A hydrogen bond is formed between hydrogen attached to highly electronegative atoms (nitrogen, oxygen, and fluorine) which are small in size too and the non-bonding pair of electrons of another such atom that may be present in the same molecule or in another molecule but is not directly linked to it with a covalent bond. But when we talk about chlorine, it doesn't form hydrogen bond due to its large size. But what happens in the case of carbon more precisely 'carbenes'? It's small in size, has a lone pair of electrons and is somehow more electronegative too. Does it help form H-bond like N, O, and F do?

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    $\begingroup$ Wait... You're asking whether a hydrogen bond was found with C lone pair? I think it may be possible, but there's a lot of things you mention that aren't exactly true. Your thinking about these bonds is somewhat outdated - virtually any atom may be acceptor or donor, it's just that bond with donor should be significantly polarised or h-bond with acceptor will have negligible energy. $\endgroup$ – Mithoron Sep 14 '19 at 20:47
  • $\begingroup$ I'm waiting for an organic chemist to comment or answer this question, but in the meantime my opinion is that a carbene is too reactive to do anything as subtle as form a stable H-bond. But perhaps that is not relevant to the question. It is perhaps more of a hypothetical question. $\endgroup$ – Buck Thorn Sep 15 '19 at 8:09
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    $\begingroup$ @BuckThorn There's a lot of stable carbenes, also radicals, cation/anion radicals etc. You name it, it can be stabilised. In particular NHC carbenes are often used as ligands, but their high basicity may be a problem for non-transient hydrogen bond. $\endgroup$ – Mithoron Sep 15 '19 at 17:04

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