Journal article
The influence of cation upon the supramolecular aggregation patterns of dithiocarbamate anions functionalised with hydrogen bonding capacity - The prevalence of charge-assisted O-H⋯S interactions
CrystEngComm, Vol.10(11), pp.1626-1637
2008
Abstract
A range of supramolecular architectures is found in the title dithiocarbamate salts, each with hydrogen bonding functionality in the form of aÏ„ least one hydroxyl group. A common feature in the crystal packing is the prevalence of charge-assisted O-H⋯S hydrogen bonding. In [NH 4][S2CN(CH2CH2OH)2] (1), a 3-D network is found mediated by cooperative O-H⋯S, N-H⋯O and N-H⋯S hydrogen bonding. Reducing the hydrogen bonding functionality by replacing the ammonium cation in (1) by the 4-aza-1-azoniabicyclo(2.2.2)octanium cation to give [DABCO-H][S2CN(CH2CH2OH) 2] (2), results in a 2-D array. Further reduction of the hydrogen bonding functionality, this time by substituting a CH2CH 2OH with an alkyl group to give [DABCO-H][S2CN(CH 2CH2OH)CH3] (3) and [DABCO-H][S 2CN(CH2CH2OH)CH2CH3] (4) allows for the formation of 1-D supramolecular chains. The introduction of alkali metal cations rather than protic cations removes the possibility of the hydroxyl-O participating in hydrogen bonding interactions as these now coordinate the alkali metal. In the sodium trihydrate, Na[S 2CN(CH2CH2OH)2].3H 2O (5), O-H⋯O hydrogen bonds are found along with charge-assisted O-H⋯S contacts so that a 3-D network results. Substituting a CH2CH2OH group with a n-propyl group gives Na[S2CN(CH2CH2OH)CH2CH 2CH3].2H2O (6) and yields a 2-D array. For the anhydrous K[S2CN(CH2CH2OH)2] (7) and Cs[S2CN(CH2CH2OH)2] (8) salts, the crystal packing is dominated by charge-assisted O-H⋯S hydrogen bonding giving 3-D network structures. The systematic analysis of the crystal packing patterns of these salts reveals the importance of charge-assisted O-H⋯S hydrogen bonding in stabilising these crystal structures. © The Royal Society of Chemistry.
Details
- Title
- The influence of cation upon the supramolecular aggregation patterns of dithiocarbamate anions functionalised with hydrogen bonding capacity - The prevalence of charge-assisted O-H⋯S interactions
- Authors
- R A Howie (Author) - University of Aberdeen, United KingdomG M De Lima (Author) - Universidade Federal de Minas Gerais, BrazilD C Menezes (Author) - Universidade Federal de Minas Gerais, BrazilJ L Wardell (Author) - Instituto de Tecnologia em Farmacos-FarManguinhos, BrazilS M S V Wardell (Author) - Instituto de Tecnologia em Farmacos-FarManguinhos, BrazilDavid James Young (Author) - Griffith UniversityE R T Tiekink (Author) - University of Texas, United States
- Publication details
- CrystEngComm, Vol.10(11), pp.1626-1637
- Publisher
- Royal Society of Chemistry (R S C) Publications
- Date published
- 2008
- DOI
- 10.1039/b809730e
- ISSN
- 1466-8033
- Organisation Unit
- University of the Sunshine Coast, Queensland
- Language
- English
- Record Identifier
- 99449110502621
- Output Type
- Journal article
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- Web Of Science research areas
- Chemistry, Multidisciplinary
- Crystallography
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