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- Title
Folded conformations due to arene interactions in dissymmetric and symmetric butylidene-linker models based on pyrazolo[3,4- d]pyrimidine, purine and 7-deazapurine.
- Authors
Avasthi, Kamlakar; Shukla, Lakshmi; Kant, Ruchir; Ravikumar, Krishnan
- Abstract
The butylidene-linker models 1-[2-(2,6-dimethylsulfanyl-9 H-purin-9-yl)-2-methylidenepropyl]-4,6-bis(methylsulfanyl)-1 H-pyrazolo[3,4- d]pyrimidine, C18H20N8S4, (XI), 7,7′-(2-methylidenepropane-1,3-diyl)bis[3-methyl-2-methylsulfanyl-3 H-pyrrolo[2,3- d]pyrimidin-4(7 H)-one], C20H22N6O2S2, (XIV), and 7-[2-(4,6-dimethylsulfanyl-1 H-pyrazolo[3,4- d]pyrimidin-1-yl)-2-methylidenepropyl]-3-methyl-2-methylsulfanyl-3 H-pyrrolo[2,3- d]pyrimidin-4(7 H)-one, C19H21N7OS3, (XV), show folded conformations in solution, as shown by 1H NMR analysis. This folding carries over to the crystalline state. Intramolecular π-π interactions are observed in all three compounds, but only (XIV) shows additional intramolecular C-H...π interactions in the solid state. As far as can be established, this is the first report incorporating the pyrrolo[2,3- d]pyrimidine nucleus for such a study. In addition to the π-π interactions, the crystal structures are also stabilized by other weak intermolecular C-H...S/N/O and/or S...N/S interactions.
- Subjects
CRYSTAL structure; CRYSTALLOGRAPHY; AROMATIC compounds; PURINES; HETEROCYCLIC compounds; PYRIMIDINES
- Publication
Acta Crystallographica Section C: Structural Chemistry, 2014, Vol 70, Issue 6, p555
- ISSN
2053-2296
- Publication type
Article
- DOI
10.1107/S2053229614009449