Synthesis of tungsten compounds with Schiff base ligands prepared from ferrocenecarboxaldehyde: Observation of the migration of an imine double bond

Herrick, Richard S.; Ziegler, Christopher J.; Precopio, Melissa; Crandall, Kerianne; Shaw, Janet L.; Jarret, Ronald M.

doi:10.1016/j.jorganchem.2007.11.046

Cited by 14 publications

(9 citation statements)

References 16 publications

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“…For background to the synthesis of Schiff base compounds, see: Herrick et al (2008); Suresh et al (2007). For the biological activity of Schiff base compounds, see: Bhandari et al (2008); Sinha et al (2008).…”

Section: Related Literaturementioning

confidence: 99%

(E)-N′-(5-Chloro-2-hydroxybenzylidene)-3,5-dihydroxybenzohydrazide monohydrate

et al. 2009

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In the title compound, C14H11ClN2O4·H2O, the dihedral angle between the two benzene rings is 8.5 (2)° and an intramolecular O—H⋯N hydrogen bond is observed in the Schiff base molecule. In the crystal structure, the water molecule accepts an N—H⋯O hydrogen bond and makes O—H⋯O hydrogen bonds to two further Schiff base molecules. Further intermolecular O—H⋯O hydrogen bonds lead to the formation of layers parallel to the bc plane.

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Section: Related Literaturementioning

confidence: 99%

(E)-N′-(5-Chloro-2-hydroxybenzylidene)-3,5-dihydroxybenzohydrazide monohydrate

et al. 2009

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“…For the synthesis of Schiff base compounds, see: Herrick et al (2008); Suresh et al (2007); Liu et al (2007). For the background on biological activities, see: Bhandari et al (2008); Sinha et al (2008); Sun et al (2008).…”

Section: Related Literaturementioning

confidence: 99%

“…Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97. Schiff base compounds can be easily synthesized from the reaction of aldehydes with primary amines (Herrick et al, 2008;Suresh et al, 2007;Liu et al, 2007). These compounds show interesting biological activities, especially antimicrobial activities (Bhandari et al, 2008;Sinha et al, 2008;Sun et al, 2008).…”

Section: Data Collectionmentioning

confidence: 99%

N′-(3,5-Dichloro-2-hydroxybenzylidene)-3-methoxybenzohydrazide methanol solvate

et al. 2008

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“…The unusually long C(O)-N bond demonstrates that the aromaticity of the pyrazole ring prevents resonance stabilization of this bond. The C@O bond shows little change in length; the resonance of the carbonyl carbon in 13 (6) 1.198 (6) 1.462 (6) a All distances are in Å. Table 1 for bond distance comparison with 1.…”

Section: Discussionmentioning

confidence: 99%

“…Crystal structures of the two compounds show that the imine double bond formed from the 2-(aminomethyl)pyridine has migrated so that it is conjugated with the pyridine ring forming W(CO) 4 (g 2 -NC 5 H 4 CH@NCH 2 C 5 H 4 FeCp). In contrast, the imine double bond created with 2-(2-aminoethyl)pyridine remains conjugated with the cyclopentadienyl ring, forming W(CO) 4 (g 2 -NC 5 H 4 C 2 H 4 N@CHC 5 H 4 FeCp) [13].…”

Section: Introductionmentioning

confidence: 99%