TY - JOUR
T1 - Synthesis, characterization, and quantum chemistry local chemical reactivity description of new phosphorylated derivatives of piperazine
AU - González-González, Stephany
AU - Franco-Pérez, Marco
AU - Jardínez, Christiaan
AU - Cariño-Moreno, Jorge Jairo
AU - Ramírez-Sotelo, María Guadalupe
AU - Zamudio-Medina, Angel
N1 - Publisher Copyright:
© 2023 Taylor & Francis Group, LLC.
PY - 2023
Y1 - 2023
N2 - We report a fast, safe, and efficient procedure for the synthesis of phosphorylated derivatives of piperazines through a multicomponent reaction (MCR) strategy. Our key reagents were the piperazines 1-(2-methoxyphenyl) piperazine and 3-(4- (2-methoxyphenyl) piperazin-1-yl) propan-1-amine which reacted with five different phosphorous chlorides. A total of ten new derivatives were obtained, all confirmed by NMR spectroscopy (1H, 13C, and 31P) and mass spectrometry. Then, the reactivity profile of our new compounds was characterized through the new theoretical framework of the Local Electronic Temperature of Atoms in Molecules (LT-AIMs), from which we identified the most reactive sites of each of our derivatives. Furthermore, some of the quantities defined within this context were used to reproduce trends observed in our NMR records. A brief discussion about the advantages of performing a combined experimental and theoretical chemical characterization of recently synthesized compounds is also presented, particularly for those compounds with potential therapeutic features.
AB - We report a fast, safe, and efficient procedure for the synthesis of phosphorylated derivatives of piperazines through a multicomponent reaction (MCR) strategy. Our key reagents were the piperazines 1-(2-methoxyphenyl) piperazine and 3-(4- (2-methoxyphenyl) piperazin-1-yl) propan-1-amine which reacted with five different phosphorous chlorides. A total of ten new derivatives were obtained, all confirmed by NMR spectroscopy (1H, 13C, and 31P) and mass spectrometry. Then, the reactivity profile of our new compounds was characterized through the new theoretical framework of the Local Electronic Temperature of Atoms in Molecules (LT-AIMs), from which we identified the most reactive sites of each of our derivatives. Furthermore, some of the quantities defined within this context were used to reproduce trends observed in our NMR records. A brief discussion about the advantages of performing a combined experimental and theoretical chemical characterization of recently synthesized compounds is also presented, particularly for those compounds with potential therapeutic features.
KW - DFT
KW - Phosphoramidate
KW - phosphorous chlorides
KW - piperazine derivatives
KW - quantum chemistry
UR - http://www.scopus.com/inward/record.url?scp=85152268688&partnerID=8YFLogxK
U2 - 10.1080/10426507.2023.2193404
DO - 10.1080/10426507.2023.2193404
M3 - Artículo
AN - SCOPUS:85152268688
SN - 1042-6507
VL - 198
SP - 693
EP - 703
JO - Phosphorus, Sulfur and Silicon and the Related Elements
JF - Phosphorus, Sulfur and Silicon and the Related Elements
IS - 8
ER -