Conclusions
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1.
The reversible replacement of methanol by methylate ion in the equatorial plane of the copper complex of N-salicylidene-S-valine has been studied spectrophotometrically; study has also been made of the kinetics of the MeO− ion-catalyzed racemization of the S-valine fragment of this complex in methanol solution at 25°C.
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2.
Pyridine and N-salicylidene-S-valine form a mixed complex with copper ions, the kinetic CH-acidity of this complex being higher than that of copper N-salicylidene-S-valinate.
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3.
N-2-Pyridinecarbonyl-2-aminobenzaldehyde has been synthesized and its Schiff base with S-valine used as ligand in a copper complex. Under the action of MeO−, the S-valine fragment of this complex racemizes 90 times more rapidly than the S-valine fragment of copper N-salicylidene-S-valinate.
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V. M. Belikov, Yu. N. Belokon', V. A. Karginov, N. S. Martinkova, and M. B. Saporovskaya, Izv. Akad. Nauk SSSR, Ser. Khim.,1976, 1277.
M. Ando and S. Emoto, Bull. Chem. Soc. Jpn.,42, 2624, 2628 (1969).
G. N. Weinstein, M. J. O'Connor, and R. H. Holm, Inorg. Chem.,9, 2104 (1970).
P. Pfeiffer, W. Offerman, and H. Werner, J. Prakt. Chem.,159, 313 (1942).
Yu. K. Yur'ev, Practical Operations in Organic Chemistry [in Russian], Izd-vo Mosk. Unta (1946), p. 57.
A. Weissberger, ed., Organic Solvents, Wiley (1955).
A. Albert and E. Serjeant, Ionization Constants for Acids and Bases, Methven (1962).
M. B. Saporovskaya, E. A. Paskonova, S. B. Nikitina, S. V. Vitt, and V. M. Belikov, Izv. Akad. Nauk SSSR, Ser. Khim.,1974, 676.
H. Fujimaki, J. Oonishi, F. Muto, A. Nakahara, and Y. Komijama, Bull. Chem. Soc. Jpn.,44, 31 (1971).
M. H. West and J. I. Legg. J. Am. Chem. Soc.,98, 6945 (1976).
R. B. Martin, Metal Ions in Biological Systems, (H. Sigel, ed.), Bekker, Inc., New York (1974), p. 129.
E. W. Wilson and R. B. Martin, Inorg. Chem.,10, 1197 (1971).
M. C. Lim, E. Sinn, and R. B. Martin, Inorg. Chem.,15, 807 (1976).
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 10, pp. 2276–2283, October, 1978.
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Belokon', Y.N., Belikov, V.M., Maksakov, V.A. et al. Amino acids as CH-acids 17. Increase in the amino acid α-proton mobility in Schiff base copper complexes with pyridine or N-2-pyridinecarbonyl-2′-aminobenzaldehyde ligands. Russ Chem Bull 27, 2014–2020 (1978). https://doi.org/10.1007/BF00946517
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DOI: https://doi.org/10.1007/BF00946517