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An experimental and theoretical NMR study of NH-benzimidazoles in solution and in the solid state: proton transfer and tautomerism
| Content Provider | Directory of Open Access Journals (DOAJ) |
|---|---|
| Author | M. Ángeles García José Elguero Carla I. Nieto Rosa M. Claramunt Ibon Alkorta Pilar Cabildo |
| Abstract | This paper reports the 1H, 13C and 15N NMR experimental study of five benzimidazoles in solution and in the solid state (13C and 15N CPMAS NMR) as well as the theoretically calculated (GIAO/DFT) chemical shifts. We have assigned unambiguously the "tautomeric positions" (C3a/C7a, C4/C7 and C5/C6) of NH-benzimidazoles that, in some solvents and in the solid state, appear different (blocked tautomerism). In the case of 1H-benzimidazole itself we have measured the prototropic rate in HMPA-d18. |
| Related Links | https://doi.org/10.3762/bjoc.10.168 |
| e-ISSN | 18605397 |
| DOI | 10.3762/bjoc.10.168 |
| Journal | Beilstein Journal of Organic Chemistry |
| Issue Number | 1 |
| Volume Number | 10 |
| Language | English |
| Publisher | Beilstein-Institut |
| Publisher Date | 2014-01-01 |
| Publisher Place | Germany |
| Access Restriction | Open |
| Subject Keyword | Science Organic Chemistry Cpmas Dnmr Giao Proton Transfer Tautomerism |
| Content Type | Text |
| Resource Type | Article |