Physical properties and chemical constitution. Part XXVIII. Pyridine derivatives was written by Kyte, Colin T.;Jeffery, George H.;Vogel, Arthur I.. And the article was included in Journal of the Chemical Society in 1960.SDS of cas: 27876-24-0 This article mentions the following:
Purified samples of the following were prepared: pyridine, 2-, 3-, and 4-alkyl (Me to n-heptyl), Ac, and CHO derivatives of pyridine, 2-, and 3-(hydroxymethyl)pyridine, alkyl (Me to heptyl) esters of picolinic, nicotinic, and isonicotinic acids, 2,3-, 2,6-, 2,5-, and 3,5-lutidine, dialkyl oxalates, and aliphatic aldehydes. Refractive indexes at 20° (C, D, F, G’ lines), densities, and surface tensions at 20°, 40°, 60°, and 85°, parachors, mol. refractivities, and mol. refraction coefficients for these compounds were determined and tabulated. The mean values for CH2 in parachors, mol. refractivities, and mol. refraction coefficients for mono- and dialkylpyridines, alkyl nicotinates, picolinates, and isonicotinates, as well as the corresponding constants for the 2-, 3-, and 4-pyridyl group, were measured. Ultraviolet and infrared spectra of the pyridine derivatives were taken. Pyridine was purified by the complex (C5H5N)2.ZnCl2.HCl followed by regeneration and fractionation. Thus, 80 ml. pyridine was added with stirring to 68 g. ZnCl2 and 42 ml. concentrated HCl in 200 ml. absolute EtOH, the mixture cooled, the precipitate washed with EtOH, and air-dried, m. 153° (absolute EtOH). Also α-picoline was purified through (2-MeC5H4)2.ZnCl2.HCl, m. 118.5-19.5° (absolute EtOH). γ-Picoline was purified by preparing (4-MeC5H4N)2.ZnCl2.HCl, m. 130-0.5° (absolute EtOH), regenerating the base, treating with urea to remove 2,6-lutidine, and fractionally freezing in a special apparatus (description given). Impurities were removed from β-picoline by treatment with Ac2O-phthalic anhydride according to a modified procedure of Riethof, et al. (CA 40, 54337). The lutidines were usually purified by fractional distillation, conversion to a solid derivative, regeneration of the base, and fractional freezing. Preparation of the urea complexes of 2,3- and 2,6-lutidine, of 2,4-lutidine-HCl, and PhOH-2,5-lutidine complex, m. 57.5° (petr. ether), was described. Fractional distillation and freezing gave pure 3,5-lutidine. The 2-, 3-, and 4-alkylpyridines were prepared by alkylation of the corresponding picolines with alkyl chlorides in the presence of NaNH2 (Chichibabin, CA 30, 82089, 32, 49848). Only monoalkylation occurred with α-picoline and colloidal NaNH2 in xylene at 140°, but with γ-picoline at 0°, about 36% mono- and 20 % dialkylated product formed. Formation of dialkylated γ-picoline was avoided by alkylation in liquid NH3. Satisfactory monoalkylation of β-picoline required liquid NH3 solutions of NaNH2 prepared in situ. sec-Alkylpyridines were readily prepared in liquid NH3 by using 2 equivalents NaNH3 and an alkyl chloride. The preferred method of preparing pure monoethylpyridines was the Wolff-Kishner reduction of the Ac compounds 4-Alkylpyridines (Et to Bu) were prepared from pyridine by a modified Wibaut-Arens synthesis (CA 35, 58945; 37, 50635). Similarly, 4-ethyl-3-methylpyridine was prepared from β-picoline. KMnO4 oxidation of purified picolines gave pure pyridine monocarboxylic acids whose lower alkyl esters were prepared with HCl catalyst, the higher ones with H2SO4 catalyst, or by treating the acid chloride hydrochloride with the alc. EtOAc was condensed with Et pyridinecarboxylates by NaOEt or NaH in dry xylene followed by acid hydrolysis of the oxo ester (not isolated) to give the acetylpyridines. Com. pyridine aldehydes were purified by passing SO2 into 50 g. aldehyde in 250 ml. O-free H2O to complete precipitation of the adduct. The adduct was refluxed under N in 200 ml. 17% HCl to complete solution, neutralized with NaHCO3, and extracted with Et2O. The extracts were dried and distilled under N. The com. 2-, and 3-(hydroxymethyl)pyridines were purified by fractional distillation In the experiment, the researchers used many compounds, for example, 4-Hexylpyridine (cas: 27876-24-0SDS of cas: 27876-24-0).
4-Hexylpyridine (cas: 27876-24-0) belongs to pyridine derivatives. Pyridine has a dipole moment and a weaker resonant stabilization than benzene (resonance energy 117 kJ·molâ? in pyridine vs. 150 kJ·molâ? in benzene). Pyridine derivatives are also useful as small-molecule α-helix mimetics that inhibit protein-protein interactions, as well as functionally selective GABA ligands.SDS of cas: 27876-24-0