Folded conformations due to arene interactions in dissymmetrical and symmetrical butylidene linker models based on pyrazolo[3,4-d]pyrimidine, purine and 7-deazapurine
IR@CDRI: CSIR-Central Drug Research Institute, Lucknow
View Archive Info| Field | Value | |
| Creator |
Avasthi, Kamlakar
Shukla, Lakshmi Kant, Ruchir Ravikumar, Krishnan |
|
| Date |
2014-08-14T07:27:50Z
2014-08-14T07:27:50Z 2014 |
|
| Identifier |
Acta Crystallographica Section C Structural Chemistry 2014, 70(6), 555-61
http://hdl.handle.net/123456789/1369 |
|
| Description |
Abstract Butylidene linker models 1-(2-(2,6-dimethylsulfanyl-9H-purin-9-yl)-2-methylenepropane-4,6-dimethylsulfanyl)-1H-pyrazolo[3,4-d]pyrimidine, (XI), C18H20N8S4, 7,7′-(2-methylenepropane-1,3-diyl)bis(3-methyl-2-methylsulfanyl-3H-pyrrolo[2,3-d]pyrimidin-4(7H)-one), (XIV), C20H22N6O2S2 and 7-(2-(4,6-dimethylsulfanyl-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-2-methylenepropane-3-methyl-2-methylsulfanyl-3H-pyrrolo[2,3-d]pyrimidin-4(7H)-one, (XV), C19H21N7OS3 show folded conformations in solution as shown by proton NMR analysis. This folding carries over to solid state for all models as revealed by X-ray crystallography due to intramolecular π‒π interactions. Whereas, only one model (XIV) shows additional intramolecular C‒H…π interactions in solid state. To the best of our knowledge, this is the first report using pyrrolo[2,3-d]pyrimidine nucleus for such kind of study. In addition to the π‒π interactions, crystal structures are also stabilized by other weak intermolecular C‒H…S/N/O and/or S…N/S interactions.
|
|
| Format |
792708 bytes
application/pdf |
|
| Language |
en
|
|
| Relation |
CSIR-CDRI communication No. 8673
|
|
| Subject |
Arene Interactions
Butylidene Linker Propylene Linker Purine 7-Deazapurine Pyrazolo[3,4-D]Pyrimidine |
|
| Title |
Folded conformations due to arene interactions in dissymmetrical and symmetrical butylidene linker models based on pyrazolo[3,4-d]pyrimidine, purine and 7-deazapurine
|
|
| Type |
Article
|
|