Pi-stacked quadruply hydrogen-bonded dimers: pi-stacking influences H-bonding

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

doi:10.1021/ol048821m

Pi-stacked quadruply hydrogen-bonded dimers: pi-stacking influences H-bonding

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

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

61 Citations (Scopus)

Abstract

The effects of p-stacking on the stability of multiply hydrogen-bonded systems are investigated using hybrid DFT calculations on p-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 p-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

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title = "Pi-stacked quadruply hydrogen-bonded dimers: pi-stacking influences H-bonding",

abstract = "The effects of p-stacking on the stability of multiply hydrogen-bonded systems are investigated using hybrid DFT calculations on p-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 p-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.",

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

year = "2004",

doi = "10.1021/ol048821m",

language = "English",

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journal = "Organic Letters",

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publisher = "American Chemical Society",

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T1 - Pi-stacked quadruply hydrogen-bonded dimers: pi-stacking influences H-bonding

AU - Guo, D.

AU - Sijbesma, R.P.

AU - Zuilhof, H.

PY - 2004

Y1 - 2004

N2 - The effects of p-stacking on the stability of multiply hydrogen-bonded systems are investigated using hybrid DFT calculations on p-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 p-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 p-stacking on the stability of multiply hydrogen-bonded systems are investigated using hybrid DFT calculations on p-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 p-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.

U2 - 10.1021/ol048821m

DO - 10.1021/ol048821m

M3 - Article

SN - 1523-7060

VL - 6

SP - 3667

EP - 3670

JO - Organic Letters

JF - Organic Letters

IS - 21

ER -

Pi-stacked quadruply hydrogen-bonded dimers: pi-stacking influences H-bonding

Abstract

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