This article is cited in 4 papers

Communications

trans-2-(Azaarylsulfanyl)cyclohexanol derivatives as potential pH-triggered conformational switches

M. R. Ruyonga, O. Mendoza, V. V. Samoshin

Department of Chemistry, University of the Pacific, Stockton, California, USA

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.

Language: English

DOI: 10.1016/j.mencom.2019.09.005

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