STERIC ACCELERATION OF REDUCTIVE DESULFONATION OF 1,8-NAPHTHALENEDISULFONATE BY AN NADH MODEL COMPOUND

Article abstract of DOI:10.1016/S0040-4039(01)81863-3

1,8-Naphthalenedisulfonate was reductively desulfonated by N-benzyl-1,4-dihydronicotinamide, whereas no desulfonation was observed for the 1,6-isomer.The high reactivity of the 1,8-isomer is attributed to the steric-strain that enforces the shift of the initial state with the sp²-carbon close to the transition state with the sp³-carbon.