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Phosphorus, Sulfur, and Silicon and the Related Elements Volume 191, 2016 - Issue 3: Reinhard Schmutzler Special Issue
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Original Articles

Molecular and electronic structure of 1,3,2-diazaphosphinine derivatives

Mark I. PovolotskiiInstitute of Organic Chemistry, National Academy of Sciences of Ukraine, Kyiv, Ukraine
,
Oleg V. ShablykinInstitute of Bioorganic Chemistry and Petrochemistry, National Academy of Sciences of Ukraine, Kyiv, Ukraine
,
Eduard B. RusanovInstitute of Organic Chemistry, National Academy of Sciences of Ukraine, Kyiv, Ukraine
&
Alexander B. RozhenkoInstitute of Organic Chemistry, National Academy of Sciences of Ukraine, Kyiv, Ukraine;Fakultät für Chemie, Universität Bielefeld, Bielefeld, GermanyCorrespondence[email protected]
Pages 399-404 | Received 01 Jul 2015, Accepted 19 Aug 2015, Published online: 17 Mar 2016
 
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GRAPHICAL ABSTRACT

ABSTRACT

Structure of 1,3,2-diazaphosphinine heterocyclic system was studied using quantum chemical calculations and X-ray diffraction method for one derivative. It was found that two P–N single bonds were different in their nature: one of them turned out to be significantly shorter and stronger, whereas the other one is longer and more diffused. The found effect is strengthened by π-donor substituents. The effect was interpreted by equilibrium of Lewis structures and analyzing the charge distribution by the NBO approach. The observed effect can be considered as the special form of π-conjugation in the heterocycles with the phosphorus (V) atom included.

Acknowledgments

The authors are grateful to Prof. Dr. Uwe Manthe and Dr. Thorsten Tönsing, University of Bielefeld (Germany), for access to the computer cluster and Gaussian 03 packets of programs and also for technical support for the calculations.

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