77302-53-5Relevant academic research and scientific papers
Charge-Assisted Halogen Bonding in Bromo- and Iodophenylpyridinium Chlorides
Kassl, Christopher J.,Swenson, Dale C.,Pigge, F. Christopher
, p. 4571 - 4580 (2015/09/15)
Ten N-halophenylpyridinium salts (halogen = Br or I) with chloride (and in one case iodide) counterions have been prepared and structurally characterized in order to examine the degree of solid state halogen bonding exhibited in these systems. N-Halophenylpyridinium salts are easily synthesized from existing pyridines, and the cationic pyridinium group is expected to increase the halogen bond donor ability of attached halophenyl moieties. Halide anions functioning as halogen bond acceptors facilitate formation of charge-assisted halogen bonds. All five substrates featuring iodophenyl or diiodophenyl substituents displayed the expected halogen bonding interactions. In several cases halide ion acceptors were also engaged in complementary hydrogen bonding interactions with C-H groups of pyridinium rings and O-H groups of water solvates. Halogen bond donors containing a diiodophenyl group formed either an extended network or discrete supramolecular macrocyclic constructs through ArI...Cl-...IAr bridging interactions. Significantly fewer and weaker halogen bonding interactions were observed in crystals of N-bromophenylpyridinium salts. The attenuation of halogen bonding in these substrates is attributed to the inability of the activated bromoarene halogen bond donors to compete with hydrogen bond donors (C-H/O-H residues) for the halide anion. (Chemical Equation Presented).
Efficient synthesis of various 4-tosyloxy-2-substituted phenols using pyridinium salt-supported [hydroxy(tosyloxy)iodo]benzene reagent
Yang, Bing,Zhang, Jizhen,Zhao, Dejian,Wang, Yazhen,Jia, Hongbin
, p. 930 - 932 (2013/09/02)
A novel pyridinium salt-supported [hydroxy(tosyloxy)-iodo]benzene (HTIB) reagent (N-{4-[hydroxy(tosyloxy)iodo]-phenyl}pyridinium hexafluorophosphate) was prepared via Zincke's reaction. The conjugated HTIB was an effective reagent for tosyloxylation of phenolic aromatic rings with an electron-withdrawing substitute at the ortho-position. The reagent can be easily regenerated in high yield and reused three times without any decrease in activity.
An efficient ultrasonic-assisted synthesis of imidazolium and pyridinium salts based on the Zincke reaction
Zhao, Sanhu,Xu, Xiaoming,Zheng, Lu,Liu, Hai
experimental part, p. 685 - 689 (2011/02/23)
A mild and efficient method has been developed using ultrasound irradiation for the synthesis of imidazolium and pyridinium salts based on the Zincke reaction. Tertiary nitrogen nucleophiles such as pyridines and imidazoles can be alkylated with primary amine by simply using their ammonium form Zincke salts. In almost all cases, a clear yield increase results and a dramatic reduction of the reaction time accompanied by an improved quality of the products occurs.
