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

Journal Article · Fri Dec 15 04:00:00 EST 2017 · Crystallography Reports

DOI:https://doi.org/10.1134/S1063774517070343· OSTI ID:22758294

Xiaofeng, J. S.; Yi, H. P.; Mo, Z. L.

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, Journal Name: Crystallography Reports Journal Issue: 7 Vol. 62; ISSN 1063-7745; ISSN CYSTE3
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
ANIONS
CATIONS
CRYSTAL STRUCTURE
FORMALDEHYDE
HYDROGEN
METHANE
MOLECULES
MONOCRYSTALS
PHENANTHROLINES
SALTS
SYNTHESIS
X-RAY DIFFRACTION