Excited state intramolecular proton transfer in o-tosylaminobenzaldehyde.
Excited state intramolecular proton transfer (ESIPT) in o-tosylaminobenzaldehyde has been investigated. According to quantum-chemical calculations ESIPT in o-tosylaminobenzaldehyde is barrierless. Product of ESIPT undergoes efficient nonradiative deactivation caused by internal rotation of C(H)OH-group. The solvent orientational relaxation in anionic form of o-tosylaminobenzaldehyde was detected. The mechanism of anionic form fluorescence quenching at the addition of the base in a protic solvent is proposed. It consists in the intermolecular proton transfer from the protonated base to oxygen atom of aldehyde group followed by the internal rotation of C(H)OH-group.
Chemistry Department, Moscow State University, 119991, Moscow, Russia.
Mikhail N
MN
Khimich
Leonid D
LD
Popov
Anatoly S
AS
Burlov
Boris M
BM
Uzhinov
D001547:Benzaldehydes / Q000737:chemistry*; D004579:Electron Transport; D011522:Protons; D013050:Spectrometry, Fluorescence
C572516:2-tosylaminobenzaldehyde; D001547:Benzaldehydes; D011522:Protons