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.
Highlights
Hydroxamic acids [1], RcC(O)N(RN)OH (Rc = alkyl/aryl; RN = alkyl/aryl or H), have been the source of much biochemical interest in recent years reflecting the fact that they demonstrate a wide variety of biological activities
The structural and biological diversity of organotin hydroxamates stirred our interest to further illustrate the coordination chemistry and anti-proliferative activity of organotin compounds with hydroxamic acid, we report the synthesis of a new ligand N-methyl p-fluorobenzohydroxamic acid (LH) and its diorganotin(IV) derivatives (CH3)2SnL2, (C4H9)2SnL2 and (C6H5)2SnL2 with interesting structural features to expand their scope
Diorganotin(IV) complexes were synthesized in 2:1 molar ratio, by refluxing the free ligand with diorganotin(IV) oxides in hot toluene for 5–6 h with stirring and the water formed was removed azeotropically using a Dean-Stark apparatus (ii), as summarized in Scheme 1
Summary
Hydroxamic acids [1], RcC(O)N(RN)OH (Rc = alkyl/aryl; RN = alkyl/aryl or H), have been the source of much biochemical interest in recent years reflecting the fact that they demonstrate a wide variety of biological activities. Hydroxamic acids are capable of the inhibition of a variety of enzymes, including ureases [12,13], peroxidases [14], and matrix metalloproteinases (MMP) [15,16] and are capable of competing as siderophores for iron-(III) [17,18] These compounds are used in the design of therapeutics targeting cancer [19,20], cardiovascular diseases [21], HIV [22], Alzheimer’s [23], malaria [24,25], and allergic diseases [26]. The structural and biological diversity of organotin hydroxamates stirred our interest to further illustrate the coordination chemistry and anti-proliferative activity of organotin compounds with hydroxamic acid, we report the synthesis of a new ligand N-methyl p-fluorobenzohydroxamic acid (LH) and its diorganotin(IV) derivatives (CH3)2SnL2, (C4H9)2SnL2 and (C6H5)2SnL2 with interesting structural features to expand their scope
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