Conclusions
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1.
IR spectroscopy has been used to study intermolecular and intramolecular hydrogen bonding in certain phosphadepsipeptides.
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2.
In the condensed phase, these compounds associate through the formation of intermolecular hydrogen bonds in a process involving participation of the COOH and NH groups.
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3.
In solution, it is only those compounds which contain open COOH groups which undergo appreciable association; the remaining compounds form intramolecular hydrogen bonds in dilute solution, the bonding process involving NH group participation.
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Literature cited
K. Mislow and M. Reban, Selected Problems in Sterochemistry [Russian translation], Mir (1970).
J. L. Mateoz and D. J. Cram, J. Am. Chem. Soc.,81, 2756 (1959).
M. J. (I.) Kabachnik, T. A. Mastryukova, E. J. (I.) Fedin, M. S. Veisberg, L. L. Morosov, P. V. Petrovsky (Petrovskii), and A. E. Schipov (Shipov), Tetrahedron,32, 1719 (1976).
M. I. Kabachnik, E. I. Fedin, L. L. Morozov, M. S. Vaisberg, P. V. Petrovskii, A. E. Shipov, and T. A. Mastryukova, Izv. Akad. Nauk SSSR, Ser. Khim., 67 (1976).
D. Hadzi and N. Kabilarov, J. Chem. Soc., A, 439 (1966).
E. I. Matrosov, E. N. Tsvetkov, D. I. Lobanov, R. A. Malevannaya, and M. I. Kabachnik, Zh. Obshch. Khim.,42, 1218 (1972).
E. I. Matrosov, E. N. Tsvetkov, R. A. Malevannaya, and M. I. Kabachnik, Zh. Obshch. Khim.,42, 1695 (1972).
L. J. Bellamy, Infrared Spectra of Complex Molecules, Halsted Press (1975).
T. Gramstad, Spectrochim. Acta,19, 497 (1963).
T. Gramstad and W. J. Fuylevik, Acta Chem. Scand.,15, 2368 (1962).
R. R. Shagiddulin, I. P. Lipatova, L. I. Vachugova, and S. A. Samartseva, Dokl. Akad. Nauk SSSR,202, 617 (1972).
S. Rengaraja and K. Berlin, J. Org. Chem.,37, 3304 (1972).
C. C. Costain and J. M. Dowling, J. Chem. Phys.,32, 158 (1960).
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 11, pp. 2491–2497, November, 1977.
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Matrosov, E.I., Mastryukova, T.A., Shipov, A.É. et al. Hydrogen bonding and association of certain phosphadepsipeptides. Russ Chem Bull 26, 2310–2314 (1977). https://doi.org/10.1007/BF00958717
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DOI: https://doi.org/10.1007/BF00958717