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It is known that very strong hydrogen bonds can occur in charged systems, such as $\ce{[F-}\ce{-H+-F-]}$, while hydrogen bonds in neutral systems are much weaker in comparison.

What is the strongest known hydrogen bond within the following specifications?

  • both donor and acceptor monomers are neutral, and remain neutral upon association (no ionic bridges);
  • heterodimers are allowed (e.g. hydrogen fluoride and ammonia);
  • must be a single-site hydrogen bond - excluding dimers stabilized by multiple hydrogen bonds such as nucleobase pairs.
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    $\begingroup$ Well, you should change "possible" to known, otherwise it's speculation. $\endgroup$ – Mithoron Feb 7 '18 at 0:11
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    $\begingroup$ Also this: chemistry.stackexchange.com/questions/47346/… is highly relevant here. $\endgroup$ – Mithoron Feb 7 '18 at 0:12
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    $\begingroup$ This sounds like it could be a good target for design golf... $\endgroup$ – Nicolau Saker Neto Feb 7 '18 at 0:54
  • $\begingroup$ It probably is $\ce{HF}$ and $\ce{NH3}$. It's hard to get a better donor and acceptor pair than that. It's always possible one could find some very obscure system where a hydrogen becomes quite positively charged, but for small molecules I'd be surprised if something beats $\ce{HF}$ and $\ce{NH3}$. $\endgroup$ – jheindel Feb 9 '18 at 7:04

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