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Structural diversity in imidazolidinone organocatalysts: a synchrotron and computational study

Burley, Jonathan C., Gilmour, Ryan, Prior, Timothy J. and Day, Graeme M. (2008) Structural diversity in imidazolidinone organocatalysts: a synchrotron and computational study Acta Crystallographica Section C Crystal Structure Communications, 64, (1), o10-o14. (doi:10.1107/S0108270107051396).

Record type: Article


(S)-1-(Methylaminocarbonyl)-3-phenylpropanaminium chloride (S2·HCl), C10H15N2O+·Cl-, crystallizes in the orthorhombic space group P212121 with a single formula unit per asymmetric unit. (5R/S)-5-Benzyl-2,2,3-trimethyl-4-oxoimidazolidin-1-ium chloride (R3 and S3), C13H19N2O+·Cl-, crystallize in the same space group as S2·HCl but contain three symmetry-independent formula units. (R/S)-5-Benzyl-2,2,3-trimethyl-4-oxoimidazolidin-1-ium chloride monohydrate (R4 and S4), C13H19N2O+·Cl-·H2O, crystallize in the space group P21 with a single formula unit per asymmetric unit. Calculations at the B3LYP/6-31G(d,p) and B3LYP/6-311G(d,p) levels of the conformational energies of the cation in R3, S3, R4 and S4 indicate that the ideal gas-phase global energy minimum conformation is not observed in the solid state. Rather, the effects of hydrogen-bonding and van der Waals interactions in the crystal structure cause the molecules to adopt higher-energy conformations, which correspond to local minima in the molecular potential energy surface.

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Published date: January 2008
Organisations: Organic Chemistry: Synthesis, Catalysis and Flow, Computational Systems Chemistry


Local EPrints ID: 343442
ISSN: 0108-2701
PURE UUID: 9577395b-1147-466c-bae0-90851cbe97ca
ORCID for Graeme M. Day: ORCID iD

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Date deposited: 08 Oct 2012 11:14
Last modified: 18 Jul 2017 05:22

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Author: Jonathan C. Burley
Author: Ryan Gilmour
Author: Timothy J. Prior
Author: Graeme M. Day ORCID iD

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