The Nature of the Hydroxyl Group pi-Electron Interaction. Repulsive Instead of Attractive?

Abraham, Raymond J.; Bakke, Jan M.; Brobakke, Kristin; Carlberg, Georg E.; Sterner, Olov; Wickberg, Börje

doi:10.3891/acta.chem.scand.37b-0865

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2011

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Cited by 16 publications

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“…Apparently, the oxygen lone-pair electrons can stabilize a planar conformation if the oxygen is attached directly to the ring but not if the oxy gen atom is ,,ne carbon atom removed from the ring. 12 …”

Section: Discussionmentioning

confidence: 99%

Determination of the Minimum Energy Conformations of Benzyl Alcohol and 2-Phenethyl Alcohol

Im¹,

Bernstein²

1989

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Section: Discussionmentioning

confidence: 99%

Determination of the Minimum Energy Conformations of Benzyl Alcohol and 2-Phenethyl Alcohol

Im¹,

Bernstein²

1989

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ChemInform Abstract: THE NATURE OF THE HYDROXYL GROUP Π‐ELECTRON INTERACTION. REPULSIVE INSTEAD OF ATTRACTIVE?

Abraham¹,

Bakke²

1984

Chemischer Informationsdienst

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7‐Arylnorbornanes: Model Compounds for the Study of CH···π and OH···π Interactions

2011

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Keywords: Conformation analysis / Molecular modeling / Noncovalent interactions / Pi interactions / Density functional calculationsPreorganised 7-arylnorbornanes were selected as suitable model compounds for the study of CH···π and OH···π interactions. The most stable conformation of these derivatives favours such interactions by avoiding secondary hydrogen bonds between the oxygen atoms and the ortho-H of the aryl rings in the planar conformation as well as by increasing the gauche/trans ratio for steric reasons. The rotational barriers of the studied compounds are higher when electron-donor substituents are placed at the para position of the aryl ring. The trend of the electronic effects exerted by the substituents

show abstract

The Nature of the Hydroxyl Group pi-Electron Interaction. Repulsive Instead of Attractive?

Cited by 16 publications

References 0 publications

Determination of the Minimum Energy Conformations of Benzyl Alcohol and 2-Phenethyl Alcohol

Determination of the Minimum Energy Conformations of Benzyl Alcohol and 2-Phenethyl Alcohol

ChemInform Abstract: THE NATURE OF THE HYDROXYL GROUP Π‐ELECTRON INTERACTION. REPULSIVE INSTEAD OF ATTRACTIVE?

7‐Arylnorbornanes: Model Compounds for the Study of CH···π and OH···π Interactions

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