The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Tetrazole analogs of pyridinecarboxylic acids》. Authors are McManus, J. M.; Herbst, Robert M..The article about the compound:5-(4-Pyridyl)-1H-tetrazolecas:14389-12-9,SMILESS:C1(C2=NN=NN2)=CC=NC=C1).Name: 5-(4-Pyridyl)-1H-tetrazole. Through the article, more information about this compound (cas:14389-12-9) is conveyed.
The isomeric 5-tetrazolylpyridines were prepared as analogs of the pyridinecarboxylic acids by interaction of the cyanopyridines with NH3 (I). Interaction of 2,6-dicyanopyridine (II) and I gave the tetrazole analog (III) of dipicolinic acid. Hydrogenation of the tetrazolylpyridines gave the corresponding 5-tetrazolylpiperidines, the analogs of the several isomeric piperidinecarboxylic acids. 2-Cyanopyridine (26 g.), 20 g. AcOH, and 22 g. NaN3 refluxed 4 days in 100 ml. BuOH, heated 2 days with a further 5 g. NaN3 and 10 g. AcOH (in other experiments 3- and 4-day heating periods gave approx. the same yields), the mixture diluted with 300 ml. H2O, the BuOH removed, the solution acidified, and the product separated gave 33.4 g. 5-(2-pyridyl)tetrazole (IV), m. 211-11.5° (decomposition) (H2O). Similarly, 3-cyanopyridine and I gave 91% 5-(3-pyridyl)tetrazole (V), m. 234-5° (decomposition) (H2O). Likewise, 4-cyanopyridine and I gave 93% 5-(4-pyridyl)tetrazole (VI), m. 253-4° (decomposition). II (27.5 g.) in 100 ml. BuOH refluxed 2 days with 38.2 g. NaN3 and 38 ml. AcOH then 2 days with 10 g. NaN3 and 20 ml. AcOH gave 45.6 g. III, m. 290° (decomposition)(H2O). IV (11 g.) in 150 ml. AcOH shaken 24 hrs. at 50 lb./sq. in. with 250 mg. PtO2 and H gave 10.5 g. 5-(2-piperidyl)tetrazole, m. 287° (decomposition); acetyl derivative m. 135.5-6.5° (H2O). For preparative purposes it was advantageous to form the acetyl derivative directly by hydrogenation of IV and after removal of the catalyst it was treated with Ac2O to give an over-all yield of 84%. V similarly hydrogenated gave an almost quant. yield of 5-(3-piperidyl)tetrazole, m. 296-7°(H2O); acetyl derivative m. 170-1° (iso-PrOH). VI also gave 86% 5-(4-piperidyl)tetrazole, prisms, not decomposing below 370°; acetyl derivative m. 156.5-7.5° (iso-PrOH).
In some applications, this compound(14389-12-9)Name: 5-(4-Pyridyl)-1H-tetrazole is unique.If you want to know more details about this compound, you can contact with the author or consult more relevant literature.
Reference:
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis—I. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis