Untitled

The X-ray diffraction and conformational study of bis(4-chloroquinoline-N-oxide)hydrogen tribromide is performed. Two conformations corresponding to the minima on the energy curve are found by DFT using the ABINIT software. The model of one of the conformers generally matches with the structure determined experimentally for this compound using X-ray diffraction. In both instances, the structure with the dihedral angle (quinoline -N-O-H) close to 90° is most favorable, which is explained in terms of resonance theory and steric factors. It is concluded that oxygen atoms in the complex are in the sp 3 hybridization state and the sp 2 hybrid state of the oxygen atom is not possible here due to steric factors.

show abstract

“…A similar formation of hydrogen tribromide salts is not unusual and described in the literature [11,12].…”

Section: Resultssupporting

confidence: 70%

Conformational and structural analysis of bis(4-chloroquinoline-N-oxide)hydrogen tribromide

2015

View full text Add to dashboard Cite

show abstract

“…2‐Bromo‐1‐(thiophen‐2‐yl)ethanone (26): Column chromatography (silica gel, toluene/hexanes 1:1) afforded the product as a yellow solid (1333 mg, 65 %); R f =0.24 (toluene/hexanes 1:1); mp: 29–30 °C (lit 49. mp: 33–35 °C); 1 H NMR (400 MHz, CDCl 3 ): δ =4.36 (s, 2 H), 7.17 (dd, J =4.0 and 5.0 Hz, 1 H), 7.72 (dd, J =0.8 and 5.0 Hz, 1 H), 7.81 ppm (dd, J =0.8 and 4.0 Hz, 1 H); 13 C NMR (100 MHz, CDCl 3 ): δ =30.7, 128.5, 133.7, 135.3, 141.0, 184.5 ppm; HRMS‐EI m / z [ M ] + calcd for C 6 H 5 BrOS: 203.9244, found: 203.9244.…”

Section: Methodsmentioning

confidence: 99%

Evaluation of Flavonoid and Resveratrol Chemical Libraries Reveals Abyssinone II as a Promising Antibacterial Lead

et al. 2012

View full text Add to dashboard Cite

“…To our experience, tertiary amides react with halogens at very mild conditions with breaking some of their covalent bonds, and formation of new ones, − that can rise a problem for the initial adducts isolation and their structure elucidation. Among many structures tested, only N , N ′-diacylpiperazines produce relatively stable complexes with bromine (as well as with iodine and interhalogens) . Adducts of N , N ′-diacylpiperazines with halogens (interhalogens) have been obtained as shown in Scheme .…”

Section: Results and Discussionmentioning

confidence: 99%

Multiple Noncovalent Bonding in Halogen Complexes with Oxygen Organics. I. Tertiary Amides

Suponitsky

Burakov²,

Kanibolotsky

et al. 2016

J. Phys. Chem. A

View full text Add to dashboard Cite

The present work describes the structure and binding of adducts of N,N′-diacetylpiperazine with halogens and interhalogens based on combination of different experimental methods and quantum chemical calculations. On the basis of conductometric and spectro-photometric experimental results, behavior of complexes in the acetonitrile solution was described. The iodine adduct with N,N′-diacetylpiperazine fully degrades into components. Adducts of interhalogens I–X (X = Cl or Br) with N,N′-diacetylpiperazine in acetonitrile partially dissociate to anionic [X–I–X]− and cationic species. In the solid state, molecules are connected via CO···I, C–H···I, and Cl···Cl attractive interactions. N,N′-diacetylpiperazine···dihalogen complex is stabilized by simultaneous CO···I and C–H···I interactions. Such binding mode allows to explain the problems of the direct halogenation of acetyl-containing compounds with molecular halogens as reagents. We believe that the observed binding pattern can be used as prototypical for future design of halogeno complexes.

show abstract

Untitled

Cited by 11 publications

References 19 publications

Conformational and structural analysis of bis(4-chloroquinoline-N-oxide)hydrogen tribromide

Conformational and structural analysis of bis(4-chloroquinoline-N-oxide)hydrogen tribromide

Evaluation of Flavonoid and Resveratrol Chemical Libraries Reveals Abyssinone II as a Promising Antibacterial Lead

Multiple Noncovalent Bonding in Halogen Complexes with Oxygen Organics. I. Tertiary Amides

Contact Info

Product

Resources

About