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

Lucy Katherine Saunders, Harriott Nowell, Helen C. E. Spencer, Lauren E. Hatcher, Helena Shepherd, Lynne Thomas, Charlotte Jones, Simon J Teat, Paul Raithby, Chick C. Wilson

Research output: Contribution to journalArticlepeer-review

3 Citations (Scopus)

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 (1:1, 1:2 or 1:3). 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.
Original languageEnglish
Pages (from-to)3074-3083
Number of pages10
JournalCrystEngComm
Volume20
Issue number22
Early online date9 May 2018
DOIs
Publication statusPublished - 14 Jun 2018

Keywords

  • Hydrogen bonding
  • X-ray crystallography
  • Charge-assisted

ASJC Scopus subject areas

  • Chemistry(all)

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