NMR and Quantum-Chemical Studies of Electrostatically Stabilized 1-(N,N-Substituted-aminiomethyl)spirobi [3-oxo(2,5-dioxa-1-silacyclopentan)]ates (ES-Silanates)

Alons Lends; E. Olszewska; Sergejs Beļakovs; N. Erchak; E. Liepiņš

NMR and Quantum-Chemical Studies of Electrostatically Stabilized 1-(N,N-Substituted-aminiomethyl)spirobi [3-oxo(2,5-dioxa-1-silacyclopentan)]ates (ES-Silanates)

Heteroatom Chemistry 2015
Alons Lends, E. Olszewska, Sergejs Beļakovs, N. Erchak, E. Liepiņš

1-(N,N-substituted-aminiomethyl)spirobi[3-oxo(2,5-dioxa-1-silacyclopentan)]ates were investigated using NMR, X-ray, and quantum-chemical methods. The free activation parameters for the inversion of “ammonium-amine nitrogen” and the chirality change at the pentacoordinated silicon were determined by dynamic NMR spectroscopy. The latter proceeds via the dissociation of Si[BOND]O bonds. The results were confirmed by quantum-chemical calculations, the experimental observation of cross-peaks in 2D-EXSY NMR spectra, and the spirocycle exchange reactions. Transition pathways between the different diastereomers in solution were analyzed.

Keywords
1-(N,N-Substituted-aminiomethyl)spirobi [3-oxo(2,5-dioxa-1-silacyclopentan)]ates
DOI
10.1002/hc.21203
Hyperlink
http://onlinelibrary.wiley.com/doi/10.1002/hc.21203/abstract

Lends, A., Olszewska, E., Beļakovs, S., Erchak, N., Liepiņš, E. NMR and Quantum-Chemical Studies of Electrostatically Stabilized 1-(N,N-Substituted-aminiomethyl)spirobi [3-oxo(2,5-dioxa-1-silacyclopentan)]ates (ES-Silanates). Heteroatom Chemistry, 2015, Vol.26, No.1, pp.12-28. e-ISSN 1098-1071. Available from: doi:10.1002/hc.21203

Publication language
English (en)