Two new copper and nickel complexes of pyridine-2,6-dicarboxylic acid N-oxide and their proton transferred salts: Solid state and DFT insights

Mirzaei, Masoud; Eshtiagh‐Hosseini, Hossein; Bazargan, Maryam; Mehrzad, Farzaneh; Shahbazi, Mina; Mague, Joel T.; Bauzá, Antonio

doi:10.1016/j.ica.2015.08.030

Cited by 18 publications

(7 citation statements)

References 54 publications

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“…The absorptions at 3000−3500 cm −1 can be assigned to the NH and OH stretching vibrations of the amino groups or O−H in the carboxylate group of the H 2 pydco ligand and water molecules, respectively. 32,33 The strong band ν as (COO − ) and ν s (COO − ) stretching modes appeared for free H 2 pydco at 1726 and 1419 cm −1 , respectively, which were shifted in all of the compounds to lower wavenumbers in the ranges 1695−1626 and 1407−1365 cm −1 , respectively. Furthermore, in the infrared spectrum of H 2 pydco (Figure S1) a strong band at 1230 cm −1 can be attributed to the presence of an N−O group.…”

Section: ■ Methodsmentioning

confidence: 96%

Recurrent Supramolecular Motifs in a Series of Acid–Base Adducts Based on Pyridine-2,5-Dicarboxylic Acid N-Oxide and Organic Bases: Inter- and Intramolecular Hydrogen Bonding

Mirzaei

Sadeghi

Molčanov

et al. 2020

Crystal Growth & Design

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Salts and ionic cocrystals simultaneously comprising N-oxide and carboxylic acid functional groups constitute a very fertile ground for the investigation of various proton transfer phenomena. This is because such compounds combine two types of proton transfer: that is, inter-and intramolecular hydrogen bonding in acid−base systems. To this end, a series of novel salts based on pyridine-2,5-dicarboxylic acid N-oxide (H 2 pydco) as an organic acid and 2,4,6-triamino-1,3,5-triazine (tata), 2-aminopyrimidine (2a-pym), 2-amino-6-methylpyridine (2a-6mpy), 1,10phenanthroline (phen), and 9-aminoacridine (9a-acr) as organic bases have been synthesized and characterized by elemental analyses, infrared spectroscopy, and single-crystal X-ray diffraction: (Htata) + (Hpydco) − (1), (H2a-pym) + (Hpydco) − (2), (H2a-6mpy) + (Hpydco) − (3A,B), [(Hphen) + (Hpydco) − ](H 2 pydco) (4), and [(H9a-acr) + (Hpydco) − ]•EtOH (5). The unit cells of 3A and 3B differ slightly; however, 3A crystallizes in a chiral orthorhombic space group P2 1 2 1 2 1 , while 3B crystallizes in the achiral space group P2 1 /n. In both cases, the asymmetric unit comprises one cation and one anion. The influence of different organic cations on the packing of Hpydco − in the crystal lattice is studied. The most important feature of these crystals is the presence of extensive O− Hbond networks, which form base-dependent supramolecular synthons: 1, 2, and 3A,B comprise an α-aminopyridinium moiety, and all involve the hydrogen-bonded motif R 2 2 (8) with the Hpydco − anion. Compounds 4 and 5, which lack the α-aminopyridinium moiety, reveal different hydrogen-bonding patterns. The interaction energies of each individual hydrogen bond have been estimated using the quantum theory of "atoms-in-molecules", which led us to the identification of the energetically favorable antielectrostatic N−H•••N hydrogen bonds (stabilization energy of 4.0 kcal/mol) between positively charged melaminium species in 1. It has been also established that charge-assisted hydrogen bonding does not always offer an energetic advantage over "noncharged" hydrogen bonds. With the use of Hirshfeld surface (HS) analysis we have also explored the influence of the protonation state of pydco species on the composition of contact contributions, as well as established specific properties of their 2D fingerprint plots. Finally, a comment is provided on the applicability of HS analysis for the exploration of polymorphs featuring intramolecular proton transfer.

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Section: ■ Methodsmentioning

confidence: 96%

Recurrent Supramolecular Motifs in a Series of Acid–Base Adducts Based on Pyridine-2,5-Dicarboxylic Acid N-Oxide and Organic Bases: Inter- and Intramolecular Hydrogen Bonding

Mirzaei

Sadeghi

Molčanov

et al. 2020

Crystal Growth & Design

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“…The bond lengths and angles characterizing the geometry of the acridine moieties in the cation are characteristic of acridinium salts. [42][43][44][45][46][47][48] The two acridine ring systems are almost planar (the average deviation from planarity is 0.0311(3) Å) and parallel (0.0(0)1). The carboxyl groups are twisted at an angle of 84.8(1)1 with respect to the relevant acridine skeletons.…”

Section: Resultsmentioning

confidence: 99%

Structure, formation, thermodynamics and interactions in 9-carboxy-10-methylacridinium-based molecular systems

et al. 2016

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“…In continuation of our previous work with based-oxide-N carboxylate compounds, [18][19][20][21][22][23] we have chosen pyrazine (pz) and 1,10-phenanthroline (phen) as based-donor-N ligands to survey the effect of the bridging and chelating behavior in terms of structural expansion. H 2 pydco is also found to show diverse coordination modes (chelate and bridge) so it was further anticipated that it might show interesting structural properties due to its O-donor nature.…”

Section: Introductionmentioning

confidence: 99%

On the importance of π-stacking interactions in the complexes of copper and zinc bearing pyridine-2,6-dicarboxylic acid N-oxide and N-donor auxiliary ligands

et al. 2022

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Two new copper and nickel complexes of pyridine-2,6-dicarboxylic acid N-oxide and their proton transferred salts: Solid state and DFT insights

Cited by 18 publications

References 54 publications

Recurrent Supramolecular Motifs in a Series of Acid–Base Adducts Based on Pyridine-2,5-Dicarboxylic Acid N-Oxide and Organic Bases: Inter- and Intramolecular Hydrogen Bonding

Recurrent Supramolecular Motifs in a Series of Acid–Base Adducts Based on Pyridine-2,5-Dicarboxylic Acid N-Oxide and Organic Bases: Inter- and Intramolecular Hydrogen Bonding

Structure, formation, thermodynamics and interactions in 9-carboxy-10-methylacridinium-based molecular systems

On the importance of π-stacking interactions in the complexes of copper and zinc bearing pyridine-2,6-dicarboxylic acid N-oxide and N-donor auxiliary ligands

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