<?xml version="1.0" encoding="UTF-8" standalone="yes"?><oembed><version><![CDATA[1.0]]></version><provider_name><![CDATA[amphoteros]]></provider_name><provider_url><![CDATA[http://amphoteros.com]]></provider_url><author_name><![CDATA[ayudin2013]]></author_name><author_url><![CDATA[https://amphoteros.com/author/ayudin2013/]]></author_url><title><![CDATA[Reversible covalent interactions]]></title><type><![CDATA[link]]></type><html><![CDATA[<p>Happy New Year, everyone! I am back.</p>
<p>There are many types of reversible covalent interactions but the one I am most curious about these days is the one between two nitrogens. I learned about it from Professor Jim Wuest (<a href="http://www.wuestgroup.com" rel="nofollow">http://www.wuestgroup.com</a>) while visiting Université de Montréal just before Christmas. Jim and his lab leverage the reversible coupling between nitroso compounds to make materials of controlled porosity. Being a small molecule guy, I am intrigued by the pair of reactions I saw in his nice <em>Chemical Reviews</em> account (<a href="http://pubs.acs.org/doi/abs/10.1021/cr500520s" rel="nofollow">http://pubs.acs.org/doi/abs/10.1021/cr500520s</a>). Why is it that a 6-membered ring is not formed in the naphthalene case? There are a couple of lessons about aromaticity and strain here, among other things. This fascinating type of N=N bonding also takes me back to some of my earlier claims about the rarity of heterocycle construction using heteroatom-heteroatom bond formation. Here it is on display. However, these heterocycles are metastable.</p>
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