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Issue 11, 2005
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A theoretical study of the influence of nitrogen angular constraints on the properties of amides: rotation/inversion barriers and hydrogen bond accepting abilities of N-formylaziridine and -azirine

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Abstract

Theoretical calculations at the MP2/6-311++G** level have been carried out on three compounds: N,N-dimethylformamide (1), N-formylaziridine (2) and N-formylazirine (3). The barriers to rotation and inversion have been calculated, together with the properties of the nitrogen and oxygen atoms of these amides as hydrogen bond acceptors. The results provide a quantitative picture of the influence of ring strain on the properties of amides, with special emphasis on the effects associated with nitrogen pyramidalization.

Graphical abstract: A theoretical study of the influence of nitrogen angular constraints on the properties of amides: rotation/inversion barriers and hydrogen bond accepting abilities of N-formylaziridine and -azirine

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Publication details

The article was received on 06 Jul 2005, accepted on 24 Aug 2005 and first published on 14 Sep 2005


Article type: Paper
DOI: 10.1039/B509368F
Citation: New J. Chem., 2005,29, 1450-1453
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    A theoretical study of the influence of nitrogen angular constraints on the properties of amides: rotation/inversion barriers and hydrogen bond accepting abilities of N-formylaziridine and -azirine

    I. Alkorta, C. Cativiela, J. Elguero, A. M. Gil and A. I. Jiménez, New J. Chem., 2005, 29, 1450
    DOI: 10.1039/B509368F

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