Structural diversity in imidazolidinone organocatalysts: A synchrotron and computational study

Prior, Timothy; Burley, Jonathan C.; Gilmour, Ryan; Prior, Timothy J.; Day, Graeme M.

Abstract

(5)-1-(Methylaminocarbonyl)-3-phenylpropanaminium chloride (52·HCl), C 10 H 15 N 2 O + ·Cl - , crystallizes in the orthorhombic space group P2 1 2 1 2 1 with a single formula unit per asymmetric unit. (5R/S)-5-Benzyl-2,2,3-trimethyl-4-oxoimidazolidin-1-ium chloride (R3 and S3), C 13 H 19 N 2 O + ·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), C 13 H 19 N 2 O + -Cl - ·H 2 O, crystallize in the space group P2 1 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. © 2008 International Union of Crystallography.

Citation

Burley, J. C., Gilmour, R., Prior, T. J., & Day, G. M. (2008). Structural diversity in imidazolidinone organocatalysts: A synchrotron and computational study. Acta Crystallographica Section C: Crystal Structure Communications, 64(1), O10-O14. https://doi.org/10.1107/S0108270107051396

• Journal Article Type: Article
• Acceptance Date: Oct 17, 2007
• Online Publication Date: Dec 14, 2007
• Publication Date: 2008-01
• Journal: ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS
• Print ISSN: 0108-2701
• Electronic ISSN: 0108-2701
• Publisher: International Union of Crystallography
• Peer Reviewed: Peer Reviewed
• Volume: 64
• Issue: 1
• Pages: O10-O14
• DOI: https://doi.org/10.1107/S0108270107051396
• Keywords: General Biochemistry, Genetics and Molecular Biology; General Medicine
• Public URL: https://hull-repository.worktribe.com/output/396237
• Publisher URL: http://scripts.iucr.org/cgi-bin/paper?S0108270107051396
• Additional Information: Journal: Acta Crystallographica Section C: Crystal Structure Communications; Content type: organic compounds; Peer reviewed: Yes; Review process: Single blind; Received: 17 August 2007; Accepted: 17 October 2007; Published online: 14 December 2007; Supplementary materials: This article has supplementary materials; Copyright: © 2008 International Union of Crystallography