Tuning charge-assisted and weak hydrogen bonds in molecular complexes of the proton sponge DMAN by acid co-former substitutionElectronic supplementary information (ESI) available: Crystal structure refinement details; selected molecular geometry tables, selected hydrogen bond tables, fingerprint plots/Hirshfeld surfaces. CCDC 18316381831646. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c8ce00443a

Tuning charge-assisted and weak hydrogen bonds in molecular complexes of the proton sponge DMAN... 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 [NHN]+ 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. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png CrystEngComm Royal Society of Chemistry

Tuning charge-assisted and weak hydrogen bonds in molecular complexes of the proton sponge DMAN by acid co-former substitutionElectronic supplementary information (ESI) available: Crystal structure refinement details; selected molecular geometry tables, selected hydrogen bond tables, fingerprint plots/Hirshfeld surfaces. CCDC 18316381831646. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c8ce00443a

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Publisher
Royal Society of Chemistry
Copyright
This journal is © The Royal Society of Chemistry
ISSN
1466-8033
D.O.I.
10.1039/c8ce00443a
Publisher site
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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 [NHN]+ 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.

Journal

CrystEngCommRoyal Society of Chemistry

Published: May 17, 2018

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