Can a C-H···O interaction be a determinant of conformation?

DOI: 10.1021/ja301318a

Authors: Christopher R. Jones (University of Oxford) , Pranjal K. Baruah (University of Oxford) , Amber Thompson (University of Oxford) , Steve Scheiner (Utah State University) , Martin D. Smith (University of Oxford)
Co-authored by industrial partner: No

Type: Journal Paper
Journal: Journal Of The American Chemical Society , VOL 134 (29) , PAGES 12064 - 12071

State: Published (Approved)
Published: July 2012
Diamond Proposal Number(s): 1858

Abstract: Whether nonconventional hydrogen bonds, such as the C–H···O interaction, are a consequence or a determinant of conformation is a long-running and unresolved issue. Here we outline a solid-state and quantum mechanical study designed to investigate whether a C–H···O interaction can override the significant trans-planar conformational preferences of ?-fluoroamide substituents. A profound change in dihedral angle from trans-planar(OCCF) to cis-planar(OCCF) observed on introducing an acceptor group for a C–H···O hydrogen bond is consistent with this interaction functioning as a determinant of conformation in certain systems. This testifies to the potential influence of the C–H···O hydrogen bond and is consistent with the assignment of this interaction as a contributor to overall conformation in both model and natural systems.

Subject Areas: Chemistry


Instruments: I19-Small Molecule Single Crystal Diffraction

Added On: 06/02/2013 09:50

Discipline Tags:

Chemistry Organic Chemistry

Technical Tags:

Diffraction Single Crystal X-ray Diffraction (SXRD)