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Upon reacting with these gases, calixarenes <jats:bold>1<\/jats:bold> encapsulate nitrosonium (NO<jats:sup>+<\/jats:sup>) cations within their cavities with the formation of stable calixarene\u2013NO<jats:sup>+<\/jats:sup> complexes <jats:bold>2<\/jats:bold>. These complexes act as encapsulated nitrosating reagents; cavity effects control their reactivity and selectivity. Complexes <jats:bold>2<\/jats:bold> were effectively used for nitrosation of secondary amides <jats:bold>5<\/jats:bold>, including chiral derivatives. Unique size\u2013shape selectivity was observed, allowing for exclusive nitrosation of less crowded <jats:italic>N<\/jats:italic>\u2010Me amides <jats:bold>5\u2009a<\/jats:bold>\u2013<jats:bold>e<\/jats:bold> (up to 95\u2009% yields). Bulkier <jats:italic>N<\/jats:italic>\u2010Alk (Alk&gt;Me) substrates <jats:bold>5<\/jats:bold> did not react due to the hindered approach to the encapsulated NO<jats:sup>+<\/jats:sup> reagents. Robust, silica gel based calixarene material <jats:bold>3<\/jats:bold> was prepared, which reversibly traps NO<jats:sub>2<\/jats:sub>\/N<jats:sub>2<\/jats:sub>O<jats:sub>4<\/jats:sub> with the formation of NO<jats:sup>+<\/jats:sup>\u2010storing silica gel <jats:bold>4<\/jats:bold>. With material <jats:bold>4<\/jats:bold>, similar size\u2013shape selectivity was observed for nitrosation. The <jats:italic>N<\/jats:italic>\u2010Me\u2013<jats:italic>N<\/jats:italic>\u2010nitroso derivatives <jats:bold>6\u2009d<\/jats:bold>,<jats:bold>e<\/jats:bold> were obtained with \u223c30\u2009% yields, while bulkier amides were nitrosated with much lower yields (&lt;8\u2009%). Enantiomerically pure encapsulating reagent <jats:bold>2\u2009d<\/jats:bold> was tested for nitrosation of racemic amide <jats:bold>5\u2009t<\/jats:bold>, showing modest but reproducible stereoselectivity and \u223c15\u2009% <jats:italic>ee<\/jats:italic>. Given high affinity to NO<jats:sup>+<\/jats:sup> species, which can be generated by a number of NO<jats:sub><jats:italic>X<\/jats:italic><\/jats:sub> gases, these supramolecular reagents and materials may be useful for NO<jats:sub><jats:italic>X<\/jats:italic><\/jats:sub> entrapment and separation in the environment and biomedical areas.<\/jats:p>","DOI":"10.1002\/chem.200400939","type":"journal-article","created":{"date-parts":[[2005,1,26]],"date-time":"2005-01-26T11:49:38Z","timestamp":1106740178000},"page":"1924-1932","source":"Crossref","is-referenced-by-count":28,"title":["Towards Supramolecular Fixation of NO<sub><i>X<\/i><\/sub> Gases: Encapsulated Reagents for Nitrosation"],"prefix":"10.1002","volume":"11","author":[{"given":"Yanlong","family":"Kang","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Grigory V.","family":"Zyryanov","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Dmitry M.","family":"Rudkevich","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2005,2,25]]},"reference":[{"key":"e_1_2_6_1_2","unstructured":"U. 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