| Angenommene Version Download ( PDF | 3MB) | Lizenz: Creative Commons Namensnennung-NichtKommerziell 3.0 de |
Highly Acidic N-Triflylphosphoramides as Chiral Brønsted Acid Catalysts: The Effect of Weak Hydrogen Bonds and Multiple Acceptors on Complex Structures and Aggregation
Hecht, Markus
, Dullinger, Philipp, Silva, Wagner
, Horinek, Dominik
und Gschwind, Ruth M.
(2024)
Highly Acidic N-Triflylphosphoramides as Chiral Brønsted Acid Catalysts: The Effect of Weak Hydrogen Bonds and Multiple Acceptors on Complex Structures and Aggregation.
Chemical Science 15, S. 9104-9111.
(Im Druck)
Veröffentlichungsdatum dieses Volltextes: 16 Mai 2024 06:50
Artikel
DOI zum Zitieren dieses Dokuments: 10.5283/epub.58272
Zusammenfassung
N-Triflylphosphoramides (NTPAs) represent an important catalyst class in asymmetric catalysis due to their multiple hydrogen bond acceptor sites and acidity, which is increased by several orders of magnitude compared to conventional chiral phosphoric acids (CPAs). Thus, NTPAs allow for several challenging transformations, which are not accessible with CPAs. However, detailed evidence on their ...
N-Triflylphosphoramides (NTPAs) represent an important catalyst class in asymmetric catalysis due to their multiple hydrogen bond acceptor sites and acidity, which is increased by several orders of magnitude compared to conventional chiral phosphoric acids (CPAs). Thus, NTPAs allow for several challenging transformations, which are not accessible with CPAs. However, detailed evidence on their hydrogen bonding situation, complex structures and aggregation is still lacking. Therefore, this study covers the hydrogen bonding behavior and structural features of binary NTPA/imine complexes compared to their CPA counterparts. Deviating from the single-well potential hydrogen bonds commonly observed in CPA/imine complexes, the NTPA/imine complexes exhibit a tautomeric equilibrium between two proton positions. Low-temperature NMR at 180 K supported by computer simulations indicate a OHN hydrogen bond between the phosphoramide oxygen and the imine, instead of the mostly proposed NHN H-bond. Furthermore, this study finds no evidence for the existence of dimeric NTPA/NTPA/imine complexes as previously suggested for CPA systems, both synthetically and through NMR studies.
Alternative Links zum Volltext
Beteiligte Einrichtungen
Details
| Dokumentenart | Artikel | ||||
| Titel eines Journals oder einer Zeitschrift | Chemical Science | ||||
| Verlag: | Royal Society of Chemistry | ||||
|---|---|---|---|---|---|
| Band: | 15 | ||||
| Seitenbereich: | S. 9104-9111 | ||||
| Datum | 2024 | ||||
| Institutionen | Chemie und Pharmazie > Institut für Organische Chemie > Arbeitskreis Prof. Dr. Ruth Gschwind Chemie und Pharmazie > Institut für Physikalische und Theoretische Chemie > Lehrstuhl für Chemie IV - Physikalische Chemie (Solution Chemistry) > Prof. Dr. Dominik Horinek | ||||
| Identifikationsnummer |
| ||||
| Dewey-Dezimal-Klassifikation | 500 Naturwissenschaften und Mathematik > 540 Chemie | ||||
| Status | Im Druck | ||||
| Begutachtet | Ja, diese Version wurde begutachtet | ||||
| An der Universität Regensburg entstanden | Ja | ||||
| URN der UB Regensburg | urn:nbn:de:bvb:355-epub-582720 | ||||
| Dokumenten-ID | 58272 |
Downloadstatistik
Downloadstatistik