Synthesis, characterization and properties of nicotinamide and isonicotinamide complexes with diverse dicarboxylic acids

Arıcı, Mürsel; Yeşılel, Okan Zafer; Acar, E.; Dege, Necmi

doi:10.1016/j.poly.2017.02.013

Cited by 47 publications

(8 citation statements)

References 34 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“… As a result pincer-type complexes have been the focus of intense investigation over many years . There have been a wealth of derivatives featuring a diverse range of donor atoms including phosphorus, nitrogen, sulfur, oxygen, carbon, and others in various combinations. Despite the wide range, however, those pincers featuring boron-based motifs remain rare and are limited to a handful of examples (Figure ).…”

Section: Introductionmentioning

confidence: 99%

“…Despite the wide range, however, those pincers featuring boron-based motifs remain rare and are limited to a handful of examples (Figure ). ,− Furthermore, while there are many examples of pincer ligands where the central unit of the pincer ligand is a secondary group (i.e., where it contains a E–H group), ,,,,,,, there are only few examples featuring a secondary borane as the central unit. ,− We have a particular interest in transition-metal complexes containing boron-based ligands, specifically those containing borane functionalities where the boron acts as a Z-type ligand. , Indeed, several research groups are exploring the propensity of this functional group to act as an acceptor group for a hydrogen atom or other functional groups (Scheme ). The potential for groups to be stored at the boron center opens up the possibility for a mechanism of ligand cooperation in which the ligand is intimately involved in the transformations at the metal center as a means to facilitate catalytic transformations .…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Synthesis and Characterization of Platinum and Palladium Complexes Featuring a Rare Secondary Borane Pincer Motif

et al. 2018

View full text Add to dashboard Cite

The synthesis and characterization of a series of platinum and palladium complexes containing a secondary borane Z-class ligand supported by 2-mercaptopyridine heterocycles is reported herein. Addition of two equivalents of Na[H2B(mp)2] to [Pt(μ-Cl)(COE OMe)]2 (where COE OMe = 8methoxycyclooct-4-en-1-ide) in the presence of two equivalents of a tertiary phosphine {PR3 = PPh3, PCy3, PCyp3, P(o-tol)3, PPh2(o-tol) and PPh2(2-(3-methyl)indolyl)} leads to the formation of the complexes [Pt{κ 3-S,B,S-HB(mp)2}(PR3)] (1-6). Addition of two equivalents of Na[H2B(mp)2] to [Pd(μ-Cl)(COE OMe)]2 in the presence of two equivalents of a tertiary phosphine {PR3 = PPh3, PCy3, PCyp3, and PPh2(o-tol)} leads to the formation of the complexes [Pd{κ 3-S,B,S-HB(mp)2}(PR3)] (7-10). It was also demonstrated that the synthesis of the palladium complex 7 could be achieved from the palladium precursor, [PdCl(Me)(COD)] (where COD = 1,5cyclooctadiene) as an alternative synthetic strategy. In the above reactions, either the COE OMe 2 fragment or the methyl fragment serve to act as a "hydride acceptor" facilitating the ultimate transformation of the borohydride based ligand, [H2B(mp)2]to the corresponding secondary borane  3-S,B,S coordinated HB(mp)2 pincer ligand. The complexes [Pd{κ 3-S,B,S-HB(mp)2}(PR3)] and [Pt{κ 3-S,B,S-HB(mp)2}(PR3)] are rare examples of metal-borane complexes where one hydrogen substituent remains at the boron center. These compounds have particularly short palladium-and platinum-boron distances, the shortest of the structurally characterized compounds being 2.067(6) Å for [Pd{κ 3-S,B,S-HB(mp)2}(PPh2(o-tol))] and 2.076(10) Å, for [Pt{κ 3-S,B,S-HB(mp)2}(PCy3)], respectively (the shorter distances of two independent complexes in the unit cells of both structures).

show abstract

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of Platinum and Palladium Complexes Featuring a Rare Secondary Borane Pincer Motif

et al. 2018

View full text Add to dashboard Cite

show abstract

“…Besides, Isn formed numerous coordination complexes promoting their assembly in supramolecular structures mainly directed by the amide···amide pattern, even in competitive interactions with additional directing motifs [17,18,19,20]. In turn, carboxylates have a large versatility of coordination modes and can be used as a building block including Isn [21,22].…”

Section: Introductionmentioning

confidence: 99%

Isonicotinamide-Based Compounds: From Cocrystal to Polymer

et al. 2019

View full text Add to dashboard Cite

The reaction between [Cu(μ-OAc)(μ-Pip)(MeOH)]2 (1) (OAc = acetate; Pip = 1,3-benzodioxole-5-carboxylate) and isonicotinamide (Isn) in MeOH as solvent yielded two mixture pairs of three compounds: {(HPip)2(Isn) (2), [Cu(Pip)2(Isn)2] (3)} and {(3), {[Cu3(Pip)2(OAc)2(μ-Isn)2(Isn)2(μ-OCH3)2(MeOH)2]·2MeOH}n (4)}. Modifying the reaction conditions (t, T, molar ratio), 2 and 3 have been successfully isolated, whereas 3 and 4 had to be mechanically separated. The recrystallization of 3 in pentanol yielded single crystals of compound [Cu(Pip)2(Isn)2]·C5H11OH (3a). The X-ray crystal structure of 2, 3a, and 4 has been elucidated showing a cocrystal, a monomer, and an unusual coordination polymer, respectively. The Pip ligand exhibited a chelate (3a) or a monodentate (4) coordination mode, but the Isonicotinamide (Isn) ligand is the one that promoted the arrangement of different structures and also mainly directs the formation of the 2D and 3D supramolecular assemblies. All the structures have been analyzed by Hirshfeld surface. In addition, the energy frameworks and lattice energy values of 2 and 3a have been calculated.

show abstract

“…The isonicotinamide and pyrazine, which are used as co-formers in the formation of the co-crystals, have aromatic ring nitrogen atom that can form heterosynthon bonds with p-aminobenzoic acid. In addition, isonicotinamide is an antibacterial, antituberculosis compound capable of forming hydrogen bonds with oxygen and nitrogen atoms by means of potential donor atoms in amide group [20][21][22][23][24][25]. Pharmacological properties of pyrazine and its derivatives are also known.…”

mentioning

confidence: 99%

Synthesis and Characterization of Two New Co-Crystals: p-Aminobenzoic Acid with Isonicotinamide and Pyrazine (1:1)

Özbek

2019

Hittite J. Sci. Eng.

View full text Add to dashboard Cite

C o-crystals are made up of two or more molecular or ionic compounds combining at a cytochiometric rate, having a different crystallographic pattern than the precursor compounds, and being two or multi-component molecular crystals [1-3]. Molecules forming them are connected to each other by intermolecular interactions such as hydrogen bonds, π-π stacking interactions, C-H…π and Van der Waals forces [4,5]. The most preferred methods used in the preparation of the co-crystals are precipitation, slurry formation, cooling crystallization, grinding, as well as the evaporation that is the most common method. These methods can be applied differently within themselves [6-10]. Co-crystals have been widely used in the field of pharmacology, cosmetics, agriculture, paint, food, optoelectronic and photonic device industries in recent years. A co-crystal usually has some different properties than its constituent compounds, such as resolution, crystallization, melting point, optical properties, biocompatibility and thermodynamic stability [4, 11-14]. In previous studies, two new co-crystals composed of benzoic acid derivatives and pyridine derivatives have been reported. Many different biological activities of these organic ligands and their metal complexes have been investigated, and these complexes have been proven to be more biologically active compounds than free ligands. This phenomenon is not only for metal complexes but

show abstract

Synthesis, characterization and properties of nicotinamide and isonicotinamide complexes with diverse dicarboxylic acids

Cited by 47 publications

References 34 publications

Synthesis and Characterization of Platinum and Palladium Complexes Featuring a Rare Secondary Borane Pincer Motif

Synthesis and Characterization of Platinum and Palladium Complexes Featuring a Rare Secondary Borane Pincer Motif

Isonicotinamide-Based Compounds: From Cocrystal to Polymer

Synthesis and Characterization of Two New Co-Crystals: p-Aminobenzoic Acid with Isonicotinamide and Pyrazine (1:1)

Contact Info

Product

Resources

About