The influence of substituents and the environment on the NMR shielding constants of supramolecular complexes based on A-T and A-U base pairs

Abril C. Castro, Marcel Swart, Célia Fonseca Guerra*

*Corresponding author for this work

Research output: Contribution to JournalArticleAcademicpeer-review

Abstract

In the present study, we have theoretically analyzed supramolecular complexes based on the Watson-Crick A-T and A-U base pairs using dispersion-corrected density functional theory (DFT). Hydrogen atoms H8 and/or H6 in the natural adenine and thymine/uracil bases were replaced, respectively, by substituents X8, Y6 = NH-, NH2, NH3 + (N series), O-, OH, OH2 + (O series), F, Cl or Br (halogen series). We examined the effect of the substituents on the hydrogen-bond lengths, strength and bonding mechanism, and the NMR shielding constants of the C2-adenine and C2-thymine/uracil atoms in the base pairs. The general belief in the literature that there is a direct connection between changes in the hydrogen-bond strength and the C2-adenine shielding constant is conclusively rejected by our computations.

Original languageEnglish
Pages (from-to)13496-13502
Number of pages7
JournalPhysical Chemistry Chemical Physics
Volume19
Issue number21
DOIs
Publication statusPublished - 25 Apr 2017

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