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Tuning charge-assisted and weak hydrogen bonds in molecular complexes of the proton sponge DMAN by acid co-former substitution

DOI: 10.1039/C8CE00443A DOI Help

Authors: Lucy K. Saunders (Diamond Light Source) , Harriott Nowell (Diamond Light Source) , Helen C. E. Spencer (University of Bath) , Lauren E. Hatcher (University of Bath) , Helena J. Shepherd (University of Bath; University of Kent) , Lynne H. Thomas (University of Bath) , Charlotte L. Jones (University of Bath) , Simon J. Teat (Advanced Light Source) , Paul R. Raithby (University of Bath; Research Complex at Harwell) , Chick C. Wilson (University of Bath)
Co-authored by industrial partner: No

Type: Journal Paper
Journal: Crystengcomm , VOL 112

State: Published (Approved)
Published: May 2018
Diamond Proposal Number(s): 8803

Open Access Open Access

Abstract: Nine new molecular complexes of the proton sponge 1,8-bis(dimethylamino)naphthalene (DMAN) with substituted benzoic acid co-formers have been engineered with varying component stoichiometries (1[thin space (1/6-em)]:[thin space (1/6-em)]1, 1[thin space (1/6-em)]:[thin space (1/6-em)]2 or 1[thin space (1/6-em)]:[thin space (1/6-em)]3). These complexes are all ionic in nature, following proton transfer between the acid co-former and DMAN; the extracted proton is held by DMAN in all instances in an intramolecular [N–H⋯N]+ hydrogen bond. A number of structural features are common to all complexes and are found to be tunable in a predictable way using systematic acid co-former substitution. These features include charge-assisted hydrogen bonds formed between acid co-formers in hydrogen bonding motifs consistent with complex stoichiometry, and weak hydrogen bonds which facilitate the crystal packing of DMAN and acid co-former components into a regular motif. Possible crystal structure tuning by co-former substitution can aid the rational design of such materials, offering the potential to target solid-state properties that may be influenced by these interactions

Subject Areas: Chemistry


Instruments: I19-Small Molecule Single Crystal Diffraction

Other Facilities: Advanced Light Source

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C8CE00443A.pdf