TY - JOUR A1 - Tepper, Christina A1 - Haberhauer, Gebhard T1 - Toward unidirectional switches: 2-(2-Hydroxyphenyl)pyridine and 2-(2-methoxyphenyl)pyridine derivatives as pH-triggered pivots JF - Beilstein Journal of Organic Chemistry PY - 2012/// VL - 8 SP - 977 EP - 985 SN - 1860-5397 DO - 10.3762/bjoc.8.110 PB - Beilstein-Institut JA - Beilstein J. Org. Chem. UR - https://doi.org/10.3762/bjoc.8.110 KW - CD spectroscopy KW - chirality KW - molecular modeling KW - molecular switches KW - unidirectional movements N2 - The pH-induced switching process of 2-(2-hydroxyphenyl)pyridine and 2-(2-methoxyphenyl)pyridine derivatives was investigated with the help of UV spectroscopy. Quantum chemical calculations at the B3LYP/6-31G* level of theory were performed to show that in the case of 2-(2-methoxyphenyl)-3-methylpyridine and 2-(2-hydroxyphenyl)-3-methylpyridine the rotation during the switching process proceeds unidirectionally at the molecular level. If a 2-(2-methoxyphenyl)pyridine derivative is fixed to a chiral cyclopeptidic scaffold, a unidirectional progress of the rotation is achieved macroscopically. ER -