Synthesis, Structure and Chemical Properties of 1-Oxydopyridinediazonium Sulfonates

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Рұқсат жабық Тек жазылушылар үшін

Аннотация

The products of diazotization of 2-, 3-, and 4-aminopyridin-1-oxides in the presence of TsOH, TfOH, and camphorsulfonic acid were investigated by IR, NMR, X-ray diffraction analysis, ESI/MS and MS2 spectroscopy, and B3LYP/aug-cc-pVDZ. The structures of the products and their stability during storage depend on the type of the starting aminopyridine. 4-Aminopyridin-1-oxide reacts to give stable diazonium sulfonates, and the 2-aminoisomer gives [1,2,3,5]oxotriazol[5,4-a]pyridinium-2 sulfonates. All products readily undergo reactions typical for diazonium salts. By the B3LYP/aug-cc-pVDZ method it was determined that 4-diazonium-pyridinium-1-oxide and benzoldiazonium cation have the highest stability in the series of diazonium cations of pyridine, pyridine-1-oxide and benzoldiazonium cation.

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Авторлар туралы

E. Krasnokutskaya

National Research Tomsk Polytechnic University

Хат алмасуға жауапты Автор.
Email: eak@tpu.ru
ORCID iD: 0000-0002-6292-7974
Ресей, 30, Lenin Ave., Tomsk, 634050

A. Sanzhiev

National Research Tomsk Polytechnic University

Email: eak@tpu.ru
ORCID iD: 0000-0002-9464-0281
Ресей, 30, Lenin Ave., Tomsk, 634050

K. Erin

National Research Tomsk Polytechnic University

Email: eak@tpu.ru
ORCID iD: 0009-0002-9137-4747
Ресей, 30, Lenin Ave., Tomsk, 634050

A. Bondarev

Altai State University

Email: eak@tpu.ru
ORCID iD: 0000-0002-8707-2394
Ресей, 61, Lenin Ave., Barnaul, 656049

A. Potapov

Nikolaev Institute of Inorganic Chemistry of the Siberian Branch of Russian Academy of Sciences

Email: eak@tpu.ru
ORCID iD: 0000-0003-2360-7473
Ресей, 3, Acad. Lavrentiev Ave., Novosibirsk, 630090

V. Filimonov

National Research Tomsk Polytechnic University

Email: eak@tpu.ru
ORCID iD: 0000-0003-4729-8871
Ресей, 30, Lenin Ave., Tomsk, 634050

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1. JATS XML
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2. Scheme 1

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3. Table 1_Fig. 1

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4. Table 1_Fig. 2

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5. Table 1_Fig. 3

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6. Table 1_Fig. 4

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7. Table 1_Fig. 5

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8. Table 1_Fig. 5

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9. Scheme 2

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10. Scheme 3

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11. Fig. 1. ESI/MS spectrum of C5H4NO-4-N2+ TfO- 4a in the positive desrfe ionisation mode. A = [C5H4NON2+], m/z = 122.04; B = [C5H4NO+], m/z = 94.03; cluster cations Cn = [C5H4NON2+]n+1[TfO-]n. m/z for cations C1...C6 = 393.02; 664.1; 935.00; 1205.99; 1476.97; 1747.96

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12. Scheme 4

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13. Scheme 5

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14. Table 3_Fig. 1

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15. Table 3_Fig. 2

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16. Table 3_Fig. 3

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17. Table 3_Fig. 4

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18. Table 3_Fig. 5

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19. Table 3_Fig. 6

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20. Table 3_Fig. 7

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21. Table 3_Fig. 8

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22. Table 3_Fig. 9

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23. Table 3_Fig. 10

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24. Fig. 2. Structure of 5-methyl[1,2,3,5]oxotriazol[5,4-a]pyridinium-2 triflate 7a from PCA data: (a) asymmetric crystal structure unit, hydrogen atoms not shown; (b) intermolecular packing interactions, view along the b-axis

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25. Scheme 6

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26. Fig. 3. MS2 spectrum of pyridinium cation 1a (122.04 m/z) for the salts: a) C5H4NO-2-N2+ TfO- (6a), b) C5H4NO-2-N2+ TsO- (6b), c) C5H4NO-2-N2+ CamphSO3- (6c)

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27. Scheme 7

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