Proficiency of the electron-deficient 1,3,5-triazine ring to generate anion–π and lone pair–π interactions

Costa, José Sánchez; Castro, Adriana Gonzalez; Pievo, Roberta; Roubeau, Olivier; Modec, Barbara; Kozlevčar, Bojan; Teat, Simon J.; Gámez, Patrick; Reedijk, Jan

doi:10.1039/c004478d

Cited by 35 publications

(18 citation statements)

References 38 publications

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“…Later, the same group reported the crystal structure of a co-ordination complex, [Cu(Hspet)(NO 3 ) 2 ](NO 3 )Á0.5H 2 O, synthesized from the reaction of the ligand 2,4,6-tris-N-[N-2-(methylsulfanyl)-N-(pyridine-2-ylmethyl)ethanamine]-1,3,5-triazine (spet) with copper II nitrate. 81 This crystal structure is depicted in Fig. 14, and it shows that the third substituent nitrogen atom (N19) of the 1,3,5-triazine ring is in close contact with the triazine ring of the adjacent co-ordination molecule, and the N19 atom of the latter co-ordination molecule is also in close contact with the centroid of the triazine ring of the former co-ordination molecule.…”

Section: Significance Of the Np* Interaction In Materialsmentioning

confidence: 99%

“…The np* interaction plays a significant role in the structures of not only biomacromolecules but also materials. [78][79][80][81][82][83][84][85] There are quite extensive reports in the literature which show the existence of the np* interaction as well as its role in the supramolecular self assembly of molecules to give rise to specific structures of materials. Reedijk and co-workers have named this interaction as a new supramolecular bond.…”

Section: Significance Of the Np* Interaction In Materialsmentioning

confidence: 99%

“…Thus, a double lpÁ Á Áp interaction holds the two complexes together in their crystal packing. 81 Mukhopadhyay hydrogen bonding. The oxygen atom (O3) of the non-coordinating carbonyl group of malonate is in close contact (3.2 Å) with the center of the 2-aminopyridine ring.…”

Section: Significance Of the Np* Interaction In Materialsmentioning

confidence: 99%

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The n → π* interaction: a rapidly emerging non-covalent interaction

Singh

Das

2015

Phys. Chem. Chem. Phys.

267

216

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This perspective describes the current status of a recently discovered non-covalent interaction named as the n → π* interaction, which is very weak and counterintuitive in nature. In this review, we have provided a brief overview of the widespread presence of this interaction in biomacromolecules, small biomolecules and materials, as well as the physical nature of this interaction explored using various experimental and theoretical techniques. It has been found that this interaction is equally important to other non-covalent interactions for the stability and specific structures of biomolecules and materials. An in-depth understanding of this interaction can help in designing more efficient functional materials as well as drugs. The review also provides a future outlook in terms of exploring the detailed functional role of this interaction in biological processes and its direct spectroscopic evidence, which other commonly known non-covalent interactions (conventional hydrogen bonding, π-hydrogen bonding, π-stacking, etc.) have.

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Section: Significance Of the Np* Interaction In Materialsmentioning

confidence: 99%

Section: Significance Of the Np* Interaction In Materialsmentioning

confidence: 99%

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The n → π* interaction: a rapidly emerging non-covalent interaction

Singh

Das

2015

Phys. Chem. Chem. Phys.

267

216

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“…35c triazine ring. It should also be noted that the relatively small distance between the bromido ligand can be enforced by geometrical restrictions [124].…”

Section: Azoimidazole Ligandsmentioning

confidence: 99%

Guanidine Metal Complexes for Bioinorganic Chemistry and Polymerisation Catalysis

Stanek

Rösener

Metz

et al. 2015

Topics in Heterocyclic Chemistry

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Guanidines are highly useful ligands which have conquered coordination chemistry within the last 20 years. Their CN 3 moiety allows multiple substitution patterns which enables tailoring them to a large variety of applications, ranging from bioinorganic coordination chemistry via medicinal chemistry to polymerisation catalysis. In bioinorganic chemistry, guanidines gave important stimuli in the modelling of copper type 1, 2 and 3 enzymes. This review provides with a comprehensive overview on complexes which have been reported with neutral guanidine ligands. Peralkylated guanidines as well as bicyclic or more complex guanidine-comprising entities are described in their coordination chemistry with transition and main-group metals. The structural features of the complexes as well as their most prominent features in bioinorganic chemistry or polymerisation catalysis are highlighted. Hereby, the role of the delocalisation of the positive charge within the guanidine unit gained during coordination is discussed in its importance for efficient and robust coordination. The delocalisation within the CN 3 unit can be measured by the structural value ρ which is discussed for numerous systems. The charge delocalisation makes neutral guanidines versatile and efficient for the stabilisation of highly different coordination modes and a large variety of oxidation states.

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“…The ligand 2-(methylsulfanyl)-N-(pyridin-2-ylmethylidene)aniline (L) was synthesized following a literature procedure [20]. A solution of 2-(methylthio)aniline (0.64 g, 4.6 mmol) and fresh distilled pyridine-2-carboxaldehyde (0.50 g, 4.6 mmol) in toluene (50 mL) was refluxed for 24 h. The reaction mixture was then filtered and the solvent was evaporated under reduced pressure.…”

Section: Ligand Synthesismentioning

confidence: 99%

Zinc and cadmium halide compounds with the tridentate ligand 2-(methylsulfanyl)-N-(pyridin-2-ylmethylidene)aniline showing yellow luminescence

González-Castro

Mutikainen

et al. 2016

Polyhedron

Self Cite

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Five mononuclear complexes, i.e. ZnLCl 2 (1), [ZnLBr 2 ](CH 3 CN) (2), ZnLBr 2 (3), CdLCl 2 (4), and CdLBr 2 (5), with L= 2-(methylsulfanyl)-N-(pyridin-2-ylmethylidene)aniline, have been synthesized and characterized. For [ZnLBr 2 ](CH 3 CN) only a few crystals were obtained from the main batch of ZnLBr 2 .Their crystal structures and solid-state luminescence properties both at room temperature and 77 K have been investigated. All compounds contain 5-coordinated Zn (II) or Cd(II) ions in a square-pyramidal geometry, distorted towards trigonal bipyramidal. The phase purity of all compounds has been evaluated by Powder XRD and IR. All five compounds show photoluminescent properties both at room temperature and 77 K. In the solid state, the compounds exhibit yellow luminescence with the maximum of emission at around 540 nm. By cooling down to 77 K, the shape and position of the emission spectra of all these compounds remains more or less constant.

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Proficiency of the electron-deficient 1,3,5-triazine ring to generate anion–π and lone pair–π interactions

Cited by 35 publications

References 38 publications

The n → π* interaction: a rapidly emerging non-covalent interaction

The n → π* interaction: a rapidly emerging non-covalent interaction

Guanidine Metal Complexes for Bioinorganic Chemistry and Polymerisation Catalysis

Zinc and cadmium halide compounds with the tridentate ligand 2-(methylsulfanyl)-N-(pyridin-2-ylmethylidene)aniline showing yellow luminescence

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