Othersen O, Beierlein F, Lanig H, Clark T (2003)
Publication Status: Published
Publication Type: Journal article
Publication year: 2003
Publisher: American Chemical Society
Book Volume: 107
Pages Range: 13743-13749
Journal Issue: 49
DOI: 10.1021/jp0364506
Density functional theory (DFT) has been used to investigate the conformations and tautomeric forms of neutral tetracycline in aqueous solution. The results suggest that the extended conformation is 3-3.5 kcal mol(-1) more stable than the twisted one for equivalent tautomers and that as many as six different tautomeric forms lie within 10 kcal mol(-1) of the most stable one. The energetic preference for the extended conformation is a solvent effect. Calculated infrared, NMR, and UV/vis spectra are used to suggest ways of differentiating between tautomers. and conformations experimentally. It is shown that the (13)C chemical shifts of C4a, C5, and C6 can be used to distinguish between the twisted and extended conformations.
APA:
Othersen, O., Beierlein, F., Lanig, H., & Clark, T. (2003). Conformations and tautomers of tetracycline. Journal of Physical Chemistry B, 107(49), 13743-13749. https://dx.doi.org/10.1021/jp0364506
MLA:
Othersen, Olaf, et al. "Conformations and tautomers of tetracycline." Journal of Physical Chemistry B 107.49 (2003): 13743-13749.
BibTeX: Download