Naslov
Utilization of sym -tetrazines as guanidine delivery cycloaddition reagents. An experimental and computational study

Autori
Briš, Anamarija ; Murata, Yasujiro ; Hashikawa, Yoshifumi ; Margetić, Davor

Izvornik
Journal of molecular structure (0022-2860) 1272 (2023); 134207, 11

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
Tetrazines ; Cycloadditions ; Diels-Alder reactions ; Calculations

Sažetak
Novel 2-pyridyl- sym -tetrazines (1, 2, 4, 5- tetrazines) bearing a guanidine functional group were synthetized. Their cycloaddition properties were studied in inverse electron demand [4 + 2] cycloaddition reactions with norbornenes and C 60 fullerene. Experimental results were corroborated with density functional the- ory calculations (DFT) with M06-2X functional. Guanidine sym- tetrazines were found to be reactive to- wards strained polycyclic alkenes (norbornenes), whereas reactions with C 60 fullerene were less success- ful. Estimated activation energies are in full accordance with experimental findings. Further computa- tional studies of a series of tetrazine derivatives indicated their cycloaddition reactivity and potential synthetic utility.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

POVEZANOST RADA