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 journalArticle

1 Citation (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

Fingerprint

Naphthalene
naphthalene
Protons
Hydrogen bonds
Substitution reactions
Tuning
tuning
substitutes
hydrogen bonds
acids
Acids
protons
Stoichiometry
stoichiometry
Proton transfer
Benzoic Acid
Benzoic acid
benzoic acid
Crystal structure
solid state

Keywords

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

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Tuning charge-assisted and weak hydrogen bonds in molecular complexes of the proton sponge DMAN by acid co-former substitution. / Saunders, Lucy Katherine; Nowell, Harriott; Spencer, Helen C. E.; Hatcher, Lauren E.; Shepherd, Helena; Thomas, Lynne; Jones, Charlotte; Teat, Simon J; Raithby, Paul; Wilson, Chick C.

In: CrystEngComm, Vol. 20, No. 22, 14.06.2018, p. 3074-3083.

Research output: Contribution to journalArticle

Saunders, LK, Nowell, H, Spencer, HCE, Hatcher, LE, Shepherd, H, Thomas, L, Jones, C, Teat, SJ, Raithby, P & Wilson, CC 2018, 'Tuning charge-assisted and weak hydrogen bonds in molecular complexes of the proton sponge DMAN by acid co-former substitution', CrystEngComm, vol. 20, no. 22, pp. 3074-3083. https://doi.org/10.1039/C8CE00443A
Saunders, Lucy Katherine ; Nowell, Harriott ; Spencer, Helen C. E. ; Hatcher, Lauren E. ; Shepherd, Helena ; Thomas, Lynne ; Jones, Charlotte ; Teat, Simon J ; Raithby, Paul ; Wilson, Chick C. / Tuning charge-assisted and weak hydrogen bonds in molecular complexes of the proton sponge DMAN by acid co-former substitution. In: CrystEngComm. 2018 ; Vol. 20, No. 22. pp. 3074-3083.
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