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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.
diogom
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    Well, you should change "possible" to known, otherwise it's speculation. – Mithoron Feb 07 '18 at 00:11
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    Also this: https://chemistry.stackexchange.com/questions/47346/do-symmetric-hydrogen-bonds-in-neutral-molecules-exist is highly relevant here. – Mithoron Feb 07 '18 at 00:12
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    This sounds like it could be a good target for design golf... – Nicolau Saker Neto Feb 07 '18 at 00:54
  • 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 $\ce{NH3}$. – jheindel Feb 09 '18 at 07:04

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