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).

Download

Full text not available from this repository.

Description/Abstract

(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.

Item Type: Article
ISSNs: 0108-2701 (print)
Subjects: Q Science > QD Chemistry
Divisions: Faculty of Natural and Environmental Sciences > Chemistry > Computational Systems Chemistry
Faculty of Natural and Environmental Sciences > Chemistry > Molecular Assembly, Function & Structure
ePrint ID: 343442
Date Deposited: 08 Oct 2012 11:14
Last Modified: 27 Mar 2014 20:25
URI: http://eprints.soton.ac.uk/id/eprint/343442

Actions (login required)

View Item View Item