Synthesis and Structure of Silver Amino‐Arenesulfonates

Abstract

Treatment of a variety of zwitterionic amino‐arenesulfonic acids with silver oxide has resulted in the synthesis of seven new AgI amino‐arenesulfonates [Ag(O3SR)]∞ [R = o‐aminobenzyl (oAB) (1), m‐aminobenzyl (mAB) (2), 6‐amino‐3‐methoxybenzyl (6A3MB) (3), o‐aminonaphthyl (oAN) (4), 5‐aminonaphthyl (5AN) (5), 4‐amino‐3‐hydroxynaphthyl (4A3HN) (6) and 5‐isoquinolinyl (I) (7)]. This has allowed an exploration of their coordination chemistry, whereby we examine the impact of structural diversity in the anions: the position of the amino functionality on the arene moiety, inclusion of the N within a heterocycle and an increase in ring size from phenyl to naphthyl. The solid‐state structures of 1, 2 and two forms of 4, one with a coordinated water molecule, have been determined by X‐ray diffraction and are all polymeric. Analytical data is provided for two of the structurally known complexes: known silver p‐aminobenzenesulfonate 8 [Ag(O3SBAp)]∞ and AgI 2‐pyridinesulfonate [Ag(O3SP)]∞ (9). The composition of all nine complexes has been confirmed through NMR spectroscopy, MS‐ES+, FTIR and elemental analysis.

Synthesis and Characterisation of Bismuth(III) Aminoarenesulfonate Complexes and Their Powerful Bactericidal Activity against Helicobacter pylori

“…The target aminoarenesulfonato bismuth(III) compounds 1 – 9 were successfully prepared in a two‐step, one‐pot reaction (Scheme ), whereby the suite of silver(I) aminoarenesulfonates were generated in situ from treatment of the aminosulfonic acid with freshly prepared Ag 2 O13 in THF at room temperature (RT) 9. In the second step a THF solution of freshly sublimed [BiCl 3 ] was added.…”

“…were successfully prepared in a two-step, one-pot reaction (Scheme 1), whereby the suite of silver(I) aminoA C H T U N G T R E N N U N G arene-A C H T U N G T R E N N U N G sulfonates were generated in situ from treatment of the aminosulfonic acid with freshly prepared Ag 2 O [13] in THF at room temperature (RT). [9] In the second step a THF solution of freshly sublimed [BiCl 3 ] was added. A colour change in the reaction mixture from brown to cream generally indicated completion of the reaction.…”

“…However, all the Bi III complexes were soluble in DMSO, thereby allowing separation of the salts. Precipitation of the bismuth complexes from DMSO solution was subsequently achieved using either ethyl acetate (1)(2)(3)(4) or tert-butanol (5)(6)(7)(8)(9).…”

“…However, the bismuth(III) carboxylates thus produced were often contaminated with the more soluble alkali‐metal salt byproducts. These contaminants are unwanted when assessing new compounds for biological activity, and as such led us to synthesise and study the solid‐state structures of a series of silver(I) aminoarenesulfonates as precursors to their bismuth(III) analogues, the results of which have been reported elsewhere 9…”

“…These contaminants are unwanted when assessing new compounds for biological activity, and as such led us to synthesise and study the solid-state structures of a series of silver(I) aminoA C H T U N G T R E N N U N G areneA C H T U N G T R E N N U N G sulfonates as precursors to their bismuthA C H T U N G T R E N N U N G (III) analogues, the results of which have been reported elsewhere. [9] Herein, we describe the synthesis, characterisation and bactericidal activity against three strains of H. pylori 1 12, of which the solid state structures 10 and 12 are presented (2P-SO 3 À = 2-pyridinesulfonate). These complexes offer remarkable in-vitro ac-tivity against three standard laboratory strains of Helicobacter pylori (H. pylori) as demonstrated by their exceptionally low minimum inhibitory concentration (MIC) values of 0.049 mg mL À1 for the strains 251 and B128, which places most MIC values in the nano-molar region.…”