Protonation-triggered conformational modulation of an N,N?-dialkylbispidine: first observation of the elusive boat–boat conformer
Protonation-triggered conformational modulation of an N,N?-dialkylbispidine: first observation of the elusive boat–boat conformer
Modulation of the solution conformations of N,N?-bis(benzhydryl)bispidine has been achieved by protonation. Conformers have been characterized by NMR spectroscopy using nuclear Overhauser effects and residual dipolar couplings. In contrast to the preference for the chair–chair conformation for the free base and the monoprotonated species, the diprotonated bispidine is revealed to exist as a mixture of chair–boat and boat–boat conformers. While boat–boat conformers of bispidines have previously not been detected, they are here observed to constitute up to 70% of the bispidine population.
6292-6299
Norrehed, Sara
f3df8490-6239-405c-90b9-b006449d03bb
Erdélyi, Máté
d5a578ec-e046-4b86-a546-a5ecb1488398
Light, Mark E.
cf57314e-6856-491b-a8d2-2dffc452e161
Gogoll, Adolf
1769b3c3-6b75-496a-ac4b-89041c2d5126
7 October 2013
Norrehed, Sara
f3df8490-6239-405c-90b9-b006449d03bb
Erdélyi, Máté
d5a578ec-e046-4b86-a546-a5ecb1488398
Light, Mark E.
cf57314e-6856-491b-a8d2-2dffc452e161
Gogoll, Adolf
1769b3c3-6b75-496a-ac4b-89041c2d5126
Norrehed, Sara, Erdélyi, Máté, Light, Mark E. and Gogoll, Adolf
(2013)
Protonation-triggered conformational modulation of an N,N?-dialkylbispidine: first observation of the elusive boat–boat conformer.
Organic & Biomolecular Chemistry, 11 (37), .
(doi:10.1039/c3ob41122b).
Abstract
Modulation of the solution conformations of N,N?-bis(benzhydryl)bispidine has been achieved by protonation. Conformers have been characterized by NMR spectroscopy using nuclear Overhauser effects and residual dipolar couplings. In contrast to the preference for the chair–chair conformation for the free base and the monoprotonated species, the diprotonated bispidine is revealed to exist as a mixture of chair–boat and boat–boat conformers. While boat–boat conformers of bispidines have previously not been detected, they are here observed to constitute up to 70% of the bispidine population.
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Accepted/In Press date: 24 July 2013
e-pub ahead of print date: 25 July 2013
Published date: 7 October 2013
Identifiers
Local EPrints ID: 385742
URI: http://eprints.soton.ac.uk/id/eprint/385742
ISSN: 1477-0520
PURE UUID: 80b80b60-2466-40d3-8f0a-bda7331ac2f1
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Date deposited: 21 Jan 2016 15:22
Last modified: 15 Mar 2024 03:01
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Contributors
Author:
Sara Norrehed
Author:
Máté Erdélyi
Author:
Adolf Gogoll
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