Abstract
The transannular N...C=O interaction in several medium-sized heterocycles has been investigated by force-field methods. Conformational searching has been performed at the molecular mechanics level using different methods and the conformers so generated have been reoptimized at RHF/6-31G(d). For selected conformers, N...C distances are reported, together with transannular bond orders and atomic charges. Good agreement with available X-ray crystallographic data is obtained for the transannular bond distance in cryptopine. Changes in the partial atomic charges derived from the electrostatic potential provide good support for the donor-acceptor model of transannular interactions. Partial charges derived with other methods do not give satisfactory results. Some force fields do not reproduce the transannular interaction very well. This is demonstrated and rationalized, and modifications are suggested and tested for these force fields with good results when comparing diagnostic geometric features with X-ray data.
Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
