ROTATIONAL ISOMERS, INTRAMOLECULAR HYDROGEN BOND, AND IR SPECTRA OF o-VINYLPHENOL HOMOLOGUES
Abstract
The n(ОН) stretching mode bands in IR spectra of the solutions of five o-vinylphenol homologues (o-VPh) in CCl4 and n-hexane low polarity solvents were studied. Several rotamers with a free OH group were found in the solution of o-VPh and its methyl substituted in n-hexane. According to the calculations by the B3LYP/cc-pVTZ method, the proportion of rotamers in o-VPh homologues with intramolecular hydrogen bond О-Н…p (IHB) varies from 22 to 97% in the gas and in the cyclohexane medium. Theoretical values of the effective enthalpy -ΔН of its IHB vary in the range 0.20-2.24 kcal/mol.
Keywords
о-винил-, о-пропенил- и о-бутенилфенолы,
инфракрасный спектр,
валентные колебания О-Н-связи,
функционал плотности,
ротамер,
внутримолекулярная водородная связь,
энтальпия,
o-vinyl-, o-propenyl-, and o-butenylphenols,
infrared spectrum,
n(ОН) stretching mode bands,
density functional,
rotamer,
intramolecular hydrogen bond,
enthalpy
About the Authors
V. P. Glazunov
G. B. Elyakov Pacific Institute of Bioorganic Chemistry, Far-Eastern Branch of the Russian Academy of Sciences
Russian Federation
Russian Federation
D. V. Berdyshev
G. B. Elyakov Pacific Institute of Bioorganic Chemistry, Far-Eastern Branch of the Russian Academy of Sciences
Russian Federation
Russian Federation
N. N. Balaneva
G. B. Elyakov Pacific Institute of Bioorganic Chemistry, Far-Eastern Branch of the Russian Academy of Sciences
Russian Federation
Russian Federation
O. S. Radchenko
G. B. Elyakov Pacific Institute of Bioorganic Chemistry, Far-Eastern Branch of the Russian Academy of Sciences
Russian Federation
Russian Federation
V. L. Novikov
G. B. Elyakov Pacific Institute of Bioorganic Chemistry, Far-Eastern Branch of the Russian Academy of Sciences
Russian Federation
Russian Federation
References
1. O. R. Wulf, U. Liddel, S. B. Hendricks. J. Am. Chem. Soc., 58, N 11 (1936) 2287-2293
2. A. W. Baker, A. T. Shulgin. J. Am. Chem. Soc., 80, N 10 (1958) 5358-5363
3. A. W. Baker, A. T. Shulgin. Spectrochim. Acta, 20, N 1 (1964) 153-158
4. M. Oki, H. Iwamura. Bull. Chem. Soc. Jpn., 33, N 5 (1960) 681-684
5. M. Oki, H. Iwamura. Bull. Chem. Soc. Jpn., 39, N 3 (1966) 470-476
6. M. Oki, H. Iwamura. Bull. Chem. Soc. Jpn., 33, N 6 (1960) 717-721
7. Д. В. Бердышев, В. П. Глазунов, В. Л. Новиков. Изв. РАН. Сер. хим., 57, № 3 (2008) 499-508 [Russ. Chem. Bull., Int. Ed., 57, N 3 (2008) 510-519]
8. R. J. Capon, E. L. Ghisalberti, P. R. Jefferies. Aust. J. Chem., 35, N 12 (1982) 2583-2587
9. A. Sato, T. Shindo, N. Kasanuki, K. Hasegawa. J. Nat. Prod., 52, N 5 (1989) 975-981
10. M. Aknin, T. L.-A. Dayan, A. Rudi, Y. Kashman, E. M. Gaydou. J. Agric. Food. Chem., 47, N 10 (1999) 4175-4177
11. A. V. Danks, R. Hodges. Aust. J. Chem., 27, N 7 (1974) 1603-1606
12. M. S. R. Nair, S. T. Carey. Tetrahedron Lett., 20, N 35 (1979) 3233-3236
13. L. Kopanski, G.-R. Li, H. Besl, W. Steglich. Liebigs Ann. Chem., N 9 (1982) 1722-1729
14. G. W. van Eijk, H. J. Roeijmans. Exp. Mycol., 8, N 3 (1984) 266-268
15. W. J. Dale, H. E. Hennis. J. Am. Chem. Soc., 80, N 14 (1958) 3645-3649
16. B. B. Corson, W. J. Heintzelman, L. H. Schwartzman, H. E. Tiefenthal, R. J. Lokken, J. E. Nickels, G. R. Atwood, F. J. Pavlik. J. Org. Chem., 23, N 4 (1958) 544-549
17. B. A. M. Oude-Alink, A. W. K. Chan, C. D. Gutsche. J. Org. Chem., 38, N 11 (1973) 1993-2001
18. G. Casiraghi, G. Casnati, G. Sartori, L. Bolzoni. J. Chem. Soc., Perkin Trans. I (1979) 2027-2029
19. В. П. Глазунов, Д. В. Бердышев, Н. Н. Баланева, О. С. Радченко, В. Л. Новиков. Журн. прикл. спектр., 81, № 1 (2014) 19-25 [V. P. Glazunov, D. V. Berdyshev, N. N. Balaneva, O. S. Radchenko, V. L. Novikov. J. Appl. Spectr., 81 (2014) 15-21]
20. P. J. Stephens, F. J. Devlin, C. F. Chabalowski, M. J. Frisch. J. Phys. Chem., 98, N 45 (1994) 11623-11627
21. S. Miertus, E. Scrocco, J. Tomasi. Chem. Phys., 55, N 1 (1981) 117-129
22. Gaussian 03, Revision D.01, Gaussian Inc., Wallingford СТ (2004)
23. M. Sibaev, D. L. Crittenden. J. Phys. Chem. A, 119, N 52 (2015) 13107-13112
24. В. П. Глазунов, Д. В. Бердышев. Журн. прикл. спектр., 79, № 5 (2012) 689-700 [V. P. Glazunov, D. V. Berdyshev. J. Appl. Spectr., 79 (2012) 675-686]
25. Д. В. Бердышев, В. П. Глазунов, В. Л. Новиков. Журн. прикл. спектр., 76, № 5 (2009) 666-676 [D. V. Berdyshev, V. P. Glazunov, V. L. Novikov. J. Appl. Spectr., 76 (2009) 630-640]
26. Д. В. Бердышев, Н. Н. Баланева, В. П. Глазунов, В. Л. Новиков. Изв. РАН. Сер. хим., 63, № 9 (2014) 1976-1985 [D. V. Berdyshev, N. N. Balaneva, V. P. Glazunov, V. L. Novikov. Russ. Chem. Bull., 63, N 9 (2014) 1976-1985]
Review
For citations:
Glazunov V.P., Berdyshev D.V., Balaneva N.N., Radchenko O.S., Novikov V.L. ROTATIONAL ISOMERS, INTRAMOLECULAR HYDROGEN BOND, AND IR SPECTRA OF o-VINYLPHENOL HOMOLOGUES. Zhurnal Prikladnoii Spektroskopii. 2018;85(1):14-26. (In Russ.)
Views:
312
Email this article 