In silico design of supramolecules from their precursors: odd–even effects in cage-forming reactions

Jelfs, K. E., Eden, E. G. B., Culshaw, J. L., Shakespeare, S., Pyzer-Knapp, E. O., Thompson, H. P. G., Bacsa, J., Day, G. M., Adams, D. J. and Cooper, A. I. (2013) In silico design of supramolecules from their precursors: odd–even effects in cage-forming reactions. Journal of the American Chemical Society, 135(25), pp. 9307-9310. (doi: 10.1021/ja404253j) (PMID:23745577) (PMCID:PMC3697021)

Abstract

We synthesize a series of imine cage molecules where increasing the chain length of the alkanediamine precursor results in an odd–even alternation between [2 + 3] and [4 + 6] cage macrocycles. A computational procedure is developed to predict the thermodynamically preferred product and the lowest energy conformer, hence rationalizing the observed alternation and the 3D cage structures, based on knowledge of the precursors alone.

• Item Type: Articles
• Status: Published
• Refereed: Yes
• Glasgow Author(s) Enlighten ID: Adams, Dave
• Authors: Jelfs, K. E., Eden, E. G. B., Culshaw, J. L., Shakespeare, S., Pyzer-Knapp, E. O., Thompson, H. P. G., Bacsa, J., Day, G. M., Adams, D. J., and Cooper, A. I.
• College/School: College of Science and Engineering > School of Chemistry
• Journal Name: Journal of the American Chemical Society
• Publisher: American Chemical Society
• ISSN: 0002-7863
• ISSN (Online): 520-5126
• Published Online: 07 June 2013