On the Physicochemical Properties of Pyridohelicenes

0427612 - ÚOCHB 2015 RIV DE eng J - Journal Article
Vacek Chocholoušová, Jana - Vacek, Jaroslav - Andronova, Angelina - Míšek, Jiří - Songis, Olivier - Šámal, Michal - Stará, Irena G. - Meyer, M. - Bourdillon, M. - Pospíšil, Lubomír - Starý, Ivo
On the Physicochemical Properties of Pyridohelicenes.
Chemistry - A European Journal. Roč. 20, č. 3 (2014), s. 877-893. ISSN 0947-6539. E-ISSN 1521-3765
R&D Projects: GA AV ČR IAA400550916; GA ČR GA203/09/1802; GA ČR GA203/09/0705; GA MŠMT MEB021139; GA MŠMT ME09019; GA MŠMT ME09020
Institutional support: RVO:61388963 ; RVO:61388955
Keywords : basicity * chirality * cyclic voltammetry * density functional calculations * helical structures * helicenes
Subject RIV: CC - Organic Chemistry
Impact factor: 5.731, year: 2014

A comprehensive study on the physicochemical properties of a series of mono- and diaza[5]helicenes as well as mono- and diaza[6]helicenes is reported. Through the use of both computational and experimental methods, these helically chiral pyridohelicenes with the nitrogen atom(s) in various positions are characterised according to their inversion barriers, protonation constants and redox potentials. By using DFT calculations, kinetic measurements, UV/Vis titrations, cyclic voltammetry and EPR spectroscopy, a self-contained picture of their behaviour under conventional treatment by heat, acids and oxidising/reducing agents is provided.
Permanent Link: http://hdl.handle.net/11104/0233158