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

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

doi:10.1016/j.tet.2017.11.030

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

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

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Abstract

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.

Original language	English
Pages (from-to)	28-41
Number of pages	14
Journal	Tetrahedron
Volume	74
Issue number	1
DOIs	https://doi.org/10.1016/j.tet.2017.11.030
Publication status	Published - 04-01-2018

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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Vahdani Alviri, B., Pourayoubi, M., Saneei, A., Keikha, M., van der Lee, A., Crochet, A., Abdul Salam, A. A., Nečas, M., Fromm, K. M., Damodaran, K., & Jenny, T. A. (2018). Puckering behavior in six new phosphoric triamides containing aliphatic six- and seven-membered ring groups and a database survey of analogous ring-containing structures. Tetrahedron, 74(1), 28-41. https://doi.org/10.1016/j.tet.2017.11.030

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

abstract = "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.",

author = "{Vahdani Alviri}, Banafsheh and Mehrdad Pourayoubi and Anahid Saneei and Mojtaba Keikha and {van der Lee}, Arie and Aur{\'e}lien Crochet and {Abdul Salam,}, {Abdul Ajees} and Marek Ne{\v c}as and Fromm, {Katharina M.} and Krishnan Damodaran and Jenny, {Titus A.}",

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Vahdani Alviri, B, Pourayoubi, M, Saneei, A, Keikha, M, van der Lee, A, Crochet, A, Abdul Salam, AA, Nečas, M, Fromm, KM, Damodaran, K & Jenny, TA 2018, 'Puckering behavior in six new phosphoric triamides containing aliphatic six- and seven-membered ring groups and a database survey of analogous ring-containing structures', Tetrahedron, vol. 74, no. 1, pp. 28-41. https://doi.org/10.1016/j.tet.2017.11.030

TY - JOUR

T1 - Puckering behavior in six new phosphoric triamides containing aliphatic six- and seven-membered ring groups and a database survey of analogous ring-containing structures

AU - Vahdani Alviri, Banafsheh

AU - Pourayoubi, Mehrdad

AU - Saneei, Anahid

AU - Keikha, Mojtaba

AU - van der Lee, Arie

AU - Crochet, Aurélien

AU - Abdul Salam,, Abdul Ajees

AU - Nečas, Marek

AU - Fromm, Katharina M.

AU - Damodaran, Krishnan

AU - Jenny, Titus A.

PY - 2018/1/4

Y1 - 2018/1/4

N2 - 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.

AB - 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.

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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

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