Photochemistry of N-substituted salicylic acid amides

作者：Pozdnyakov I P; Storozhok N M^*; Medyanik N P; Krekov S A; Borisenko V E; Krysin A P; Plyusnin V F; Grivin V P

来源：Russian Chemical Bulletin, 2015, 64(6): 1319-1326.

DOI：10.1007/s11172-015-1012-5

• salicylic acid amide
• photolysis
• phenyl radical
• recombination
• IR and UV spectroscopy
• hydrogen bond
• deuteration

The products of photolysis of N-substituted salicylic acid amides, viz., 2-hydroxy-3-tert-butyl-5-ethylbenzoic acid N-(4-hydroxy-3,5-di-tert-butylphenyl)amide (1) and 2-hydroxybenzoic acid N-[3-(4-hydroxy-3,5-di-tert-butylphenyl)prop-1-yl]amide (2), in heptane were studied by optical spectroscopy and stationary and nanosecond laser photolysis (Nd: YAG laser, 355 nm). It was shown by the method of partial deuteration of amides 1 and 2 that they exist in both the unbound state and as complexes with intraand intermolecular hydrogen bond. Amides 1 and 2 are subjected to photolysis, which results in the formation of a triplet state and phenoxyl radicals ROaEuro cent presumably due to the absorption of the second photon by the excited singlet state. The formation of radical products due to N-H bond ionization was not observed. The main channel of decay of the triplet state and radicals ROaEuro cent is triplet-triplet annihilation and recombination (k (r) a parts per thousand 2.3aEuro cent 10(8) L mol(-1) s(-1)), respectively. The UV irradiation of compounds 1 and 2 leads to the excitation of the amide groups, and no formation of radical products due to N-H bond ionization was observed.

• 出版日期2015-6