pi-Stacked Quadruply Hydrogen-Bonded Dimers: pi-Stacking Influences H-Bonding

D. Guo; H. Zuilhof; R.P. Sijbesma

doi:10.1021/ol048821m

pi-Stacked Quadruply Hydrogen-Bonded Dimers: pi-Stacking Influences H-Bonding

D. Guo, H. Zuilhof, R.P. Sijbesma

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

53 Citations (Scopus)

Abstract

The effects of pi-stacking on the stability of multiply hydrogen-bonded systems are investigated using hybrid DFT calculations on pi-stacked quadruply H-bonded dimers of ureidopyrimidinone in its different tautomeric forms. Both the strengths of the hydrogen bonds and the relative occurrence of tautomers are influenced by pi-stacking; electrostatics and natural bond orbital analysis are used to explain these observations. Finally, these conclusions are independent of the precise nature of the multiply hydrogen-bonded systems, including the DNA base pairs.

Original language	English
Pages (from-to)	3667-3670
Journal	Organic Letters
Volume	6
Issue number	21
DOIs	https://doi.org/10.1021/ol048821m
Publication status	Published - 2004

Keywords

density-functional theory
ab-initio
supramolecular polymers
guanine-cytosine
base-pairs
complexes
model
systems
thymine

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10.1021/ol048821m

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title = "pi-Stacked Quadruply Hydrogen-Bonded Dimers: pi-Stacking Influences H-Bonding",

abstract = "The effects of pi-stacking on the stability of multiply hydrogen-bonded systems are investigated using hybrid DFT calculations on pi-stacked quadruply H-bonded dimers of ureidopyrimidinone in its different tautomeric forms. Both the strengths of the hydrogen bonds and the relative occurrence of tautomers are influenced by pi-stacking; electrostatics and natural bond orbital analysis are used to explain these observations. Finally, these conclusions are independent of the precise nature of the multiply hydrogen-bonded systems, including the DNA base pairs.",

keywords = "density-functional theory, ab-initio, supramolecular polymers, guanine-cytosine, base-pairs, complexes, model, systems, thymine",

author = "D. Guo and H. Zuilhof and R.P. Sijbesma",

year = "2004",

doi = "10.1021/ol048821m",

language = "English",

volume = "6",

pages = "3667--3670",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

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T1 - pi-Stacked Quadruply Hydrogen-Bonded Dimers: pi-Stacking Influences H-Bonding

AU - Guo, D.

AU - Zuilhof, H.

AU - Sijbesma, R.P.

PY - 2004

Y1 - 2004

N2 - The effects of pi-stacking on the stability of multiply hydrogen-bonded systems are investigated using hybrid DFT calculations on pi-stacked quadruply H-bonded dimers of ureidopyrimidinone in its different tautomeric forms. Both the strengths of the hydrogen bonds and the relative occurrence of tautomers are influenced by pi-stacking; electrostatics and natural bond orbital analysis are used to explain these observations. Finally, these conclusions are independent of the precise nature of the multiply hydrogen-bonded systems, including the DNA base pairs.

AB - The effects of pi-stacking on the stability of multiply hydrogen-bonded systems are investigated using hybrid DFT calculations on pi-stacked quadruply H-bonded dimers of ureidopyrimidinone in its different tautomeric forms. Both the strengths of the hydrogen bonds and the relative occurrence of tautomers are influenced by pi-stacking; electrostatics and natural bond orbital analysis are used to explain these observations. Finally, these conclusions are independent of the precise nature of the multiply hydrogen-bonded systems, including the DNA base pairs.

KW - density-functional theory

KW - ab-initio

KW - supramolecular polymers

KW - guanine-cytosine

KW - base-pairs

KW - complexes

KW - model

KW - systems

KW - thymine

U2 - 10.1021/ol048821m

DO - 10.1021/ol048821m

M3 - Article

VL - 6

SP - 3667

EP - 3670

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 21

ER -