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Thus, <jats:bold>A<\/jats:bold> reacts with oxygen gas to give the <jats:italic>syn<\/jats:italic>\u2010bis(urea) <jats:bold>1<\/jats:bold> and with sulfur to yield the <jats:italic>anti<\/jats:italic>\u2010bis(thiourea) <jats:bold>2<\/jats:bold>. The reaction of <jats:bold>A<\/jats:bold> with triflic acid furnishes the bis(imidazolium) triflate <jats:bold>3<\/jats:bold>, which gives the monoprotonated imidazolium salt <jats:bold>4<\/jats:bold> upon treatment with sodium tetraphenylborate in water. Theoretical calculations (DFT) predict the diprotonated species to be energetically disfavoured, thus demonstrating the importance of hydrogen\u2010bonding interactions. Treatment of compound <jats:bold>3<\/jats:bold> with silver oxide affords the di\u2010 and monoprotonated cationic salts <jats:bold>5a<\/jats:bold> and <jats:bold>5b<\/jats:bold> in THF and dichloromethane, respectively. The molecular structures of compounds <jats:bold>1<\/jats:bold>, <jats:bold>2<\/jats:bold>, <jats:bold>3<\/jats:bold>, <jats:bold>4<\/jats:bold>, <jats:bold>5a<\/jats:bold> and <jats:bold>5b<\/jats:bold> have been established by X\u2010ray diffraction. (\u00a9 Wiley\u2010VCH Verlag GmbH &amp; Co. 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