Abstract
The equilibrium torsion angles of 2-arylpyrroles in the liquid and solid phases were estimated by UV spectroscopy. In solution, compounds containing no substituents in positions 1, 3, and 2′ possess an average torsion angle of 24°, those containing one substituent have an angle of 29°, and in the case of two and three substituents, the angles are 53° and 65°, respectively. Phase transitions lead to flattening of the molecules in almost all cases. The average torsion angles in the compounds with no substituents in positions 1, 3, and 2′ decrease by ≈5° on passing from the gas to the liquid state and by ≈25° on going from the liquid to the solid state. The geometric parameters of 2-arylpyrroles with one or two substituents in positions 1, 3, and 2′ are less sensitive to phase transitions, while trisubstituted derivatives even retain their equilibrium conformations upon phase transitions.
Similar content being viewed by others
References
A. Almenningen, O. Bastiansen, L. Fernholt, B. N. Cyvin, S. J. Cyvin, and S. Samdal,J. Mol. Struct., 1985,128, 59.
A. Proutiere, D. Legoff, M. Chabanel, and E. Megnassan,J. Mol. Struct., 1988,178, 49.
H. Suzuki,Electronic Absorption Spectra and Geometry of Organic Molecules, Academic Press, New York, 1967, 568 pp.
J. Trotter,Acta Crystallogr., 1961,14, 1135.
C. P. Brock and R. P. Minton,J. Am. Chem. Soc., 1989,111, 4586.
J. D. McKinney and P. Singh,Acta Crystallogr. 1988,C44, 558.
A. Skancke,Acta Chem. Scand., 1970,24, 1389.
L. Lunazzi, F. Salvetti, and C. A. Veracini,J. Chem. Soc. Perkin Trans. 2, 1976, 1796.
G. J. Visser, G. J. Heers, J. Wolters, and A. Vos,Acta Crystallogr., 1968,B24, 467.
H. Lumbroso, D. M. Bertin, and F. Marschner,J. Mol. Struct., 1988,178, 187.
A. V. Afonin, M. V. Sigalov, S. E. Korostova, S. A. Aliev, A. V. Vashchenko, and B. A. Trofimov,Magn. Res. Chem., 1990,28, 580.
C. W. Fong,Aust. J. Chem., 1980,33, 1763.
A. F. Ermikov, V. K. Turchaninov, K. B. Petrushenko, A. I. Vokin, S. E. Korostova, L. A. Ostroukhova, and Yu. L. Frolov,Zh. Obshch. Khim., 1988,58, 450 [J. Gen. Chem. USSR, 1988,58 (Engl. Transl.)].
V. K. Turchaninov, A. F. Ermikov, S. E. Korostova, and V. A. Shagun,Zh. Obshch. Khim., 1989,59, 79 [J. Gen. Chem. USSR, 1989,59 (Engl. Transl.)].
V. K. Turchaninov, A. I. Vokin, D.-S. D. Toryashinova, A. F. Ermikov, K. B. Petrushenko, and S. E. Korostova,Izv. Akad. Nauk, Ser. Khim., 1993, 319 [Russ. Chem. Bull., 1993,42, 275 (Engl. Transl.)].
V. K. Turchaninov, A. I. Vokin, D.-S. D. Toryashinova, S. E. Korostova,Izv. Akad. Nauk, Ser. Khim., 1993, 869 [Russ. Chem. Bull., 1993,42, 822 (Engl. Transl.)].
J. Del Bene and H. H. Jaffe,J. Chem. Phys., 1968,48, 1807.
R. C. Bingham, M. J. S. Dewar, and D. H. Lo,J. Am. Chem. Soc., 1975,97, 1285.
B. A. Trofimov and A. I. Mikhaleva,N-Vinilpirroly [N-Vynilpyrroles], Nauka, Novosibirsk, 1984, 262 pp. (in Russian).
B. A. Trofimov, inPyrroles. Part Two: The Synthesis, Reactivity, and Physical Properties of Substituted Pyrroles, Ed. R. Alan Jones, J. Willey and Sons, New York, 1992, 131.
J. N. Murrell,The Theory of the Electronic Spectra of Organic Molecules, Academic Press, New York, London, 1964, 238 pp.
M. Bavia, F. Bertinelli, C. Taliani, and C. Zauli,Mol. Phys., 1976,31, 479.
L. Serrano-Andres, M. Merchan, I. Nebot-Gil, B. O. Roos, and M. Fulscher,J. Am. Chem. Soc., 1993,115, 6184.
J. O. Williams,Chem. Phys. Lett. 1976,42, 171.
Atlas spektrov aromaticheskikh i geterotsiklicheskikh soedinenii [Atlas of the Spectra of Aromatic and Heterocyclic Compounds] Ed. V. A. Koptyug, Nauka, Novosibirsk, 1981, No. 21, 102 pp.
Author information
Authors and Affiliations
Additional information
Deceased.
Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1472–1479, August, 1997.
Rights and permissions
About this article
Cite this article
Turchaninov, V.K., Vokin, A.I. & Korostova, S.E. The effect of the physical state on the equilibrium conformation of 2-arylpyrroles. Russ Chem Bull 46, 1407–1414 (1997). https://doi.org/10.1007/BF02505676
Received:
Revised:
Issue Date:
DOI: https://doi.org/10.1007/BF02505676