Jump to ContentJump to Main Navigation
Show Summary Details
More options …

Zeitschrift für Physikalische Chemie

International journal of research in physical chemistry and chemical physics

Editor-in-Chief: Rademann, Klaus

12 Issues per year

IMPACT FACTOR 2017: 1.144
5-year IMPACT FACTOR: 1.144

CiteScore 2017: 1.08

SCImago Journal Rank (SJR) 2017: 0.495
Source Normalized Impact per Paper (SNIP) 2017: 0.495

See all formats and pricing
More options …
Volume 227, Issue 6-7


NMR and FT-IR Studies on the Association of Derivatives of Thymidine, Adenosine, and 6-N-Methyl-Adenosine in Aprotic Solvents

Benjamin Koeppe / Erik T. J. Nibbering / Peter M. Tolstoy
  • St. Petersburg State University, V. A. Fock Institute of Physics, St. Petersburg, Russische Föderation
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
Published Online: 2013-06-03 | DOI: https://doi.org/10.1524/zpch.2013.0388


Associates of 3',5'-O-TBDMS protected derivatives of the 2'-deoxy forms of the nucleosides adenosine, 6-N-methyl-adenosine and thymidine (henceforward simply addressed by their parents' names) and further model systems in dichloromethane and Freon (CDClF2/CDF3) solutions are studied at low temperatures by 1H NMR and FT-IR spectroscopy. N⋯N distances in hydrogen bonds are estimated from chemical shifts of protons in hydrogen bonds employing geometric and spectroscopic hydrogen bond correlations. These distances are in turn employed to derive N–H stretching frequencies from IR spectroscopic hydrogen bond correlations which may be compared to corresponding experimental results. Three isomeric hydrogen bonded dimers of thymidine are characterized in Freon solution at 120 K. Binary associates of thymidine and a series of pyridines are studied; estimated N⋯N distances in the range of 3.08 to 2.85 Å are qualitatively correlated to shifts of N–H stretching bands where in all cases considerable contributions are found in the spectral region below 3000 cm-1. For adenosine, three isomeric binary associates with 4-nitrophenol are found allowing for an assessment of site-specific acceptor capabilities. In associates of thymidine and adenosine, Watson-Crick and Hoogsteen type 1:1 associates (estimated N⋯N distances of 2.85 and 2.90 Å) as well as 2:1 associates bearing only marginally longer H-bonds could be characterized. Two 1:1 associates between thymidine and 6-N-methyl-adenosine are described that are exclusively bonded via N–H⋯N bridges of about 2.97 and 3.08 Å for Watson-Crick and Hoogsteen sites, respectively, which leads to the conclusion that cooperative effects among coupled N–H⋯O and N–H⋯N hydrogen bonds in A-T base pairs are significant as formation of the N–H⋯O bond induces a contraction of around 0.15 Å in the neighboring N–H⋯N bond.

Keywords: Hydrogen Bonds; DNA Base Pairing; NMR Spectroscopy; IR Spectroscopy; Hydrogen Bond Correlations

About the article

* Correspondence address: Max Born Institut für Nichtlineare Optik und Kurzzeitspektroskopie, Max-Born-Str. 2a, 12489 Berlin, Deutschland,

Published Online: 2013-06-03

Published in Print: 2013-06-01

Citation Information: Zeitschrift für Physikalische Chemie, Volume 227, Issue 6-7, Pages 723–749, ISSN (Online) 2196-7156, ISSN (Print) 0942-9352, DOI: https://doi.org/10.1524/zpch.2013.0388.

Export Citation

© by Oldenbourg Wissenschaftsverlag, München, Germany.Get Permission

Citing Articles

Here you can find all Crossref-listed publications in which this article is cited. If you would like to receive automatic email messages as soon as this article is cited in other publications, simply activate the “Citation Alert” on the top of this page.

Brian L. Van Hoozen and Poul B. Petersen
The Journal of Chemical Physics, 2018, Volume 148, Number 13, Page 134309
B. Koeppe, S. A. Pylaeva, C. Allolio, D. Sebastiani, E. T. J. Nibbering, G. S. Denisov, H.-H. Limbach, and P. M. Tolstoy
Phys. Chem. Chem. Phys., 2017, Volume 19, Number 2, Page 1010
Jordi Poater, Marcel Swart, F. Matthias Bickelhaupt, and Célia Fonseca Guerra
Org. Biomol. Chem., 2014, Volume 12, Number 26, Page 4691

Comments (0)

Please log in or register to comment.
Log in