Condensation Reaction of 1,2,3,4-Tetrahydro-1,10-phenanthroline and Formaldehyde: Synthesis and Crystal Structures of Bis(1,2,3,4-tetrahydro-1,10-phenanthroline-6-yl)methane and Its p-Toluenesulfonate Salt
A new heterocyclic compound, bis(1,2,3,4-tetrahydro-1,10-phenanthroline-6-yl) methane (1), was obtained by the condensation reaction of 1,2,3,4-tetrahydro-1,10-phenanthroline (tphen) and formaldehyde (HCHO). The p-toluenesulfonate salt of 1, (ptsa){sub 2} · (1H{sub 2}) (2, ptsaH = p-toluenesulfonic acid), is also synthesized and characterized. Cystal structures of 1 and 2 are determined by X-ray single crystal diffraction. The molecules of 1 form a 1D helix supramolecular chain by weak N−H···N hydrogen bonds, while in crystal 2, the 1H{sub 2}{sup 2+} cations and ptsa{sup -} anions are alternately connected by strong N−H···O hydrogen bonds and generate a 1D zigzag supramolecular chain. The result also proves that the condensation reaction of tphen can provide its C6 condensation product with high regioselectivity.
- OSTI ID:
- 22758294
- Journal Information:
- Crystallography Reports, Vol. 62, Issue 7; Other Information: Copyright (c) 2017 Pleiades Publishing, Inc.; Country of input: International Atomic Energy Agency (IAEA); ISSN 1063-7745
- Country of Publication:
- United States
- Language:
- English
Similar Records
Solvent induced synthesis, structure and properties of coordination polymers based on 5-hydroxyisophthalic acid as linker and 1,10-phenanthroline as auxiliary ligand
Synthesis and properties of a new chelating ligand, 4,7-bis(dicyanomethylidene)-1,4,7,10-tetrahydro-1,10-phenanthroline