RT Journal Article
T1 Deciphering the degree of proton-transfer in pyrido-cyclophanes by chiroptical outcomes in non-aqueous solvents
A1 Álvarez García, Jonathan
A1 Rubio Pisabarro, Víctor
A1 García Río, Luis
A1 Cid, María Magdalena
K1 Proton transfer
K1 Chiral pyrido-cyclophanes
AB Proton transfer equilibria are of pivotal importance due to the role they play in a plethora of biological and phamaceutical processes. With the aim of explaining the relative position of the hydrogen to be transferred, we investigated the behavior of chiral pyrido-cyclophanes with different morphologies using circular dichroism in the presence of different acids in acetonitrile. The results showed that all three compounds underwent double protonation and formation of cascade ion-pairs, leading to the appearance of diagnostic signals in their ECD spectra. The presence of water fosters the crystallization of several intermediates that do not correspond to those in solution. By using Brønsted correlations, it was found that proton transfer from the acid to the pyridine occurred regardless of the acid's pKa
PB Royal Society of Chemistry
SN 2052-4129
YR 2023
FD 2023-09-18
LK https://hdl.handle.net/10347/44405
UL https://hdl.handle.net/10347/44405
LA eng
NO Álvarez-García, J., Rubio-Pisabarro, V., García Río, L., Cid, M.M. (2023). Deciphering the degree of proton-transfer in pyrido-cyclophanes by chiroptical outcomes in non-aqueous solvents. In: Org. Chem. Front., 2023,10, 5435-5442
NO Xunta de Galicia (EC431C 2021/41)
NO CESGA for allocation of HPC resources and Universidade de Vigo Structural analysis unit (CACTI)
DS Minerva
RD 24 abr 2026