Aplicyanins - Brominated natural marine products with superbasic character
Alzoubi B, Puchta R (2016)
Publication Type: Journal article
Publication year: 2016
Journal
Book Volume: 71
Pages Range: 883-889
Journal Issue: 8
Abstract
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.
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APA:
Alzoubi, B., & Puchta, R. (2016). Aplicyanins - Brominated natural marine products with superbasic character. Zeitschrift für Naturforschung - Section B Journal of Chemical Sciences, 71(8), 883-889. https://doi.org/10.1515/znb-2016-0055
MLA:
Alzoubi, Basam, and Ralph Puchta. "Aplicyanins - Brominated natural marine products with superbasic character." Zeitschrift für Naturforschung - Section B Journal of Chemical Sciences 71.8 (2016): 883-889.
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