Bindone

Crystal structure determination of rac-11'-(1-acetyl-1H-indazol-3-yl)-11',11a'-di-hydro-10'H,17'H-spiro-[indene-2,18 '-[5a,16b]methano-tri-indeno[1,2-b:1',2'-d:2'',1''-g]oxocine]-1,3,10',12',17'(10a 'H)-penta-one aceto-nitrile 1.5-solvate.[Pubmed:30319797]

Acta Crystallogr E Crystallogr Commun. 2018 Sep 18;74(Pt 10):1444-1447.

The title compound, C46H26N2O7.1.5CH3CN, is the aldol condensation product of Bindone with indazole-3-carbaldehyde followed by double inter-molecular cyclization. The asymmetric unit, which has monoclinic P21/c symmetry, contains two independent mol-ecules of the title compound and three aceto-nitrile mol-ecules. The title mol-ecule comprises a central eight-membered ring, which contains an enol-ester, from which five arms extend. The arms exhibit inter-molecular inter-actions within the crystal lattice between mol-ecules of the title compound and with co-crystallized solvent mol-ecules (aceto-nitrile).

Synthesis, Characterization and Photophysical Properties of Naphtho[2,3-b]Indolizine-6,11-Dione Derivatives.[Pubmed:26482522]

J Fluoresc. 2016 Jan;26(1):23-9.

This communication concerns the synthesis, structural characterization and fluorescent properties of novel naphtho[2,3-b]indolizine-6,11-dione derivatives. The target compound synthesized by one-pot multicomponent reaction between naphthoquinone, indandione and pyridine derivatives.The structures of synthesized compounds were characterized by IR, 1H NMR and 13C NMR analysis. The structure of two compounds was confirmed by single crystal X-ray diffraction. The photophysical properties of synthesized compounds were measured in a variety of organic solvents. The effects of substituents and solvents on UV-vis spectra and fluorescence emission were analyzed. All compounds were showed negative solvatochromism. The fluorescence emission of these derivatives was sensitive to solvent basicity and the large Stokes shifts (up to 129 nm, 4599 (cm-1)) were observed. The similar multicomponent reaction between naphthoquinone, Bindone and pyridine derivatives provide the formation of stable non-fluorescent compound possessing zwitter-ionic structure.

C(Ar)-H...O hydrogen bonds in substituted isobenzofuranone derivatives: geometric, topological, and NMR characterization.[Pubmed:22734703]

J Phys Chem A. 2012 Jul 26;116(29):7718-25.

Substituted isobenzofuranone derivatives 1a-3a and Bindone 4 are characterized by the presence of an intramolecular C(Ar)-H...O hydrogen bond in the crystal (X-ray), solution ((1)H NMR and specific and nonspecific IEF-PCM solvation model combined with MP2 and B3LYP methods), and gas (MP2 and B3LYP) phases. According to geometric and AIM criteria, the C(Ar)-H...O interaction weakens in 1a-3a (independent of substituent nature) and in 4 with the change in media in the following order: gas phase > CHCl(3) solution > DMSO solution > crystal. The maximum value of hydrogen bond energy is 4.6 kcal/mol for 1a-3a and 5.6 kcal/mol for 4. Both in crystals and in solutions, hydrogen bond strength increases in the order 1a < 2a < 3a with the rising electronegativity of the ring substituents (H < OMe < Cl). The best method for calculating (1)H NMR chemical shifts (delta(calcd) - delta(expl) < 0.7 ppm) of hydrogen bonded and nonbonded protons in 1a-3a and 1b-3b (isomers without hydrogen bonds) is the GIAO method at the B3LYP level with the 6-31G** and 6-311G** basis sets. For the C-H moiety involved in the hydrogen bond, the increase of the spin-spin coupling constant (1)J((13)C-(1)H) by about 7.5 Hz is in good agreement with calculations for C-H bond shortening and for blue shifts of C-H stretching vibrations (by 55-75 cm(-1)).

Aromatic C-H...O interactions in a series of bindone analogues. NMR and quantum mechanical study.[Pubmed:15624909]

J Org Chem. 2005 Jan 7;70(1):92-100.

The aromatic C-H...O hydrogen bonding within the series of the structurally relative indenone derivatives has been studied. The presence of the hydrogen bonds is corroborated by the large low-field chemical shifts of the protons involved in the hydrogen bond observed experimentally and reproduced by quantum mechanical calculations. Further confirmation is provided by analysis of the orbital overlap coefficients, (13)C NMR chemical shifts, and one-bond spin-spin coupling constants J((13)C-(1)H). The relationship between molecular geometry and (1)H NMR chemical shifts of involved protons has a complex nature, but the C-H...O distance is the principal factor.