Intramolecular Six-Membered and Three-Center C-H center dot center dot center dot O Hydrogen Bonding in 1,4-Diphenyl-1,2,3-Triazoles
Zhu, YY; Wang, GuiTao; Wang, RenX; Li, ZT
| HERO ID | 4854529 |
|---|---|
| In Press | No |
| Year | 2009 |
| Title | Intramolecular Six-Membered and Three-Center C-H center dot center dot center dot O Hydrogen Bonding in 1,4-Diphenyl-1,2,3-Triazoles |
| Authors | Zhu, YY; Wang, GuiTao; Wang, RenX; Li, ZT |
| Journal | Crystal Growth & Design |
| Volume | 9 |
| Issue | 11 |
| Page Numbers | 4778-4783 |
| Abstract | This paper reports the first example of the intramolecular three-center C-H center dot center dot center dot O hydrogen bonding. Nine 1,4-di(2-methoxy and/or i-butoxy)phenyl-1,2,3-triazole derivatives, that is, 1-9, are prepared. The X-ray diffraction studies reveal that 1, 2, and 4, which bear a methoxyl or i-butoxyl group on the N-1- or C-4-substituted benzene ring, form a six-membered C-H center dot center dot center dot O hydrogen bond between the C(5)-H of their triazole unit and the alkoxyl O, while 5-8, which bear two methoxyl and/or i-butoxyl groups on the similar benzene rings, form two three-center C-H center dot center dot center dot O hydrogen bonds. It is also found that in most cases the hydrogen bond oil the C-4 side is shorter than that oil the N-1 side and both of them can be stabilized by the aromatic stacking and other intermolecular interactions. The (NOESY) (1)H NMR experiments in CDCl(3) and CDCl(3)-DMSO-d(6) mixture (4: 1) support that both the six-membered and the three-center C-H center dot center dot center dot O hydrogen bonds also exist in solution. |
| Doi | 10.1021/cg9006197 |
| Wosid | WOS:000271272900030 |
| Is Certified Translation | No |
| Dupe Override | No |
| Is Public | Yes |