Diorganotin(IV) derivatives of N-methyl p-fluorobenzo-hydroxamic acid

Preparation, spectral characterization, X-ray diffraction studies and antitumor activity

Naqeebullah, Yang Farina Abdul Aziz, Chan Kok Meng, Lo Kong Mun, Nor Fadilah Rajab, Theng Choon Ooi

Research output: Contribution to journalArticle

16 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)8696-8711
Number of pages16
JournalMolecules
Volume18
Issue number7
DOIs
Publication statusPublished - Jul 2013

Fingerprint

Hydroxamic Acids
X-Ray Diffraction
Ligands
Derivatives
X ray diffraction
preparation
ligands
acids
Tin
diffraction
tin
x rays
Crystal structure
crystal structure
Sodium Bicarbonate
Acids
hydrochlorides
Toluene
separators
Separators

Keywords

  • Antitumor activity
  • Hydroxamic acid
  • Organotin
  • X-ray diffraction

ASJC Scopus subject areas

  • Organic Chemistry
  • Medicine(all)

Cite this

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title = "Diorganotin(IV) derivatives of N-methyl p-fluorobenzo-hydroxamic acid: Preparation, spectral characterization, X-ray diffraction studies and antitumor activity",
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 = "Antitumor activity, Hydroxamic acid, Organotin, X-ray diffraction",
author = "Naqeebullah and {Abdul Aziz}, {Yang Farina} and {Kok Meng}, Chan and Mun, {Lo Kong} and Rajab, {Nor Fadilah} and Ooi, {Theng Choon}",
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T1 - Diorganotin(IV) derivatives of N-methyl p-fluorobenzo-hydroxamic acid

T2 - Preparation, spectral characterization, X-ray diffraction studies and antitumor activity

AU - Naqeebullah,

AU - Abdul Aziz, Yang Farina

AU - Kok Meng, Chan

AU - Mun, Lo Kong

AU - Rajab, Nor Fadilah

AU - Ooi, Theng Choon

PY - 2013/7

Y1 - 2013/7

N2 - 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.

AB - 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.

KW - Antitumor activity

KW - Hydroxamic acid

KW - Organotin

KW - X-ray diffraction

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