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Title: Aplicyanins - Brominated natural marine products with superbasic character
Authors: Kostic, Marina
Divac, Vera
Alzoubi, Basam
Puchta, Ralph
Issue Date: 2016
Abstract: © 2016, Verlag der Zeitschrift fur Naturforschung. All rights reserved. By using quantum chemical methods (B3LYP/6-311+G(2df,p)//B3LYP/6-31G(d)), we investigated the structures of aplicyanin A, aplicyanin B, aplicyanin C, aplicyanin D, aplicyanin E, and aplicyanin F along with their protonated structures. The calculated gas phase proton affinities of aplicyanin A, aplicyanin C, and aplicyanin E are around -250 kcal mol-1 and therefore more than 10 kcal mol-1 higher as in typical proton sponges such as 1,8-bis(dimethylamino)naphthalene. The compounds aplicyanin B, aplicyanin D, and aplicyanin F show reduced proton affinities of approximately -240 kcal mol-1 because of the acetyl group being conjugated with the imine N=C moiety. Nucleus-independent chemical shift (NICS) calculations on the same level of theory do not show any peculiarities, and a reasonable correlation between the toxicity of aplicyanins and the gas phase proton affinity is not observed.
Type: article
DOI: 10.1515/znb-2016-0055
ISSN: 0932-0776
SCOPUS: 2-s2.0-84990055889
Appears in Collections:Faculty of Science, Kragujevac
Institute for Information Technologies, Kragujevac

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