Issue 11, 2005
From the journal:

New Journal of Chemistry

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

Ibon Alkorta,*a   Carlos Cativiela,b   José Elguero,a   Ana M. Gilb  and  Ana I. Jiménezb  

* Corresponding authors

a Instituto de Química Médica (CSIC), Juan de la Cierva, 3, Spain
E-mail: ibon@iqm.csic.es
Fax: +34 91 564-4853

b Departamento de Química Orgánica, Instituto de Ciencia de Materiales de Aragón, Universidad de Zaragoza - CSIC, Spain

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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Article information

DOI
https://doi.org/10.1039/B509368F
Article type
Paper
Submitted
06 Jul 2005
Accepted
24 Aug 2005
First published
14 Sep 2005

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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