Structure of salicylaldehyde thiosemicarbazone

Chattopadhyay, D.; Μazumdar, S. Κ.; Banerjee, T.; Ghosh, S.; Mak, Thomas C. W.

doi:10.1107/s010827018800040x

Cited by 42 publications

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“…This paves the way for the moiety to attain the stable conformation The negative charge on the atom N22 increases while that in N19 decreases, a common feature observed in TSC moieties [22]. Owing to the swelling of the electron cloud around the N22 atom, the metal complexation or the reduction process may not be feasible [23].…”

Section: Resultsmentioning

confidence: 99%

Crystal structure and conformation study of N‐methyl‐t‐3‐methyl‐r‐2, c‐6‐diphenylpiperidin‐4‐one thiosemicarbazone

Natarajan

Ponnuswamy

Nethaji

2006

Cryst. Res. Technol.

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Section: Resultsmentioning

confidence: 99%

Crystal structure and conformation study of N‐methyl‐t‐3‐methyl‐r‐2, c‐6‐diphenylpiperidin‐4‐one thiosemicarbazone

Natarajan

Ponnuswamy

Nethaji

2006

Cryst. Res. Technol.

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“…All of the structural features of SASC are similar to those of the previously reported structure. The carbonyl group is in the anti conformation with respect to N7, a conformation observed in similar compounds (Soriano-Garcfa, Vald6s-Martfnez & Toscano, 1988;Chattopadhyay, Mazumdar, Banerjee, Ghosh & Mak, 1988;Soriano-Garcfa, Vald6s-Martinez, Toscano, Gomez-Lara & Villalobos-Penalosa, 1986;Naik & Palenik, 1974;Nardelli, Fava & Giraldi, 1965). Bond lengths and angles of the C1-C8 chain suggest 7r-electron delocalization along the chain.…”

Section: Commentmentioning

confidence: 87%

Salicylaldehyde Semicarbazone–Acetic Acid Hydrogen-Bonded Complex

Abboud¹,

Summers²,

Palenik³

1995

Acta Crystallogr C

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The crystals of CsH9N302.C2H402 consist of a one-toone ratio of salicylaldehyde semicarbazone and acetic acid. Each molecule of salicylaldehyde semicarbazone is joined to an acetic acid molecule by a double hydrogen bond. This arrangement is very similar to the typical carboxylic acid dimer. The crystal structure exhibits a three-dimensional network of hydrogen bonds involving all of the possible hydrogen-bond donors and acceptors in both molecules. A displacement-ellipsoid drawing (SHELXTL-Plus; Sheldrick, 1991) of the molecules with the atomlabelling scheme is presented in Fig. 1. The structure of SASC has been determined previously (Vald6s-Martfnez, Toscano, Salcedo, Cea-Olivares & Mel6ndez, 1990). We report the crystal structure of the title compound SASC-HAc, crystallized in a 1:1 ratio. All of the structural features of SASC are similar to those of the previously reported structure. The carbonyl group is in the anti conformation with respect to N7, a conformation observed in similar compounds (Soriano-Garcfa, Vald6s-Martfnez & Toscano, 1988;Chattopadhyay, Mazumdar, Banerjee, Ghosh & Mak, 1988; Soriano-Garcfa, Vald6s-Martinez, Toscano, Gomez-Lara & Villalobos-Penalosa, 1986;Naik & Palenik, 1974;Nardelli, Fava & Giraldi, 1965). Bond lengths and angles of the C1-C8 chain suggest 7r-electron delocalization along the chain. This delocalization is also supported by the torsion angles along the chain: C2----C1---C7--N7 = -2.3 (4), C1---C7--N7--N8 = -179.5 (3), C7--N7--N8---C8 = 172.0 (2), N7--N8---C8~N8b = 7.4(4) and N7--N8---C8---O8a = -172.1 (2) °. The least-squares plane of the semicar-bazone moiety forms an angle of 5 ° with the plane of the phenyl ring.Fig. 1. Molecular structure with 50% probability ellipsoids, showing the atom-numbering scheme.The presence of acetic acid in the crystal provides an extensive network of three-dimensional hydrogen bonding. H2 and H8b are involved in intermolecular hydrogen bonds with O9a, and intramolecular hydrogen bonds with N7. These intramolecular hydrogen bonds seem to be strong enough to prevent metal complex formation. Evidently, the presence of H2 and H8b and their interactions with the lone pair of electrons on N7 render these electrons inaccessible to the metal ions. There are three moieties in the structure that have both donor and acceptor sites, i.e. H8--N8-----C8---O8a, H8a--N8b---C8--O8a and H9b---O9b---C9-----O9a. Interactions among these groups provide the strongest hydrogen bonds in this structure. One of these interactions involves the H8--N8---C8---O8a moiety where molecules of SASC form cyclic dimers around crystallographic centers of inversion. Experimental 02All materials used, including salicylaldehyde, semicarbazide 08a N8b hydrochloride, sodium acetate, bismuth subcarbonate and O9a glacial acetic acid, were obtained commercially and used with-O9b out further purification. The SASC ligand was synthesized N7 by adding 0.94 ml of salicylaldehyde to a solution of ap-N8 C1 proximately 1 g of semicarbazide hydrochloride and 1.5 g of c2 sodium ace...

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“…32 The bands near 340 nm for complexes (IV-V) are due to S(σ, π) → M(II) charge transfer bands. 13 The thermal behavior of the reported complexes was investigated using T.G. technique and the resulting data are given in Table 3 , 0.424 mg) shows the first weight loss endotherm between 287-380 o C which may be attributed to the release of two NH 2 CSN fragments 33 (found 28%, calcd 27.7%).…”

Section: Resultsmentioning

confidence: 99%

“…11 However, incorporation of a third donor site (D) into these thiosemicarbazone ligands linked to the carbonylic carbon via one or two intervening atoms usually results in D,N,S tricoordination 11 as shown in (I). Though, the thiosemicarbazone moiety of the free tridentate ligand (I) exists in the thione form, 13 it is known to bind as a dianionic tridentate D,N,S donors.…”

Section: Introductionmentioning

confidence: 99%

Copper(II), Nickel(II) and Palladium(II) Complexes of 2-Oximino-3-thiosemicarbazone-2,3-butanedione

2004

Bulletin of the Korean Chemical Society

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A new tridentate ligand incorporating a monoxime and thiosemi-carbozone moieties has been synthesized. Its copper(II), nickel(II) and palladium(II) complexes have been prepared and characteirzed by physical and spectral methods. Elemental analyses and spectroscopic data of the metal complexes are consistent with the formation of a mononuclear copper(II) complex and binuclear complex with both nickel(II) and palladium(II). In the copper(II) complex the fourth coordination site is occupied by nitrate ion. In the binculear complexes the fourth coordination site is occupied by the deprotonated oxime oxygen of the ligand coordinated to the other metal.

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Structure of salicylaldehyde thiosemicarbazone

Cited by 42 publications

References 0 publications

Crystal structure and conformation study of N‐methyl‐t‐3‐methyl‐r‐2, c‐6‐diphenylpiperidin‐4‐one thiosemicarbazone

Crystal structure and conformation study of N‐methyl‐t‐3‐methyl‐r‐2, c‐6‐diphenylpiperidin‐4‐one thiosemicarbazone

Salicylaldehyde Semicarbazone–Acetic Acid Hydrogen-Bonded Complex

Copper(II), Nickel(II) and Palladium(II) Complexes of 2-Oximino-3-thiosemicarbazone-2,3-butanedione

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