Abstract
Dipole moment studies have revealed that furan-2-carboxylic acid esters exist in nonpolar solvents predominantly in O,O-cis-conformations. The dipole moment value of a 2-furoate ester depends on the electronic and steric effects of the substituents in the alcohol portion of the ester. The complex nature of the v C=O band region in the IR spectra of 2-furoates is due primarily to the appearance of resonance absorption bands.
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Literature Cited
V. N. Sheinker, A.D. Garnovskii, and O. A. Osipov, Usp. Khim., 50, 632 (1981).
L. M. Nazarova and Ya. K. Syrkin, Izv. Akad. Nauk SSSR, Ser. Khim., No. 1, 35 (1949).
M. L. Martin, J. C. Rose, G. J. Martin, and P. Fouranary, Tetrahedron Lett., No. 39, 3407 (1970).
D. J. Chadwick, J. Chambers, G. D. Meakins, and R. L. Snowden, Chem. Commun., No. 12, 625 (1971).
D. J. Chadwick, J. Chambers, G. D. Meakins, and R. L. Snowden, J. Chem. Soc., Perkin Trans., 2, No. 1, 1 (1976).
R. M. Minyaev, V. I. Minkin, and V. N. Sheinker, Zh. Org. Khim., 11, 1950 (1975).
C. Regenet, J. P. Morizur, and H. Lumbŕoso, Bull. Soc. Chim. France, No. 2, 361 (1964).
O. A. Isipov, V. I. Minkin, and A. D. Garnovskii, Handbook of Dipole Moments [in Russian], Vyssh. Shkola, Moscow (1971), p. 138, 160.
V. S. Pustovarov, O. E. Shelepin, Z. N. Nazarova, and L. P. Bobova, VINITI 04.07.72, No. 51100-72, Rostov-on-Don, Rostov State University.
D. J. Chadwick and G. D. Meakins, Chem. Commun., No. 12, 637 (1970).
L. P. Gardenina, L. A. Kotorlenko, and A. F. Rekasheva, Zh. Prikl. Khim., 10, 329 (1969).
L. de la Campa, J. Fernandez Bertran, and R. Fagundo, Rev. CENIC Cienc. Fis., 10, 295 (1979).
Z. N. Nazarova, L. D. Babeshkina, and O. E. Shelepin, VINITI 0.6.06.73, No. 6232-73, Rostov-on-Don, Rostov State University.
A. R. Katritzky and A. P. Embler, Physical Methods in the Chemistry of Heterocyclic Compounds [Russian translation], Khimiya, Moscow, Leningrad (1966), p. 504.
A. A. Ponomarev, Synthesis and Reactions of Furan Compounds [in Russian], Saratov University Press, Saratov (1964).
S. C. Srivastava and P. Charandas, J. Chem. Phys., 30, 816 (1959).
B. V. Ioffe, R. R. Kostikov, and V. V. Razin, Physical Methods in the Structure Determination of Organic Molecules [in Russian], Leningrad State University Press, Leningrad (1976).
V. I. Minkin, O. A. Osipov. and Yu. A. Zhdanov, Dipole Moments in Organic Chemistry [in Russian], Khimiya, Leningrad (1968), p. 75.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1605–1610, December, 1987.
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Gumennyi, V.I. Structure and properties of furan-2-carboxylic acid esters. 1. Dipole moments and IR spectra. Chem Heterocycl Compd 23, 1288–1292 (1987). https://doi.org/10.1007/BF00472248
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DOI: https://doi.org/10.1007/BF00472248