Cobalt(II)-mediated synthesis of 2,6-bis[5,7-di-tert-butyl-1,3-benzoxazol-2-yl]-pyridine: Structural analysis and coordination behavior

Garza-Ortiz, Ariadna; Martínez, P.; Duarte-Hernández, Angélica M.; Mijangos, Edgar; Flores‐Álamo, Marcos; Pérez-Casas, Carol; Camacho‐Camacho, Carlos; Contreras, Rosalinda; Flores‐Parra, Angelina; Reedijk, Jan; Barba-Behrens, Noráh

doi:10.1016/j.molstruc.2012.09.078

Cited by 5 publications

(4 citation statements)

References 39 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The conformer (VI) with two close nitrogen atoms with lone pairs in the inner side of the molecule has more energy (26.0 kJ · mol –1 ), probably due to repulsion between the lone pairs. Stabilization of conformers (III–V) could be due to the oxygen atom ability to receive lone pair interactions 22–25. Tautomer (V) is slightly less stable than conformer (III), due to the less density at the nitrogen lone pair of the chlorobenzoxazole group, which could stabilize less its proximity with the neighboring oxygen atom.…”

Section: Resultsmentioning

confidence: 99%

“…It is quite interesting that the oxygen atom does not have a strong repulsion effect when it is close to another oxygen or nitrogen atom. The explanation is due to the N→O or O→O interactions 22–25…”

Section: Resultsmentioning

confidence: 99%

“…The explanation is due to the NǞO or OǞO interactions. [22][23][24][25] The destabilization factors are the presence of two nitrogen lone pair in the 1,3-position of the outer side, their repulsion increases the energy. Protonation at the nitrogen atom of the chlorobenzoxazole is less favored due to minor electronic density in this group.…”

Section: Resultsmentioning

confidence: 99%

“…Stabilization of conformers (III-V) could be due to the oxygen atom ability to receive lone pair interactions. [22][23][24][25] Tautomer (V) is slightly less stable than conformer (III), due to the less density at the nitrogen lone pair of the chlorobenzoxazole group, which could stabilize less its proximity with the neighboring oxygen atom. Tautomers (VII-VIII), having the proton at the endocyclic nitrogen atom in the external side of the molecule, are less stable because they do not present a hydrogen bond, and again the difference between them is due to the position of the proton in the different heterocycles.…”

Section: Resultsmentioning

confidence: 99%

See 3 more Smart Citations

Structural Analysis and Coordination Compounds of [(1,3‐Benzoxazol‐2‐yl)‐(5‐chloro‐1,3‐benzoxazol‐2‐yl)]amine

Téllez¹,

Ramírez-Trejo²,

Vieto-Peña³

et al. 2013

Zeitschrift anorg allge chemie

Self Cite

View full text Add to dashboard Cite

A novel [(1,3-benzoxazol-2-yl)-(5-chloro-1,3-benzoxazol-2yl)]amine (L) (1) compound was synthesized. The molecule has a nitrogen atom between 1,3-benzoxazol-2-yl and 5-chloro-1,3-benzoxazol-2-yl groups. For compound 1 there are twelve possible conformers and tautomers. Ab initio calculations were performed in order to investigate the more stable structures. Three crystals of compound Materials and Methods: All chemicals were reagent grade: methanol (J. T. Baker), 2-amino-5-chloro-benzoxazole (Aldrich); NaOH, CS 2 , CH 3 I, DMF, THF, Co(CH 3 CO 2 ) 2 ·4H 2 O, and Ni(CH 3 CO 2 ) 2 ·4H 2 O. They were used without further purification. Melting points were determined with an Electrothermal 9100 apparatus. FAB mass spectra were obtained with a Jeol model SX-102 spectrometer. Elemental analyses were carried out with a Fisions Instruments EA-1108. An FT IR spectrometer (Perkin-Elmer Model 1605) was used for obtaining IR spectra of solid samples in KBr pellets (4000-400 cm -1 ). The UV/ Vis/NIR spectra (diffuse reflectance) were recorded with a Varian Cary 5E spectrophotometer. NMR spectra were recorded with a VARIAN model Unity Inova (300 and 400 MHz) or a Bruker-Avance-DPX 300 by using [D 6 ]DMSO or CDCl 3 as solvent. Magnetic susceptibility measurements were performed on pulverized samples at room temperature with a Johnson Matthey DG8 5HJ balance. X-ray single crystal data for 1a, 1b, and1c were collected with a KAPPA-CCD area detector diffractometer. The crystal structures were determined and refined with the SHELXS97 and Crystals programs. [18,19] Ab initio cal-[(1,3-Benzoxazol-2-yl)-(5-chloro-1,3-benzoxazol-2-yl)]amine culations were performed in order to obtain the minimum energy structure for the twelve tautomers and conformers of compound 1 using the Gaussian 98 package. [20] Geometries were checked to be the minimal by means of the frequency analysis.

show abstract

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

See 2 more Smart Citations

Structural Analysis and Coordination Compounds of [(1,3‐Benzoxazol‐2‐yl)‐(5‐chloro‐1,3‐benzoxazol‐2‐yl)]amine

Téllez¹,

Ramírez-Trejo²,

Vieto-Peña³

et al. 2013

Zeitschrift anorg allge chemie

Self Cite

View full text Add to dashboard Cite

show abstract

Copper(II)–diaminosarcophagine‐functionalized SBA‐15: a heterogeneous nanocatalyst for the synthesis of benzimidazole, benzoxazole and benzothiazole derivatives under solvent‐free conditions

Bardajee

Mohammadi

Kakavand

2015

Applied Organom Chemis

View full text Add to dashboard Cite

Solvent‐free organic reactions were studied over periodic mesoporous silica (SBA‐15) containing a Cu(II) organometallic complex. This heterogeneous catalyst was achieved by coordination of Cu(II) ions with the diaminosarcophagine ligand and then its grafting onto the surface of SBA‐15. This catalyst displayed ordered mesoporous channels, which implies an extremely high dispersion of the Cu(II) complex and the convenient diffusion of reactant molecules into the pore channels. Therefore, this catalyst can offer high activity and also facile separation or recycling when compared with its homogeneous counterparts. Copyright © 2015 John Wiley & Sons, Ltd.

show abstract

Synthesis, structural characterization and dielectric properties of (C6H9N2)2(Hg0.75Cd0.25)Cl4 compound

Elwej¹,

Hamdi²,

Hannachi³

et al. 2014

Spectrochimica Acta Part A: Molecular and Biomolecular Spectros

View full text Add to dashboard Cite

Cobalt(II)-mediated synthesis of 2,6-bis[5,7-di-tert-butyl-1,3-benzoxazol-2-yl]-pyridine: Structural analysis and coordination behavior

Cited by 5 publications

References 39 publications

Structural Analysis and Coordination Compounds of [(1,3‐Benzoxazol‐2‐yl)‐(5‐chloro‐1,3‐benzoxazol‐2‐yl)]amine

Structural Analysis and Coordination Compounds of [(1,3‐Benzoxazol‐2‐yl)‐(5‐chloro‐1,3‐benzoxazol‐2‐yl)]amine

Copper(II)–diaminosarcophagine‐functionalized SBA‐15: a heterogeneous nanocatalyst for the synthesis of benzimidazole, benzoxazole and benzothiazole derivatives under solvent‐free conditions

Synthesis, structural characterization and dielectric properties of (C6H9N2)2(Hg0.75Cd0.25)Cl4 compound

Contact Info

Product

Resources

About