Inter- and intramolecular Mitsunobu reaction and metal complexation study: synthesis of S-amino acids derived chiral 1,2,3,4-tetrahydroquinoxaline, benzo-annulated [9]-N3 peraza, [12]-N4 peraza-macrocycles

阅读量：

作者：

展开

摘要：

Substituted 1,2,3,4-tetrahydroquinoxaline, benzo-annulated unsymmetrical chiral [9]-N(3) peraza, and [12]-N(4) peraza-macrocycles have been synthesized employing an inter- and intramolecular Mitsunobu reaction from an amino acid derived common synthetic intermediate 3. The metal complexation study of these macrocycles has been investigated by UV-visible spectroscopic technique with binding constant (K(b)) value 1.84 × 10(3) dm(3) mol(-1) using the Benesi-Hildebrand equation and a Gibbs free energy (ΔG) -19.4 kJ mol(-1) at 35 °C for 14d with Co(2+). The binding properties of the metal were dependent on the structure of polyaza-macrocycles that were confirmed by the DFT optimized structure of two macrocycles. A detailed investigaton of UV-visible spectra of macrocycles and their complete interpretation with the help of TD-DFT along with the frontier molecular orbital calculations are presented.

展开

关键词：

HAN Fei idea contradiction tragedy

DOI：

10.1039/c1ob06304a

被引量：

年份：

2012