Unusual behavior of cytosine amino group signal in <sup>1</sup>H NMR spectra in DMSO depending on its concentration

Andriy L. Potyahaylo; Svitlana P. Samijlenko; Andriy V. Stepanyugin; Dmytro M. Hovorun

doi:10.1117/12.569624

20 July 2004 Unusual behavior of cytosine amino group signal in ¹H NMR spectra in DMSO depending on its concentration

Andriy L. Potyahaylo, Svitlana P. Samijlenko, Andriy V. Stepanyugin, Dmytro M. Hovorun

Proceedings Volume 5507, XVI International Conference on Spectroscopy of Molecules and Crystals; (2004) https://doi.org/10.1117/12.569624
Event: XVI International Conference on Spectroscopy of Molecules and Crystals, 2003, Sevastopol, Ukraine

Abstract

By ¹H NMR spectroscopy it was established that under increase ofcytosine concentration in anhydrous DMSO-d₆ from 5 up to 35 mM the doublet signal of its amino group becomes gradually transformed into singlet one. This observation is interpreted as a result of lowering of the barrier of amino group turn due to central symmetrical self-association of the base through two equivalent intermolecular H-bonds N1H...O=C2, which is likely to weaken pπ-conjugation of lone electron pair ofthe amino nitrogen atom with the ring π-electron system. The cytosine N1-methylsubstitution was shown to impact amino group in the similar way as self-association.

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Andriy L. Potyahaylo, Svitlana P. Samijlenko, Andriy V. Stepanyugin, and Dmytro M. Hovorun "Unusual behavior of cytosine amino group signal in ¹H NMR spectra in DMSO depending on its concentration", Proc. SPIE 5507, XVI International Conference on Spectroscopy of Molecules and Crystals, (20 July 2004); https://doi.org/10.1117/12.569624

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