Photochemistry of N-substituted salicylic acid amides

Photochemistry of N-substituted salicylic acid amides Full article

Journal

Russian Chemical Bulletin
ISSN: 1066-5285 , E-ISSN: 1573-9171

Output data

Year: 2015, Volume: 64, Number: 6, Pages: 1319-1326 Pages count : 8 DOI: 10.1007/s11172-015-1012-5

Tags

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

Authors

Pozdnyakov I.P. ¹ , Storozhok N.M. ² , Medyanik N.P. ² , Krekov S.A. ³ , Borisenko V.E. ³ , Krysin A.P. ⁴ , Plyusnin V.F. ¹ , Grivin V.P. ¹

Affiliations

1	Institute of Chemical Kinetics and Combustion, Siberian Branch, Russian Academy of Sciences, 3 ul. Institutskaya, 630090, Novosibirsk, Russian Federation
2	Tyumen State Medical University, Ministry of Health of the Russian Federation, 54 ul. Odesskaya, 625023, Tyumen, Russian Federation
3	Tyumen State University, 10 ul. Semakova, 625003, Tyumen, Russian Federation
4	Novosibirsk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences, 9 prosp. Akad. Lavrent´eva, 630090, Novosibirsk, Russian Federation

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.

Pozdnyakov I.P. , Storozhok N.M. , Medyanik N.P. , Krekov S.A. , Borisenko V.E. , Krysin A.P. , Plyusnin V.F. , Grivin V.P.
Photochemistry of N-substituted salicylic acid amides
Russian Chemical Bulletin. 2015. V.64. N6. P.1319-1326. DOI: 10.1007/s11172-015-1012-5 WOS Scopus РИНЦ

Поздняков И.П. , Сторожок Н.М. , Медяник Н.П. , Креков С.А. , Борисенко В.Е. , Крысин А.П. , Плюснин В.Ф. , Гривин В.П.
Фотохимия N-замещенных амидов салициловой кислоты
Известия Академии наук. Серия химическая.(RUSS CHEM B+). 2015. №6. С.1319. РИНЦ

Published print:	Jun 1, 2015
Published online:	Feb 27, 2016

Web of science	WOS:000371313900009
Scopus	2-s2.0-84959355289
Elibrary	26971388
OpenAlex	W2341992166