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‘‘Click” analytics for ‘‘click” chemistry – A simple method for calibration–free evaluation of online NMR spectra

  • Driven mostly by the search for chemical syntheses under biocompatible conditions, so called "click" chemistry rapidly became a growing field of research. The resulting simple one-pot reactions are so far only scarcely accompanied by an adequate optimization via comparably straightforward and robust analysis techniques possessing short set-up times. Here, we report on a fast and reliable calibration-free online NMR monitoring approach for technical mixtures. It combines a versatile fluidic system, continuous-flow measurement of 1H spectra with a time interval of 20 s per spectrum, and a robust, fully automated algorithm to interpret the obtained data. As a proof-of-concept, the thiol-ene coupling between N-boc cysteine methyl ester and allyl alcohol was conducted in a variety of non-deuterated solvents while its time-resolved behaviour was characterized with step tracer experiments. Overlapping signals in online spectra during thiol-ene coupling could be deconvoluted with a spectralDriven mostly by the search for chemical syntheses under biocompatible conditions, so called "click" chemistry rapidly became a growing field of research. The resulting simple one-pot reactions are so far only scarcely accompanied by an adequate optimization via comparably straightforward and robust analysis techniques possessing short set-up times. Here, we report on a fast and reliable calibration-free online NMR monitoring approach for technical mixtures. It combines a versatile fluidic system, continuous-flow measurement of 1H spectra with a time interval of 20 s per spectrum, and a robust, fully automated algorithm to interpret the obtained data. As a proof-of-concept, the thiol-ene coupling between N-boc cysteine methyl ester and allyl alcohol was conducted in a variety of non-deuterated solvents while its time-resolved behaviour was characterized with step tracer experiments. Overlapping signals in online spectra during thiol-ene coupling could be deconvoluted with a spectral model using indirect hard modeling and were subsequently converted to either molar ratios (using a calibrationfree approach) or absolute concentrations (using 1-point calibration). For various solvents the kinetic constant k for pseudo-first order reaction was estimated to be 3.9 h-1 at 25 °C. The obtained results were compared with direct integration of non-overlapping signals and showed good agreement with the implemented mass balance.zeige mehrzeige weniger

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Metadaten
Autoren/innen:Aleksandra Michalik-Onichimowska, Simon KernORCiD, Jens Riedel, Ulrich Panne, R. King, Michael MaiwaldORCiD
Dokumenttyp:Zeitschriftenartikel
Veröffentlichungsform:Verlagsliteratur
Sprache:Englisch
Titel des übergeordneten Werkes (Englisch):Journal of Magnetic Resonance
Jahr der Erstveröffentlichung:2017
Organisationseinheit der BAM:P Präsidium
1 Analytische Chemie; Referenzmaterialien
1 Analytische Chemie; Referenzmaterialien / 1.4 Prozessanalytik
1 Analytische Chemie; Referenzmaterialien / 1.9 Chemische und optische Sensorik
P Präsidium / PST Präsidiale Stabsstelle
Veröffentlichende Institution:Bundesanstalt für Materialforschung und -prüfung (BAM)
Verlag:Elsevier Inc.
Verlagsort:Oxford
Jahrgang/Band:277
Erste Seite:154
Letzte Seite:161
DDC-Klassifikation:Naturwissenschaften und Mathematik / Chemie / Analytische Chemie
Freie Schlagwörter:Automated Data Evaluation; Click Chemistry; Online NMR Spectroscopy; Process Analytical Technology; Reaction Monitoring; Thiol-ene click chemistry
Themenfelder/Aktivitätsfelder der BAM:Analytical Sciences
Analytical Sciences / Zerstörungsfreie Prüfung und Spektroskopie
Analytical Sciences / Sensorik
DOI:https://doi.org/10.1016/j.jmr.2017.02.018
URN:urn:nbn:de:kobv:b43-393232
URL:http://www.sciencedirect.com/science/article/pii/S1090780717300575
URL:http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcAuth=Alerting&SrcApp=Alerting&DestApp=WOS&DestLinkType=FullRecord;UT=WOS:000399861500020
Verfügbarkeit des Volltexts:Volltext-PDF für die Öffentlichkeit verfügbar ("Open Access")
Lizenz (Deutsch):License LogoCreative Commons - CC BY-NC-ND - Namensnennung - Nicht kommerziell - Keine Bearbeitungen 4.0 International
Datum der Freischaltung:13.03.2017
Referierte Publikation:Ja
Datum der Eintragung als referierte Publikation:18.05.2017
Schriftenreihen ohne Nummerierung:Wissenschaftliche Artikel der BAM