DNA base pairs: the effect of the aromatic ring on the strength of the Watson–Crick hydrogen bonding

Celine Nieuwland; Michiel J. van Well; Laia Guillaumes; Anna de Vey Mestdagh; Lianne Dekker; Cynthia Nieuweboer; Sílvia Simon; Célia Fonseca Guerra

doi:10.1039/d5ob00819k

DNA base pairs: the effect of the aromatic ring on the strength of the Watson–Crick hydrogen bonding

Celine Nieuwland^*, Michiel J. van Well, Laia Guillaumes, Anna de Vey Mestdagh, Lianne Dekker, Cynthia Nieuweboer, Sílvia Simon, Célia Fonseca Guerra^*

^*Corresponding author for this work

Research output: Contribution to Journal › Article › Academic › peer-review

Abstract

The aromatic ring in DNA bases affects the Watson–Crick binding strength. Our quantum-chemical analyses, which compare the hydrogen bonding between the DNA bases and unsaturated analogs lacking the aromatic ring, reveal that this arises not from π-resonance assistance but from the electron-withdrawing (purines) or electron-donating (pyrimidines) effect of the heteroatom-containing ring on the frontier atoms. This electron redistribution modulates the electrostatics, steric Pauli repulsion, and σ-orbital interactions upon hydrogen bonding.

Original language	English
Pages (from-to)	9972-9979
Number of pages	8
Journal	Organic and Biomolecular Chemistry
Volume	23
Issue number	43
Early online date	26 Jul 2025
DOIs	https://doi.org/10.1039/d5ob00819k
Publication status	Published - 21 Nov 2025

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This journal is © The Royal Society of Chemistry, 2025

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title = "DNA base pairs: the effect of the aromatic ring on the strength of the Watson–Crick hydrogen bonding",

abstract = "The aromatic ring in DNA bases affects the Watson–Crick binding strength. Our quantum-chemical analyses, which compare the hydrogen bonding between the DNA bases and unsaturated analogs lacking the aromatic ring, reveal that this arises not from π-resonance assistance but from the electron-withdrawing (purines) or electron-donating (pyrimidines) effect of the heteroatom-containing ring on the frontier atoms. This electron redistribution modulates the electrostatics, steric Pauli repulsion, and σ-orbital interactions upon hydrogen bonding.",

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doi = "10.1039/d5ob00819k",

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T1 - DNA base pairs

T2 - the effect of the aromatic ring on the strength of the Watson–Crick hydrogen bonding

AU - Nieuwland, Celine

AU - van Well, Michiel J.

AU - Guillaumes, Laia

AU - de Vey Mestdagh, Anna

AU - Dekker, Lianne

AU - Nieuweboer, Cynthia

AU - Simon, Sílvia

AU - Fonseca Guerra, Célia

PY - 2025/11/21

Y1 - 2025/11/21

N2 - The aromatic ring in DNA bases affects the Watson–Crick binding strength. Our quantum-chemical analyses, which compare the hydrogen bonding between the DNA bases and unsaturated analogs lacking the aromatic ring, reveal that this arises not from π-resonance assistance but from the electron-withdrawing (purines) or electron-donating (pyrimidines) effect of the heteroatom-containing ring on the frontier atoms. This electron redistribution modulates the electrostatics, steric Pauli repulsion, and σ-orbital interactions upon hydrogen bonding.

AB - The aromatic ring in DNA bases affects the Watson–Crick binding strength. Our quantum-chemical analyses, which compare the hydrogen bonding between the DNA bases and unsaturated analogs lacking the aromatic ring, reveal that this arises not from π-resonance assistance but from the electron-withdrawing (purines) or electron-donating (pyrimidines) effect of the heteroatom-containing ring on the frontier atoms. This electron redistribution modulates the electrostatics, steric Pauli repulsion, and σ-orbital interactions upon hydrogen bonding.

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AN - SCOPUS:105016823869

SN - 1477-0520

VL - 23

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EP - 9979

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 43

ER -

DNA base pairs: the effect of the aromatic ring on the strength of the Watson–Crick hydrogen bonding

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