In silico design of supramolecules from their precursors: Odd–even effects in cage-forming reactions
In silico design of supramolecules from their precursors: Odd–even effects in cage-forming reactions
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.
9307-9310
Jelfs, K. E.
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Eden, E. G. B.
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Culshaw, J. L.
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Shakespeare, S.
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Pyzer-Knapp, E. O.
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Thompson, H. P. G.
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Bacsa, J.
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Day, Graeme M.
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Adams, D. J.
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Cooper, A. I.
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7 June 2013
Jelfs, K. E.
ccf9118d-bf0e-4401-a980-dddfe0c1dfc9
Eden, E. G. B.
63a16afb-c505-4619-820a-223964e39250
Culshaw, J. L.
978fddc6-a111-4373-8e49-3fc655294ec5
Shakespeare, S.
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Pyzer-Knapp, E. O.
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Thompson, H. P. G.
775ef184-3196-4b84-926a-d85b787eef4c
Bacsa, J.
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Day, Graeme M.
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Adams, D. J.
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Cooper, A. I.
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Jelfs, K. E., Eden, E. G. B., Culshaw, J. L., Shakespeare, S., Pyzer-Knapp, E. O., Thompson, H. P. G., Bacsa, J., Day, Graeme 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), .
(doi:10.1021/ja404253j).
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.
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Published date: 7 June 2013
Organisations:
Organic Chemistry: SCF
Identifiers
Local EPrints ID: 354127
URI: http://eprints.soton.ac.uk/id/eprint/354127
ISSN: 0002-7863
PURE UUID: f02b4f44-86f2-4990-8d83-3ef709b6f769
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Date deposited: 01 Jul 2013 15:50
Last modified: 15 Mar 2024 03:44
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Contributors
Author:
K. E. Jelfs
Author:
E. G. B. Eden
Author:
J. L. Culshaw
Author:
S. Shakespeare
Author:
E. O. Pyzer-Knapp
Author:
H. P. G. Thompson
Author:
J. Bacsa
Author:
D. J. Adams
Author:
A. I. Cooper
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