Abstract:
The relative thermodynamic stability of unionized and zwitterionic forms of α-phosphino-α-amino acids is governed by the substituent R at the nitrogen atom, namely, (het)aryl substituents favour the formation of the unionized form RHNCH(PPh2)COOH, while in the case of alkyl analogues the zwitterions RH2N+CH(PPh2)COO− predominate. The experimentally observed trends have been supported by quantum-chemical calculations. The synthesis and X-ray crystal structure analysis of a new unionized α-phosphino-α-amino acid [α-diphenylphosphino-N-(2-methoxycarbonylphenyl) glycine] are reported.
Citation:
O. S. Soficheva, A. A. Nesterova, A. B. Dobrynin, E. M. Zueva, J. W. Heinicke, O. G. Sinyashin, D. G. Yakhvarov, “The effect of N-substituent on the relative thermodynamic stability of unionized and zwitterionic forms of α-diphenylphosphino-α-amino acids”, Mendeleev Commun., 30:4 (2020), 516–518
Linking options:
https://www.mathnet.ru/eng/mendc1243
https://www.mathnet.ru/eng/mendc/v30/i4/p516
This publication is cited in the following 7 articles:
O. S. Soficheva, G. E. Bekmukhamedov, D. G. Yakhvarov, “Catalytic Synthesis of Butene-1 and Hexene-1 in the Homogeneous Oligomerization of Ethylene in the Presence of Nickel Complexes Based on N-Heteroaryl-Substituted α-Diphenylphosphinoglycines”, Kinet Catal, 65:1 (2024), 8
O. S. Soficheva, G. E. Bekmukhamedov, D. G. Yakhvarov, “Catalytic Synthesis of Butene-1 and Hexene-1 in the Homogeneous Oligomerization of Ethylene in the Presence of Nickel Complexes Based on N-Heteroaryl-Substituted α-Diphenylphosphinoglycines”, Kinetika i kataliz, 65:1 (2024), 12
I. F. Sakhapov, A. A. Kagilev, A. O. Kantyukov, I. K. Mikhailov, O. S. Sof'icheva, D. R. Islamov, Z. N. Gafurov, D. G. Yakhvarov, “Synthesis, Structure, and Electrochemical Properties of Cobalt Complex Based on N-(2,5-Bis(methoxycarbonyl)phenyl)-α-diphenylphosphorylglycinate”, Russ. J. Inorg. Chem., 68:9 (2023), 1257
I. F. Sakhapov, A. A. Kagilev, A. O. Kantyukov, I. K. Mikhailov, O. S. Soficheva, D. R. Islamov, Z. N. Gafurov, D. G. Yakhvarov, “Sintez, struktura i elektrokhimicheskie svoistva kompleksa kobalta na osnove N-(2,5-bis(metoksikarbonil)fenil)-α-difenilfosforilglitsinata”, Žurnal neorganičeskoj himii, 68:9 (2023), 1287
Dmitry V. Moiseev, Brian R. James, “Phospha-Mannich reactions of RPH2, R2PH, and R3P”, Phosphorus, Sulfur, and Silicon and the Related Elements, 197:4 (2022), 327
Alina A. Kagileva, Alexey A. Kagilev, Artyom O. Kantyukov, Zufar N. Gafurov, Il'yas F. Sakhapov, Giyjaz E. Bekmukhamedov, Khasan R. Khayarov, Ekaterina M. Zueva, Olga S. Soficheva, Dmitry G. Yakhvarov, “Influence of N- and P-substituents in N-aryl-phosphinoglycine ligands on the selectivity of Ni-catalysed ethylene oligomerization”, New J. Chem., 46:36 (2022), 17303
E. I. Musina, A. S. Balueva, A. A. Karasik, Organophosphorus Chemistry, 2022, 1
Contact us: