The present stage of development of the chemistry of phosphorus-containing anthracene derivatives

Slitikov, P. V.; Petrov, A.; Rasadkina, E. N.; Нифантьев, Э. Е.

doi:10.1134/s1070363210010111

Cited by 5 publications

(4 citation statements)

References 45 publications

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“…Instead, pairs of pyridine rings face one another across an inversion centre (N1 ◊ ◊ ◊ H1a i C1 i = 2.83 A ˚) and are sandwiched between anthracene domains which associate through oblique CH anthracene ◊ ◊ ◊ p pyridine interactions (CH ◊ ◊ ◊ centroid = 2.82 A ˚). 11, 12 The change in orientation of the pyridine ring with respect to the anthracene unit observed within a molecule in the solid state on going from (E)-2 to (Z)-2 does not explain the dramatic shifts observed in solution for the pyridine 1 H NMR resonances (protons H A2 and H A3 ). These data are, however, consistent with the fact that, in solution, intramolecular interactions are dominant and lead to the pyridine ring lying over the anthracene domain.…”

Section: Synthesis and Characterization Of Isomers Ofmentioning

confidence: 98%

“…m.p. 160-162 • C. 1 H NMR (500 MHz, CDCl 3 ) d (ppm) 8.26 (s, 1H, H B10 ), 8.12 (d, J = 5.6 Hz, 2H, H A2 ), 8.08 (d, J = 12.1 Hz, 1H, H a/b ), 8.02 (d, J = 8.7 Hz, 2H, H B1/B4 ), 7.89 (d, J = 8.4 Hz, 2H, H B1/B4 ), 7.48 (m, 2H, H B2/B3 ), 7.43 (m, 2H, H B2/B3 ), 7.21 (d, J = 12.1 Hz, 1H, H a/b ) 7.02 (d, J = 5.6 Hz, 2H, H A3 ). 13 C NMR (126 MHz, CDCl 3 ) d (ppm) 193.4 (C C O ), 149.5 (C A2 ), 141.3 (C a/b ), 130.9 (C B4a/B9a ), 130.7 (C a/b ), 129.3 (C B4a/B9a ), 129.5 (C B9 ), 129.0 (C B1/B4 ),128.1 (C B10 ), 126.5 (C B2/B3 ), 125.3 (C B1/B4 ), 125.1 (C B2/B3 ), 120.5 (C A3 ), C A4 not observed.…”

Section: Compound (Z)-2mentioning

confidence: 99%

“…[Ag{(E)-2} 2 ][SbF 6 ] was isolated as red crystals (33.2 mg, 69.2%). 1 (Z)-2 (30.9 mg, 0.10 mmol) was dissolved in CH 2 Cl 2 (8 cm 3 ) and a solution of AgSbF 6 (17.1 mg, 0.050 mmol) in MeOH (4 cm 3 ) was added. The reaction mixture was stirred at room temperature for 10 min and then filtered.…”

Section: [Ag{(e)-2} 2 ][Sbf 6 ]mentioning

confidence: 99%

“…m.p. 168-170 • C. 1 H NMR (500 MHz, CDCl 3 ) d (ppm) 8.86 (overlapping d (J = 15.9 Hz) and d (AB) (J = 6.0 Hz), 3H, H a/b+A2 ), 8.50 (s, 1H, H B10 ), 8.27 (d, J = 8.5 Hz, 2H, H B1 ), 8.04 (d, J = 8.3 Hz, 2H, H B4 ), 7.82 (d (AB) , J = 6.1 Hz, 2H, H A3 ), 7.57-7.51 (overlapping, 4H, H B2+B3 ), 7.49 (d, J = 15.9 Hz, 1H, H a/b ). 13 C NMR (126 MHz, CDCl 3 ) d (ppm) 189.2 (C C O ), 151.2 (C A2 ), 144.1 (C a/b ), 131.5 (C B4a/B9a ), 130.1 (C a/b ), 129.9 (C B4a/B9a ), 129.5 (C B9 ), 129.3 (C B10 ), 129.25 (C B4 ), 127.0 (C B2/B3 ), 125.7 (C B2/B3 ), 125.2 (C B1 ), 121.8 (C A3 ), C A4 not observed.…”

Section: Introductionmentioning

confidence: 99%

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9-Anthracenyl-substitued pyridyl enones revisited: photoisomerism in ligands and silver(i) complexes

et al. 2011

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In solution, (E) to (Z)-isomerism is facile both in 3-(9-anthracenyl)-1-(pyridin-4-yl)propenone, 2, and in its silver(I) complex [Ag(2)(2)](+). The crystal structures of (E)-2, (Z)-2 and [Ag{(E)-2}(2)][SbF(6)] are presented, and the roles of edge-to-face and face-to-face π-interactions in the lattice are discussed. Solution NMR spectroscopic data suggest that the driving force for (E) to (Z) isomerization is intramolecular π-stacking of the pyridine and anthracene domains. The reversed enone 3-(9-anthracenyl)-1-(pyridin-4-yl)propen-3-one, (E)-3, and the silver(I) complex [Ag{(E)-3}(2)][SbF(6)] have been prepared and characterized, including a single crystal X-ray determination of the latter. Surprisingly, no π-stacking between anthracene or pyridine domains is observed in the solid state, and the crystal packing is dominated by Ag···F, CH(anthracene)···π-pyridine and CH···F interactions. In contrast to (E)-2 and [Ag{(E)-2}(2)](+), neither (E)-3 nor [Ag{(E)-3}(2)](+) undergoes photoisomerization in solution.

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Section: Synthesis and Characterization Of Isomers Ofmentioning

confidence: 98%

Section: Compound (Z)-2mentioning

confidence: 99%

Section: [Ag{(e)-2} 2 ][Sbf 6 ]mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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