Metal(II)-promoted hydrolysis of pyridine-2-carbonitrile to pyridine-2-carboxylic acid. The structure of [Cu(pyridine-2-carboxylate)2] · 2H2O

Segľa, Peter; Jamnický, M.; Koman, Marián; Šíma, Jozef; Głowiak, Tadeusz

doi:10.1016/s0277-5387(98)00259-9

Cited by 46 publications

(16 citation statements)

References 10 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The nature of the alcohol affects the identity of the product; reactions in MeOH lead to copper(II) picolinato complexes. [137][138][139]141] The temperature is also a particularly important synthetic parameter. If the reaction mixtures in EtOH or nPrOH are heated or refluxed, they yield exclusively copper(II) picolinato complexes.…”

Section: The X-co-co-x Family Of Ligands: An Unexplored Area In Coordmentioning

confidence: 99%

Adventures in the Coordination Chemistry of Di‐2‐pyridyl Ketone and Related Ligands: From High‐Spin Molecules and Single‐Molecule Magnets to Coordination Polymers, and from Structural Aesthetics to an Exciting New Reactivity Chemistry of Coordinated Ligands

et al. 2009

View full text Add to dashboard Cite

The coordination chemistry of di-2-pyridyl ketone and related ligands is reviewed. An outline of the variety of such ligands is presented. References are given to methods for the synthesis of ligands that are not available on the market. The activation of the carbonyl group(s) of some of the ligands towards further reactions seems to be an emergent area of synthetic inorganic chemistry. The coordination chemistry of each ligand with metals is briefly described. Emphasis is placed on structural features and physical properties (mainly magnetic) of the resulting metal clusters and coordination polymers. The structural diversity of the complexes stems from the ability of the deprotonated diol-or hemiketal-type Organization of This Microreview and General InformationThis Microreview presents a focused overview of the coordination chemistry of ligands with the general formulae X-CO-X, X-CO-Y, X-CO-CO-X, and X-CO-X-CO-X, where X and Y are donor groups. We mainly describe the polynuclear metal complexes (clusters) and coordination polymers that have derived from the use of these ligands and the organic chemistry of their metal complexes. From the viewpoint of properties, emphasis is placed on the magnetism of the metal complexes. Much of the chemistry, both published and unpublished, that is reported comes from our group; however, detailed reference to all appropriate work by others is provided. The Microreview aims not to be comprehensive in terms of a discussion of every known cluster or coordination polymer containing a ligand derived from the above-mentioned molecules; rather, it aims to provide [ ‡] ligands to adopt a variety of bridging coordination modes depending on the number of carbonyl groups, the nature of the extra donor groups in the molecule and on the reaction conditions. Employment of a second organic or inorganic ligand in this chemistry gives an extraordinary structural flexibility in the resulting mixed-ligand systems. The initial use of 1,1Ј-carbonyldiimidazole and 1,1Ј-oxalyldiimidazole in copper(II) chemistry, which leads to unprecedented coordination polymers containing alcoholysis and/or hydrolysis "fragments" of the ligands, is also illustrated.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009) the reader with some idea of the range of chemistry that has been carried out (and indeed remains still to do) with these ligands. The article contains eight sections, including this one. The next section is introductory: the reader can find brief, general information on the two classes of compounds that are frequently mentioned in this Microreview, namely metal clusters and polymers, as well as a short discussion of the organic chemistry of metal complexes, which is currently a popular topic in inorganic chemistry. The last part of Section 2 provides a "hors d'oeuvre" of the ligands that are discussed in detail in Sections 3-7. Section 8 provides initial conclusions and perspectives for future research. Sections 2 and 3 are divided into parts for clarity. The organization of this ...

show abstract

Section: The X-co-co-x Family Of Ligands: An Unexplored Area In Coordmentioning

confidence: 99%

Adventures in the Coordination Chemistry of Di‐2‐pyridyl Ketone and Related Ligands: From High‐Spin Molecules and Single‐Molecule Magnets to Coordination Polymers, and from Structural Aesthetics to an Exciting New Reactivity Chemistry of Coordinated Ligands

et al. 2009

View full text Add to dashboard Cite

show abstract

“…Nevertheless, the precisions of the Cu-N and both Cu-O bond lengths (0.002 Å ) obtained from our low-temperature study are significantly better than those obtained from room temperature data (0.01 Å ). The coordination polymer of complex 3 can be compared with other polymeric complexes of the general formula [Cu(l-RCO 2 ) 2 ] n ÁxH 2 O, where RCO 2 is picolinato and x = 0 [27,28]; or x = 2 [26,[29][30][31][32]; or l-RCO 2 -is isoquinoline-3-carboxylato and x = 4 [33]. Symmetry code: (i) -x, -y, -z Symmetry codes: (i) -x, -y, -z; (viii) -x ?…”

Section: Resultsmentioning

confidence: 99%

Synthesis, properties and crystal structures of nitrobenzoatocopper(II) complexes with pyrazinecarboxamide

Vasková

Padělková

Mazúr

et al. 2011

Transition Met Chem

View full text Add to dashboard Cite

The synthesis, spectral characterization and crystal structures of two nitrobenzoatocopper(II) complexes, namely [Cu(2-O 2 Nbz) 2 (pca) 2 (H 2 O) 2 ] (1) and [Cu(3, N) 2 bz) 2 (pca) 2 (H 2 O) 2 ] (2) (where 2-O 2 Nbz = 2-nitrobenzoate, 3,5-(O 2 N) 2 bz = 3,5-dinitrobenzoate, pca = pyrazinecarboxamide), are reported. Complexes 1 and 2 consist of centrosymmetric molecules with the Cu(II) atom monodentately coordinated by a pair of anionic 2-nitrobenzoato (1) or 3,5-dinitrobenzoato (2) ligands and a pair of pyrazinecarboxamide ligands, forming a nearly tetragonal basal plane, and by a pair of water ligands that complete the tetragonal-bipyramidal coordination polyhedron. The molecules of both complexes are linked by N-H_O and O-H_O hydrogen bonds and lie in planes, which have different orientations depending on the space group. Similar experiments with 3-nitrobenzoic acid resulted in the isolation of the hydrolysis product [Cu(pyzCOO) 2 ] n (3) (pyz-COO = pyrazinecarboxylate). The known crystal structure of complex 3 has been re-determined at low temperature with significantly higher precision. The crystal packing and C-H_O/C-H_N hydrogen bonds are discussed.

show abstract

“…The bond angles around atom Cu1 lie within the range 80± 100 , with the largest angle being O1 i ÐCu1ÐN1 of 99.26 (6) [symmetry code: (i) Àx, Ày, Àz]. The Cu1ÐO1 bond is shorter than other chemically similar CuÐO bond distances (1.94±1.98 A Ê ; Segl'a et al, 1998;Klein et al, 1982;Ptasiewicz-Ba Îk et al, 1995), e.g. in the mixed-valence Cu I /Cu II complex with pyrazine-2-carboxylic acid [1.941 (3) A Ê ; Liu et al, 2003].…”

Section: Commentmentioning

confidence: 99%

trans-Bis(dimethyl sulfoxide-κO)bis(3-oxo-3,4-dihydroquinoxaline-2-carboxylato-κ²N¹,O²)copper(II)

2007

View full text Add to dashboard Cite

The title compound, [Cu(C(9)H(5)N(2)O(3))(2)(C(2)H(6)OS)(2)], consists of octahedrally coordinated Cu(II) ions, with the 3-oxo-3,4-dihydroquinoxaline-2-carboxylate ligands acting in a bidentate manner [Cu-O = 1.9116 (14) A and Cu-N = 2.1191 (16) A] and a dimethyl sulfoxide (DMSO) molecule coordinated axially via the O atom [Cu-O = 2.336 (5) and 2.418 (7) A for the major and minor disorder components, respectively]. The whole DMSO molecule exhibits positional disorder [0.62 (1):0.38 (1)]. The octahedron around the Cu(II) atom, which lies on an inversion centre, is elongated in the axial direction, exhibiting a Jahn-Teller effect. The ligand exhibits tautomerization by H-atom transfer from the hydroxyl group at position 3 to the N atom at position 4 of the quinoxaline ring of the ligand. The complex molecules are linked through an intermolecular N-H...O hydrogen bond [N...O = 2.838 (2) A] formed between the quinoxaline NH group and a carboxylate O atom, and by a weak intermolecular C-H...O hydrogen bond [3.392 (11) A] formed between a carboxylate O atom and a methyl C atom of the DMSO ligand. There is a weak intramolecular C-H...O hydrogen bond [3.065 (3) A] formed between a benzene CH group and a carboxylate O atom.

show abstract

Metal(II)-promoted hydrolysis of pyridine-2-carbonitrile to pyridine-2-carboxylic acid. The structure of [Cu(pyridine-2-carboxylate)2] · 2H2O

Cited by 46 publications

References 10 publications

Adventures in the Coordination Chemistry of Di‐2‐pyridyl Ketone and Related Ligands: From High‐Spin Molecules and Single‐Molecule Magnets to Coordination Polymers, and from Structural Aesthetics to an Exciting New Reactivity Chemistry of Coordinated Ligands

Adventures in the Coordination Chemistry of Di‐2‐pyridyl Ketone and Related Ligands: From High‐Spin Molecules and Single‐Molecule Magnets to Coordination Polymers, and from Structural Aesthetics to an Exciting New Reactivity Chemistry of Coordinated Ligands

Synthesis, properties and crystal structures of nitrobenzoatocopper(II) complexes with pyrazinecarboxamide

trans-Bis(dimethyl sulfoxide-κO)bis(3-oxo-3,4-dihydroquinoxaline-2-carboxylato-κ²N¹,O²)copper(II)

Contact Info

Product

Resources

About

Metal(II)-promoted hydrolysis of pyridine-2-carbonitrile to pyridine-2-carboxylic acid. The structure of [Cu(pyridine-2-carboxylate)2] · 2H2O

Cited by 46 publications

References 10 publications

Adventures in the Coordination Chemistry of Di‐2‐pyridyl Ketone and Related Ligands: From High‐Spin Molecules and Single‐Molecule Magnets to Coordination Polymers, and from Structural Aesthetics to an Exciting New Reactivity Chemistry of Coordinated Ligands

Adventures in the Coordination Chemistry of Di‐2‐pyridyl Ketone and Related Ligands: From High‐Spin Molecules and Single‐Molecule Magnets to Coordination Polymers, and from Structural Aesthetics to an Exciting New Reactivity Chemistry of Coordinated Ligands

Synthesis, properties and crystal structures of nitrobenzoatocopper(II) complexes with pyrazinecarboxamide

trans-Bis(dimethyl sulfoxide-κO)bis(3-oxo-3,4-dihydroquinoxaline-2-carboxylato-κ2N1,O2)copper(II)

Contact Info

Product

Resources

About

trans-Bis(dimethyl sulfoxide-κO)bis(3-oxo-3,4-dihydroquinoxaline-2-carboxylato-κ²N¹,O²)copper(II)