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Rotational Barriers of Substituted BIPHEP Ligands: A Comparative Experimental and Theoretical Study
- 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 kJmol(-1) and were found to be in excellent agreement with the calculated data. The root-mean-square deviations are 7.3 kJmol(-1) for the B3LYP functional and 11.3 kJmol(-1) for the M06-2X method.
Author details: | Golo Storch, Frank Maier, Pablo WessigORCiDGND, Oliver Trapp |
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DOI: | https://doi.org/10.1002/ejoc.201600836 |
ISSN: | 1434-193X |
ISSN: | 1099-0690 |
Title of parent work (English): | European journal of organic chemistry |
Publisher: | Wiley-VCH |
Place of publishing: | Weinheim |
Publication type: | Article |
Language: | English |
Year of first publication: | 2016 |
Publication year: | 2016 |
Release date: | 2020/03/22 |
Tag: | Biaryls; Density functional calculations; Enantioselectivity; Liquid chromatography; P ligands; Rotational barriers |
Volume: | 22 |
Number of pages: | 4 |
First page: | 5123 |
Last Page: | 5126 |
Funding institution: | European Research Council (ERC) [258740]; German Fonds der Chemischen Industrie |
Organizational units: | Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie |
Peer review: | Referiert |