Rotational Isomers, Intramolecular Hydrogen Bond, and IR Spectra of o-Vinylphenol Homologs
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The ν(OH) stretching-mode bands in solution IR spectra of five o-vinylphenol (o-VPh) homologs in the slightly polar solvents CCl4 and n-hexane were studied. Several rotamers with free OH groups were found in solutions of o-VPh and its methyl-substituted derivatives in n-hexane. The proportion of rotamers in o-VPh homologs with intramolecular hydrogen bonds (IHBs) O–H...π varied from 22 to 97% in the gas and cyclohexane according to B3LYP/cc-pVTZ calculations. The theoretically estimated effective enthalpies –ΔH of their IHBs varied in the range 0.20–2.24 kcal/mol.
Keywords
o-vinyl-, o-propenyl-, and o-butenylphenols IR spectrum ν(OH) stretching-mode bands density functional rotamer intramolecular hydrogen bond, enthalpyPreview
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References
- 1.O. R. Wulf, U. Liddel, and S. B. Hendricks, J. Am. Chem. Soc., 58, No. 11, 2287– 2293 (1936).CrossRefGoogle Scholar
- 2.A. W. Baker and A. T. Shulgin, J. Am. Chem. Soc., 80, No. 10, 5358–5363 (1958).CrossRefGoogle Scholar
- 3.A. W. Baker and A. T. Shulgin, Spectrochim. Acta, 20, No. 1, 153–158 (1964).ADSCrossRefGoogle Scholar
- 4.M. Oki and H. Iwamura, Bull. Chem. Soc. Jpn., 33, No. 5, 681–684 (1960).CrossRefGoogle Scholar
- 5.M. Oki and H. Iwamura, Bull. Chem. Soc. Jpn., 39, No. 3, 470–476 (1966).CrossRefGoogle Scholar
- 6.M. Oki and H. Iwamura, Bull. Chem. Soc. Jpn., 33, No. 6, 717–721 (1960).CrossRefGoogle Scholar
- 7.D. V. Berdyshev, V. P. Glazunov, and V. L. Novikov, Izv. Ross. Akad. Nauk, Ser. Khim., 57, No. 3, 499–508 (2008) [Russ. Chem. Bull., Int. Ed., 57, No. 3, 510–519 (2008)].Google Scholar
- 8.R. J. Capon, E. L. Ghisalberti, and P. R. Jefferies, Aust. J. Chem., 35, No. 12, 2583–2587 (1982).CrossRefGoogle Scholar
- 9.A. Sato, T. Shindo, N. Kasanuki, and K. Hasegawa, J. Nat. Prod., 52, No. 5, 975–981 (1989).CrossRefGoogle Scholar
- 10.M. Aknin, T. L.-A. Dayan, A. Rudi, Y. Kashman, and E. M. Gaydou, J. Agric. Food Chem., 47, No. 10, 4175–4177 (1999).CrossRefGoogle Scholar
- 11.A. V. Danks and R. Hodges, Aust. J. Chem., 27, No. 7, 1603–1606 (1974).CrossRefGoogle Scholar
- 12.M. S. R. Nair and S. T. Carey, Tetrahedron Lett., 20, No. 35, 3233–3236 (1979).CrossRefGoogle Scholar
- 13.L. Kopanski, G.-R. Li, H. Besl, and W. Steglich, Liebigs Ann. Chem., No. 9, 1722–1729 (1982).Google Scholar
- 14.G. W. van Eijk and H. J. Roeijmans, Exp. Mycol., 8, No. 3, 266–268 (1984).CrossRefGoogle Scholar
- 15.W. J. Dale and H. E. Hennis, J. Am. Chem. Soc., 80, No. 14, 3645–3649 (1958).CrossRefGoogle Scholar
- 16.B. B. Corson, W. J. Heintzelman, L. H. Schwartzman, H. E. Tiefenthal, R. J. Lokken, J. E. Nickels, G. R. Atwood, and F. J. Pavlik, J. Org. Chem., 23, No. 4, 544–549 (1958).CrossRefGoogle Scholar
- 17.B. A. M. Oude-Alink, A. W. K. Chan, and C. D. Gutsche, J. Org. Chem., 38, No. 11, 1993–2001 (1973).CrossRefGoogle Scholar
- 18.G. Casiraghi, G. Casnati, G. Sartori, and L. Bolzoni, J. Chem. Soc., Perkin Trans. I, 2027–2029 (1979).Google Scholar
- 19.V. P. Glavunov, D. V. Berdyshev, N. N. Balaneva, O. S. Radchenko, and V. L. Novikov, Zh. Prikl. Spektrosk., 81, No. 1, 19–25 (2014) [V. P. Glavunov, D. V. Berdyshev, N. N. Balaneva, O. S. Radchenko, and V. L. Novikov, J. Appl. Spectrosc., 81, No. 1, 15–21 (2014)].Google Scholar
- 20.P. J. Stephens, F. J. Devlin, C. F. Chabalowski, and M. J. Frisch, J. Phys. Chem., 98, No. 45, 11623–11627 (1994).CrossRefGoogle Scholar
- 21.S. Miertus, E. Scrocco, and J. Tomasi, Chem. Phys., 55, No. 1, 117–129 (1981).ADSCrossRefGoogle Scholar
- 22.Gaussian 03, Revision D.01, Gaussian Inc., Wallingford СТ (2004).Google Scholar
- 23.M. Sibaev and D. L. Crittenden, J. Phys. Chem. A, 119, No. 52, 13107–13112 (2015).CrossRefGoogle Scholar
- 24.V. P. Glazunov and D. V. Berdyshev, Zh. Prikl. Spektrosk., 79, No. 5, 689–700 (2012) [V. P. Glazunov and D. V. Berdyshev, J. Appl. Spectrosc., 79, No. 5, 675–686 (2012)].Google Scholar
- 25.D. V. Berdyshev, V. P. Glazunov, and V. L. Novikov, Zh. Prikl. Spektrosk., 76, No. 5, 666–676 (2009) [D. V. Berdyshev, V. P. Glazunov, and V. L. Novikov, J. Appl. Spectrosc., 76, 630–640 (2009)].Google Scholar
- 26.D. V. Berdyshev, N. N. Balaneva, V. P. Glazunov, and V. L. Novikov, Izv. Ross. Akad. Nauk, Ser. Khim., 63, No. 9, 1976–(2014) [D. V. Berdyshev, N. N. Balaneva, V. P. Glazunov, and V. L. Novikov, Russ. Chem. Bull., 63, No. 9, 1976–1985(2014)].Google Scholar
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