1g(F) → 4T2g(P) respectively in octahedral field13. The magnetic moment14 of the order is
3.76 B.M. The electronic spectra of Cu2+ metal chelate of each of the ligand may be assigned to
2B1g →2A1g and charge transfer transition respectively. The electronic spectral of Mn2+ complexes
were also show three bands. The examination of antifungal activity15 of SSL-2 ligands and its all
chelates (Table 3) indicates that all compounds are good toxic for fungi. Out of all the
compounds copper chelates is more than that of other (Table 3).
Table 1. Analytical data of the metal chelates of SSL - 2.
Elemental analysis
Metal, %
Molecular
formula
Yield Mol.
Wt.
C %
H %
N %
%
Cald. Found Cald. Found Cald. Found Cald. Found
C19 H20 N2 O4 Cu2+ 2H2O 65 439.5 51.8 51.6 4.6 4.5 6.4 6.3 14.4 14.3
C19 H20 N2 O4 Mn2+ 2H2O 67 431 52.9 52.7 4.6 4.5 6.5 6.4 12.7 12.6
C19 H20 N2 O4 Ni2+ 2H2O 57 435 52.4 52.3 4.6 4.5 6.4 6.3 13.5 13.4
C19 H20 N2 O4 Co2+ 2H2O 62 435 52.4 52.4 4.6 4.5 6.4 6.3 13.5 13.4
C19 H20 N2 O4 Zn2+ 2H2O 60 441 51.7 51.6 4.5 4.5 6.3 6.3 14.7 14.6

778
NALIN P. PATANI et al.
Table 2. Experimental data of magnetic moment of metal chelates of SSL- 2.
χg X106 χm X106
Theoretical
Metal
Complex
Observed Magnetic
moment µeff (B.M.) µeff=
(B.M.)
n+2)
(cgs)
(cgs)
n
(
(SSL-2) Cu2+
(SSL-2) Ni2+
(SSL-2)Co2+
(SSL-2) Mn2+
(SSL-2) Zn2+
2.55
7.42
13.39
33.84
-
1121.89
3230.72
5825.86
14588.76
-
1.65
2.80
3.76
5.95
-
1.73
2.82
3.87
5.91
D*
Table 3. Antifungal activity of SSL-2 and their metal complexes.
Zone of inhibition at 1000 ppm, %
Sample
Penicillium F.
Expansum Udum
Nigras Pora Trichoderma Erysiphe
Sp.
54
82
74
66
70
78
Sp.
62
88
68
74
69
45
pisi
65
75
75
66
66
64
SSL-2
54
88
62
75
66
54
55
78
70
70
54
58
(SSL-2)2 Cu2+
(SSL-2)2 Mn2+
(SSL-2)2 Zn2+
(SSL-2)2 Co2+
(SSL-2)2 Ni2+
Acknowledgment
The author is thankful to Ex. Principal Dr. M. V. Hathi, R. R. Mehta Science College,
Palanpur, Gujarat for providing me laboratory facility and Principal of C.U.Shah Science
College for encouragement in my research work.
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Bhakti, J Sci Ind Res., 1953, 114, 1213.
Poddar Z, Ana Chem., 1957, 154, 327.
Ullman`s Encyclopedia of Industrial Chem, Willey Veh., 1984, 26, 614.
Oster K A, and Golden M J, J Am Phrm Assoc., Sci Ed., 1947, 37, 283.
Vogel A I, book of practical organic Chemistry 5th Ed, Pearson education, New Delhi,
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Vogel A I, A Textbook of Quantative Analysis, 3rd Ed., ELBS, London, 1978.
Radjohn N and Sujatha G D, et al., Indian J Exp Biol., 1975, 13, 286.
Radjohn N, Org Synthesis, coll. Vol. IV Willey & Sons N.Y,1963
Lewis J and Wilkins R G, Modern Coordination Chemistry, Interscience, New York,1964.
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Baily W R and Scott E G, Diagnostic Microbiology, The C.V Moshy Cost.Lovis, 1966, 257.
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