Puckering behavior in six new phosphoric triamides containing aliphatic six- and seven-membered ring groups and a database survey of analogous ring-containing structures

Alviri, Banafsheh Vahdani; Pourayoubi, Mehrdad; Saneei, Anahid; Keikha, Mojtaba; Lee, Arie van der; Crochet, Aurélien; Ajees, A. Abdul; Nečas, Marek; Fromm, Katharina M.; Damodaran, Krishnan; Jenny, Titus A.

doi:10.1016/j.tet.2017.11.030

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Puckering behavior in six new phosphoric triamides containing aliphatic six- and seven-membered ring groups and a database survey of analogous ring-containing structures

Alviri, Banafsheh Vahdani Department of Chemistry, Faculty of Sciences, Ferdowsi University of Mashhad, Iran
Pourayoubi, Mehrdad Department of Chemistry, Faculty of Sciences, Ferdowsi University of Mashhad, Iran
Saneei, Anahid Department of Chemistry, Faculty of Sciences, Ferdowsi University of Mashhad, Iran
Keikha, Mojtaba Department of Chemistry, Faculty of Sciences, Ferdowsi University of Mashhad, Iran
Lee, Arie van der Institut Européen des Membranes, Universitée de Montpellier, France
Crochet, Aurélien Fribourg Centre for Nanomaterials, FriMat, University of Fribourg, Department of Chemistry, Fribourg, Switzerland
Ajees, A. Abdul Department of Atomic and Molecular Physics, Manipal Institute of Technology, Manipal University, Karnataka, India
Nečas, Marek Department of Chemistry, Masaryk University, Kotlarska 2, Brno, Czech Republic - CEITEC - Central European Institute of Technology, Masaryk University, Kamenice, Brno, Czech Republic
Fromm, Katharina M. Fribourg Centre for Nanomaterials, FriMat, University of Fribourg, Department of Chemistry, Fribourg, Switzerland
Damodaran, Krishnan Department of Chemistry, University of Pittsburgh, Pittsburgh, USA
Jenny, Titus A. Department of Chemistry, University of Fribourg, Switzerland

04.01.2018

Published in:

Tetrahedron. - 2018, vol. 74, no. 1, p. 28–41

English The influence of a N heteroatom on the ring conformations of six- and seven- membered aliphatic rings in six new C(O)NHP(O)-based phosphoric triamide structures (analysed by X-ray crystallography) is investigated. Additionally the influence of steric and crystal packing effects is also studied by the analysis of Hirshfeld surfaces. The results are compared to analogous structures with three- to seven- aliphatic membered rings deposited in the Cambridge Structural Database. In the newly determined structures, the six-membered rings only show the near-chair conformation with a maximum deviation of the θ puckering parameter of 4.4° from the ideal chair value of 0°/180°, while the seven-membered rings are found in different conformations such as near-chair, twist chair and twist sofa.

Faculty

Faculté des sciences et de médecine

Department

Département de Chimie

Language