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Molecules 2013, 18(7), 8696-8711; doi:10.3390/molecules18078696
Article

Diorganotin(IV) Derivatives of N-Methyl p-Fluorobenzo-Hydroxamic Acid: Preparation, Spectral Characterization, X-ray Diffraction Studies and Antitumor Activity

1,2, 1,* , 3, 4, 5 and 5
1 School of Chemical Sciences and Food Technology, Faculty of Science & Technology, Universiti Kebangsaan Malaysia, 43600 Bangi, Selangor Darul Ehsan, Malaysia 2 Department of Chemistry, Faculty of Basic Sciences, University of Balochistan, 87300 Sariab Road Quetta, Pakistan 3 Environmental Health Programme, Faculty of Allied Health Sciences, Universiti Kebangsaan Malaysia, Jalan Raja Muda Abdul Aziz, 50300 Kuala Lumpur, Malaysia 4 Department of Chemistry, Faculty of Science, University of Malaya, 50603 Kuala Lumpur, Malaysia 5 Biomedical Science Programme, Faculty of Health Sciences, Universiti Kebangsaan Malaysia, Jalan Raja Muda Abdul Aziz, 50300 Kuala Lumpur, Malaysia
* Author to whom correspondence should be addressed.
Received: 23 May 2013 / Revised: 15 July 2013 / Accepted: 16 July 2013 / Published: 22 July 2013
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Abstract

Three diorganotin(IV) complexes of the general formula R2Sn[RcC(O)N(RN)O] (Rc = aryl, RN = Alkyl) have been synthesized by refluxing in toluene the corresponding diorganotin(IV) oxides with the free ligand N-methyl p-fluorobenzohydroxamic acid, using a Dean and Stark water separator. The ligand was derived from the reaction of the corresponding p-fluorobenzoyl chloride and N-methylhydroxylamine hydrochloride in the presence of sodium hydrogen carbonate. The isolated free ligand and its respective diorganotin compounds have been characterized by elemental analysis, IR and 1H-, 13C-, 119Sn-NMR spectroscopies. The crystal structures of the diorganotin complexes have been confirmed by single crystal X-ray diffraction methods. The investigations carried out on the diorganotin(IV) complexes of N-methyl p-fluorobenzohydroxamic acid confirmed a 1:2 stoichiometry. The complex formation took place through the O,O-coordination via the carbonyl oxygen and subsequent deprotonated hydroxyl group to the tin atom. The crystal structures of three diorganotin complexes were determined and were found to adopt six coordination geometries at the tin centre with coordination to two ligand moieties.
Keywords: organotin; hydroxamic acid; X-ray diffraction; antitumor activity organotin; hydroxamic acid; X-ray diffraction; antitumor activity
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

Naqeebullah; Farina, Y.; Chan, K.M.; Mun, L.K.; Rajab, N.F.; Ooi, T.C. Diorganotin(IV) Derivatives of N-Methyl p-Fluorobenzo-Hydroxamic Acid: Preparation, Spectral Characterization, X-ray Diffraction Studies and Antitumor Activity. Molecules 2013, 18, 8696-8711.

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