Synthesis and anion-selective complexation of homobenzylic tripodal thiourea derivatives was written by Hisaki, Ichiro;Sasaki, Shin-Ichi;Hirose, Keiji;Tobe, Yoshito. And the article was included in European Journal of Organic Chemistry in 2007.Synthetic Route of C15H15N3 The following contents are mentioned in the article:
Cryptand- and tripod-type thiourea derivatives I [R = n-Bu (II), Bn (III), Ph (IV), p-nitrophenyl (V)] which have binding functionalities at the homobenzylic positions, were synthesized as possible neutral receptors toward anions with an expectation that the three binding sites work cooperatively to bind an anion selectively. 1H NMR spectroscopic monitoring of the titration of cryptand-type thiourea derivative with CH3CO2–, Cl–, and F– in CDCl2CDCl2 at 100 °C showed that the binding constants were considerably smaller than those of I, presumably owing to the presence of strong intramol. hydrogen bonding in cryptand-type thiourea derivatives Complexation constants of I with H2PO4–, CH3CO2–, Cl–, and Br– anions were evaluated by 1H NMR and/or UV/Vis spectroscopic anal. of the titration in DMSO. Though II and III undergo complexation with phosphate anion in a 1:1 stoichiometry, their association constants were not as large as simple reference compound, N,N’-dibenzyl thiourea, probably because of the steric hindrance around the binding sites and the large entropy cost for cooperative binding. IV exhibits complexation in a 1:2 stoichiometry with H2PO4– and CH3CO2–, whereas it forms 1:1 complexes with chloride and bromide anions because of the subtle balance between the steric hindrance and the binding ability. However, by increasing the acidity of the thiourea functionality, V exhibited remarkably enhanced binding ability and selectivity toward H2PO4– compared to those of reference compound, N-(4-nitrophenyl)-N’-(2-phenylethyl) thiourea, presumably through cooperative complexation of the three binding sites to the guest anion. This study involved multiple reactions and reactants, such as 2,2′,2”-(2,4,6-Trimethylbenzene-1,3,5-triyl)triacetonitrile (cas: 16144-65-3Synthetic Route of C15H15N3).
2,2′,2”-(2,4,6-Trimethylbenzene-1,3,5-triyl)triacetonitrile (cas: 16144-65-3) belongs to nitriles. Nitriles are polar, as indicated by high dipole moments. As liquids, they have high relative permittivities, often in the 30s. Alkyl nitriles are sufficiently acidic to undergo deprotonation of the C-H bond adjacent to the CN group.Strong bases are required, such as lithium diisopropylamide and butyl lithium. The product is referred to as a nitrile anion. Synthetic Route of C15H15N3
Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts