Abstract:
A series of trans-2-(azaarylsulfanyl)cyclohexanol derivatives, structurally similar to previously studied trans-2-amino-cyclohexanols, were synthesized through epoxide ring opening under basic conditions with sodium tetraborate as a catalyst. 1H NMR spectroscopy was used to elucidate the conformational equilibrium in various solvents and its acid-induced change due to stabilization of the conformer with the azaarylsulfanyl and hydroxy groups in equatorial position by an intramolecular hydrogen bond and electrostatic interactions.
Citation:
M. R. Ruyonga, O. Mendoza, V. V. Samoshin, “trans-2-(Azaarylsulfanyl)cyclohexanol derivatives as potential pH-triggered conformational switches”, Mendeleev Commun., 29:5 (2019), 495–497
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https://www.mathnet.ru/eng/mendc1568
https://www.mathnet.ru/eng/mendc/v29/i5/p495
This publication is cited in the following 4 articles:
Megan L. Qualls, Ruhani Sagar, Jinchao Lou, Michael D. Best, “Demolish and Rebuild: Controlling Lipid Self-Assembly toward Triggered Release and Artificial Cells”, J. Phys. Chem. B, 125:47 (2021), 12918
M. R. Ruyonga, V. V. Samoshin, “Conformational energy (A-value) of the 4-phenyl-1,2,3-triazolyl group”, Mendeleev Commun., 31:5 (2021), 609–611
Jinchao Lou, Michael D. Best, “Strategies for altering lipid self-assembly to trigger liposome cargo release”, Chemistry and Physics of Lipids, 232 (2020), 104966
Mulinde R. Ruyonga, Oscar Mendoza, Michael Browne, Vyacheslav V. Samoshin, “Exploration of trans‐2‐(azaarylsulfanyl)‐cyclohexanols as potential pH‐triggered conformational switches”, J of Physical Organic Chem, 33:7 (2020)
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