A study of the structure and the conformational preferences of nine- and ten-membered rings of the corresponding pyrazolo[1,5-a][6,1]benzodiazonine and pyrazolo[1,5-a][7,1]benzodiazecine skeletons have been performed via dynamic NMR (variable temperature experiments), B3LYP/6-31G(d) DFT calculations and single-crystal X-ray diffraction analysis. The experimental values found for energy barrier to enantiomerisation due to ring inversion revealed high conformational stability of the nine-membered ring compared to the corresponding ten-membered one.
Structural and conformational study of pyrazolobenzodiazonine and pyrazolobenzodiazecine skeletons / L. De Benassuti, G. Molteni, A. Ponti, T. Recca, R. Soave. - In: TETRAHEDRON LETTERS. - ISSN 0040-4039. - 56:24(2015 Jun 10), pp. 3842-3846. [10.1016/j.tetlet.2015.04.093]
Structural and conformational study of pyrazolobenzodiazonine and pyrazolobenzodiazecine skeletons
L. De BenassutiPrimo
;G. Molteni
;T. ReccaPenultimo
;
2015
Abstract
A study of the structure and the conformational preferences of nine- and ten-membered rings of the corresponding pyrazolo[1,5-a][6,1]benzodiazonine and pyrazolo[1,5-a][7,1]benzodiazecine skeletons have been performed via dynamic NMR (variable temperature experiments), B3LYP/6-31G(d) DFT calculations and single-crystal X-ray diffraction analysis. The experimental values found for energy barrier to enantiomerisation due to ring inversion revealed high conformational stability of the nine-membered ring compared to the corresponding ten-membered one.File | Dimensione | Formato | |
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