Cation-Induced π-Stacking

• Published in: Journal of organic chemistry Vol. 73; no. 10; pp. 3931 - 3934
• Main Authors: Bosch, Eric, Barnes, Charles L, Brennan, Nathan L, Eakins, Galen L, Breyfogle, Bryan E
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 16.05.2008; Amer Chemical Soc
• Subjects: 2,2'-Dipyridyl - chemical synthesis; 2,2'-Dipyridyl - chemistry; Cations - chemical synthesis; Cations - chemistry; Chemistry; Chemistry, Organic; Coordination compounds; Copper - chemistry; Crystallography, X-Ray; Electrochemistry; Exact sciences and technology; Inorganic chemistry and origins of life; Ligands; Mesylates - chemistry; Models, Molecular; Molecular Structure; Organometallic Compounds - chemical synthesis; Organometallic Compounds - chemistry; Palladium - chemistry; Phenanthrenes - chemistry; Physical Sciences; Preparations and properties; Science & Technology; Silver - chemistry; CRYSTAL-STRUCTURES; COMPLEX; Complexation; Phenanthrene derivatives; Nitrogen heterocycle; Ligand; Palladium II; Bipyridines; NMR spectrometry; X ray diffraction; Pyridine derivatives; Hydrogen 1; Pi-System; Oxidation potential; Cations; Aromatic compound; Chemical synthesis; Silver I
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/jo800343f

The design and synthesis of a new dipyridyl ligand with appended phenanthryl moieties is described. On addition of increments of silver(I) trifluoromethanesulfonate to a solution of the ligand, the phenanthryl protons shift upfield in the 1H NMR spectrum, suggesting that the phenanthrenes π-stack on coordination of silver(I). In accord with this, the oxidation potential decreased from 1.74 to 1.55 V on complexation of silver(I). The π-stacking was confirmed with the single-crystal X-ray structure of a palladium(II) coordination complex.