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The subtle balance of weak supramolecular interactions: The hierarchy of halogen and hydrogen bonds in haloanilinium and halopyridinium salts
| Content Provider | Semantic Scholar |
|---|---|
| Author | Raatikainen, Kari Cametti, Massimo Rissanen, Kari |
| Copyright Year | 2010 |
| Abstract | THE SERIES OF HALOANILINIUM AND HALOPYRIDINIUM SALTS: 4-IPhNH₃Cl (1), 4-IPhNH₃Br (5), 4-IPhNH₃H₂PO₄ (6), 4-ClPhNH₃H₂PO₄ (8), 3-IPyBnCl (9), 3-IPyHCl (10) and 3-IPyH-5NIPA (3-iodopyridinium 5-nitroisophthalate, 13), where hydrogen or/and halogen bonding represents the most relevant non-covalent interactions, has been prepared and characterized by single crystal X-ray diffraction. This series was further complemented by extracting some relevant crystal structures: 4-BrPhNH₃Cl (2, CCDC ref. code TAWRAL), 4-ClPhNH₃Cl (3, CURGOL), 4-FPhNH₃Cl (4, ANLCLA), 4-BrPhNH₃H₂PO₄, (7, UGISEI), 3-BrPyHCl, (11, CIHBAX) and 3-ClPyHCl, (12, VOQMUJ) from Cambridge Structural Database for sake of comparison. Based on the X-ray data it was possible to highlight the balance between non-covalent forces acting in these systems, where the relative strength of the halogen bonding C-X...A⁻ (X = I, Br or Cl) and the ratio between the halogen and hydrogen bonds [C-X...A⁻ : D-H...A⁻] varied across the series. |
| File Format | PDF HTM / HTML |
| DOI | 10.3762/bjoc.6.4 |
| PubMed reference number | 20502514 |
| Journal | Medline |
| Volume Number | 6 |
| Alternate Webpage(s) | http://www.beilstein-journals.org/bjoc/content/supplementary/1860-5397-6-4-S1.pdf |
| Alternate Webpage(s) | http://www.beilstein-journals.org/bjoc/content/pdf/1860-5397-6-4.pdf |
| Alternate Webpage(s) | https://doi.org/10.3762/bjoc.6.4 |
| Journal | Beilstein journal of organic chemistry |
| Language | English |
| Access Restriction | Open |
| Content Type | Text |
| Resource Type | Article |
