Conclusions
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1.
The geometrical structures of the chloroanhydrides of certain alkylsulfonic acids have been determined by study of vibrational and PMR spectra and measurements of dipole moments and Kerr constants. Increasing the size of the substituent at theα-carbon atom reduces the content of the conformer with trans orientation of the substituent relative to the phosphoryl group.
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2.
Comparison of the spectra of Cl2P(O)Alk and the spectra of complexes of these compounds with SnCl4, undissociated under the conditions of the present experiments, showed that band doubling in the 1250–1300 cm−1 region could not be entirely due to the establishment of a conformational equilibrium.
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3.
Free-atom interaction gives a satisfactory explanation of the geometrical structures established here.
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Literature cited
H. Gerding and J. W. Maarsen, Rec. Trav. Chim.,76, 481 (1957).
C. Christol and H. Christol, J. Chim. Phys. Chim.-Phys. Biol.,62, 246 (1965).
E. Steger and M. Kuntze, Spectrochim. Acta,23A, 2189 (1967).
A. N. Pudovik, I. Ya. Kuramshin, A. B. Remizov, A. A. Muratova, and R. A. Manapov, Zh. Obshch. Khim.,44, 44 (1974); A. I. Fishman and A. B. Remizov, Opt. Spektrosk.,38, 858 (1975).
R. R. Shagidullin, I. I. Vandyukova, and I. A. Nuretdinov, Izv. Akad. Nauk SSSR, Ser. Khim., 801 (1976).
J. B. Robert and J. D. Roberts, J. Am. Chem. Soc.,94, 4902 (1972).
C. H. Bushweller and J. A. Brunelle, J. Am. Chem. Soc.,95, 5949 (1973).
A. Kinnear and E. Perren, J. Chem. Soc., 3437 (1952).
F. W. Huffman, T. C. Simmons, and L. J. Glunz III, J. Am. Chem. Soc.,79, 3570 (1957).
A. V. Iogansen, Opt. Spektrosk.,5, 813 (1964).
A. F. Vasil'ev, Zh. Prikl. Spektrosk.,6, 485 (1967); O. A. Raevskii, R. R. Shagidullin, and L. E. Petrova, Izv. Akad. Nauk SSSR, Ser. Khim., 1426 (1971); O. A. Raevskii, V. D. Akamsin, F. G. Khalitov, and Yu. A. Donskaya, Izv. Akad. Nauk SSSR, Ser. Khim., 2451 (1972).
O. A. Raevskii, Vopr. Stereokhim.,5, 69 (1976); O. A. Raevsky, Yu. A. Donskaya, F. G. Khalitov, E. L. Vorkunova, and Ya. A. Levin, Phosphorus,5, 241 (1975).
O. A. Raevskii, F. G. Khalitov, and Yu. A. Donskaya, Izv. Akad. Nauk SSSR, Ser. Khim., 513 (1972); O. A. Raevskii, Yu. A. Donskaya, A. Ya. Kessel', L. V. Nesterov, and M. A. Pudovik, Izv. Akad. Nauk SSSR, Ser. Khim., 536 (1973); A. N. Pudovik, A. A. Muratova, I. Ya. Kuramshin, and É. G. Yarkova, Zh. Obshch. Khim.,42, 317 (1972).
O. A. Raevskii, A. N. Vereshchagin, N. G. Mumzhieva, T. A. Zyablikova, and N. A. Aleksandrova, J. Mol. Structure,38, 299 (1977); V. A. Naumov and V. N. Semashko, Zh. Strukt. Khim.,12, 317 (1971).
J. W. Emsley, J. Feeney, and L. H. Sutcliffe, High Resolution NMR Spectroscopy [Russian translation], Mir (1968),1, p. 158.
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 3, pp. 614–621, March, 1978.
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Raevskii, O.A., Mumzhieva, N.G., Zyablikova, T.A. et al. Hindered internal rotation in the dichloroanhydrides of certain alkylphosphonic acids. Russ Chem Bull 27, 528–534 (1978). https://doi.org/10.1007/BF00923931
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DOI: https://doi.org/10.1007/BF00923931