Rotational barriers of substituted BIPHEP ligands

• Verfasst von: Storch, Golo [VerfasserIn]
• Verfasst von: Maier, Frank [VerfasserIn]
• Verfasst von: Trapp, Oliver [VerfasserIn]
• Titel: Rotational barriers of substituted BIPHEP ligands
• Titelzusatz: a comparative experimental and theoretical study
• Verf.angabe: Golo Storch, Frank Maier, Pablo Wessig, and Oliver Trapp
• E-Jahr: 2016
• Jahr: 23 August 2016
• Umfang: 4 S.
• Fussnoten: Gesehen am 19.05.2020
• Titel Quelle: Enthalten in: European journal of organic chemistry
• Ort Quelle: Weinheim : Wiley-VCH Verl., 1998
• Jahr Quelle: 2016
• Band/Heft Quelle: (2016), 30, Seite 5123-5126
• ISSN Quelle: 1099-0690
• DOI: doi:10.1002/ejoc.201600836
• Datenträger: Online-Ressource
• Sprache: eng
• Sach-SW: Biaryls
• Sach-SW: Density functional calculations
• Sach-SW: Enantioselectivity
• Sach-SW: Liquid chromatography
• Sach-SW: P ligands
• Sach-SW: Rotational barriers
• K10plus-PPN: 1698516304

Abstract

The interconversion barriers of 14 different 3,3?- and 5,5?-disubstituted tropos BIPHEP [2,2?-bis(diphenylphosphino)-1,1?-biphenyl] and BIPHEP(O) [2,2?-bis(diphenylphosphoryl)-1,1?-biphenyl] ligands were investigated by enantioselective dynamic high performance liquid chromatography (DHPLC) and DFT calculations using the B3LYP/6-31G* and M06-2X/6-31G* levels of theory. The experimentally determined enantiomerization barriers varied from 86.8 to 101.4 kJ?mol?1 and were found to be in excellent agreement with the calculated data. The root-mean-square deviations are 7.3 kJ?mol?1 for the B3LYP functional and 11.3 kJ?mol?1 for the M06-2X method.