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Proton behavior within the hydrogen bond (HB) networks of five molecular complexes of the proton sponge DMAN and different organic acids is investigated by single crystal neutron diffraction. The complexes form with either 2:1 (acid:DMAN) or 1:1 stoichiometric ratios and contain common structural motifs. All show proton transfer from an acid to DMAN forming a DMANH+ moiety and hydrogen bonded acid dimers; complexes with halobenzoic acids have acid molecules linked by short, strong, charge-assisted HBs, while all complexes contain a short, strong, intramolecular N-H N HB in DMANH+. The hydrogen atom behavior within the short, strong HBs, accurately described from the neutron data, is rationalized in terms of weak interactions in the local crystal environment, with the position of the proton within both sets of short, strong HBs affected by a combination of the weak interactions in the vicinity of the HBs. A correlation is also found between the thermal motion of the bound proton in the N H N HB of DMANH+ and nearby oxygen atoms when they are sufficiently close to one another. This work shows that all interactions in the local environment combine to determine the behavior of protons within short, strong HBs and that by taking these interactions into account further control over the crystal structure and properties may be achievable

The Effect of Local Crystalline Environment on Hydrogen Atom Behavior in Molecular Complexes of a Proton Sponge