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Transition metal complexes of an isatinic quinolyl hydrazone

Seleem HS - Chem Cent J (2011)

Bottom Line: The effect of the type of the metal ion for the same anion (Cl-) is obvious from either structural diversity of the isolated complexes (Oh, Td and D4h) or the various modes of bonding.The isatinic hydrazone uses its lactim form in all complexes (Cl-) except complex 5 (SO42-) in which it uses its lactam form.Also, the antimicrobial activity is highly influenced by the nature of the metal ion and the order for S. aureus bacteria is as follows: Nickel(II) > Vanadyl(II) > Cobalt(II) > Copper(II) ≈ Palladium(II) > Iron(III).

Affiliation: Ain Shams University, Faculty of Education, Department of Chemistry, Roxy, Cairo, Egypt. hsseleem@yahoo.com.

ABSTRACT

Background: The importance of the isatinic quinolyl hydrazones arises from incorporating the quinoline ring with the indole ring in the same compound. Quinoline ring has therapeutic and biological activities. On the other hand, isatin (1H-indole-2,3-dione) and its derivatives exhibit a wide range of biological activities. Also, the indole ring occurs in Jasmine flowers and Orange blossoms. Recently, the physiological and biological activities of quinolyl hydrazones arise from their tendency to form metal chelates with transition metal ions. In this context, we have reported to isolate, characterize and study the biological activity of some transition metal complexes of an isatinic quinolyl hydrazone; 3-[2-(4-methyl quinolin-2-yl)hydrazono] indolin-2-one.

Results: Mono- and binuclear as well as dimeric chelates were obtained from the reaction of a new isatinic quinolyl hydrazone with Fe(III), Co(II), Ni(II), Cu(II), VO(II) and Pd(II) ions. The ligand showed a variety of modes of bonding viz. (NNO)2-, (NO)- and (NO) per each metal ion supporting its ambidentate and flexidentate characters. The mode of bonding and basicity of the ligand depend mainly on the type of the metal cation and its counter anion. All the obtained Pd(II)- complexes have the preferable square planar geometry (D4h- symmetry) and depend mainly on the mole ratio (M:L).

Conclusion: The effect of the type of the metal ion for the same anion (Cl-) is obvious from either structural diversity of the isolated complexes (Oh, Td and D4h) or the various modes of bonding. The isatinic hydrazone uses its lactim form in all complexes (Cl-) except complex 5 (SO42-) in which it uses its lactam form. The obtained Pd(II)- complexes (dimeric, mono- and binuclear) are affected by the mole ratio (M:L) and have the square planar (D4h) geometry. Also, the antimicrobial activity is highly influenced by the nature of the metal ion and the order for S. aureus bacteria is as follows: Nickel(II) > Vanadyl(II) > Cobalt(II) > Copper(II) ≈ Palladium(II) > Iron(III).

Mass fragmentation pattern of the isatinic hydrazone.
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C2: Mass fragmentation pattern of the isatinic hydrazone.

Mentions: The results of elemental analysis of the investigated hydrazone (H2L; Scheme 1) are in good agreement with the proposed molecular formula; C18H14N4O (302.36): Calcd.: C, 71.50; H, 4.68; N, 18.53 Found: C, 71.40; H, 4.50; N, 18.60. The IR spectrum showed very strong bands at 3333, 1684 and 1633 cm-1 assignable to ν(NH), ν(C = O) and ν(C = N), respectively, confirming the lactam nature of H2L. Also, the 1H NMR spectral data of the ligand in d6-DMSO relative to TMS (Figure 1) provide a further support of the lactam nature of the hydrazone. The mass spectrum of the ligand showed the M+ peak at m/z = 302 and the base peak at m/z = 273 confirming its formula weight. Furthermore, the mass fragmentation pattern (Scheme 2) supported the suggested structure of the ligand.

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Transition metal complexes of an isatinic quinolyl hydrazone

Seleem HS - Chem Cent J (2011)

Mass fragmentation pattern of the isatinic hydrazone.
© Copyright Policy
C2: Mass fragmentation pattern of the isatinic hydrazone.
Mentions: The results of elemental analysis of the investigated hydrazone (H2L; Scheme 1) are in good agreement with the proposed molecular formula; C18H14N4O (302.36): Calcd.: C, 71.50; H, 4.68; N, 18.53 Found: C, 71.40; H, 4.50; N, 18.60. The IR spectrum showed very strong bands at 3333, 1684 and 1633 cm-1 assignable to ν(NH), ν(C = O) and ν(C = N), respectively, confirming the lactam nature of H2L. Also, the 1H NMR spectral data of the ligand in d6-DMSO relative to TMS (Figure 1) provide a further support of the lactam nature of the hydrazone. The mass spectrum of the ligand showed the M+ peak at m/z = 302 and the base peak at m/z = 273 confirming its formula weight. Furthermore, the mass fragmentation pattern (Scheme 2) supported the suggested structure of the ligand.

Bottom Line: The effect of the type of the metal ion for the same anion (Cl-) is obvious from either structural diversity of the isolated complexes (Oh, Td and D4h) or the various modes of bonding.The isatinic hydrazone uses its lactim form in all complexes (Cl-) except complex 5 (SO42-) in which it uses its lactam form.Also, the antimicrobial activity is highly influenced by the nature of the metal ion and the order for S. aureus bacteria is as follows: Nickel(II) > Vanadyl(II) > Cobalt(II) > Copper(II) ≈ Palladium(II) > Iron(III).

Affiliation: Ain Shams University, Faculty of Education, Department of Chemistry, Roxy, Cairo, Egypt. hsseleem@yahoo.com.

ABSTRACT

Background: The importance of the isatinic quinolyl hydrazones arises from incorporating the quinoline ring with the indole ring in the same compound. Quinoline ring has therapeutic and biological activities. On the other hand, isatin (1H-indole-2,3-dione) and its derivatives exhibit a wide range of biological activities. Also, the indole ring occurs in Jasmine flowers and Orange blossoms. Recently, the physiological and biological activities of quinolyl hydrazones arise from their tendency to form metal chelates with transition metal ions. In this context, we have reported to isolate, characterize and study the biological activity of some transition metal complexes of an isatinic quinolyl hydrazone; 3-[2-(4-methyl quinolin-2-yl)hydrazono] indolin-2-one.

Results: Mono- and binuclear as well as dimeric chelates were obtained from the reaction of a new isatinic quinolyl hydrazone with Fe(III), Co(II), Ni(II), Cu(II), VO(II) and Pd(II) ions. The ligand showed a variety of modes of bonding viz. (NNO)2-, (NO)- and (NO) per each metal ion supporting its ambidentate and flexidentate characters. The mode of bonding and basicity of the ligand depend mainly on the type of the metal cation and its counter anion. All the obtained Pd(II)- complexes have the preferable square planar geometry (D4h- symmetry) and depend mainly on the mole ratio (M:L).

Conclusion: The effect of the type of the metal ion for the same anion (Cl-) is obvious from either structural diversity of the isolated complexes (Oh, Td and D4h) or the various modes of bonding. The isatinic hydrazone uses its lactim form in all complexes (Cl-) except complex 5 (SO42-) in which it uses its lactam form. The obtained Pd(II)- complexes (dimeric, mono- and binuclear) are affected by the mole ratio (M:L) and have the square planar (D4h) geometry. Also, the antimicrobial activity is highly influenced by the nature of the metal ion and the order for S. aureus bacteria is as follows: Nickel(II) > Vanadyl(II) > Cobalt(II) > Copper(II) ≈ Palladium(II) > Iron(III).

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