C=O center dot center dot center dot pi Interaction: A Rare Noncovalent Binding in RC(O)NHP(O)[(NRR2)-R-1](2) Phosphoric Triamide Structures

CHAIJAN, Mahnaz Rostami, Mehrdad POURAYOUBI, Marek NEČAS and Krishnan DAMODARAN. C=O center dot center dot center dot pi Interaction: A Rare Noncovalent Binding in RC(O)NHP(O)[(NRR2)-R-1](2) Phosphoric Triamide Structures. Phosphorus, Sulfur, and Silicon and the related elements. Taylor and Francis Inc., 2015, vol. 190, 5-6, p. 911-917. ISSN 1042-6507. Available from: https://dx.doi.org/10.1080/10426507.2014.991826.

Basic information

Original name

C=O center dot center dot center dot pi Interaction: A Rare Noncovalent Binding in RC(O)NHP(O)[(NRR2)-R-1](2) Phosphoric Triamide Structures

Authors

CHAIJAN, Mahnaz Rostami (364 Islamic Republic of Iran), Mehrdad POURAYOUBI (364 Islamic Republic of Iran), Marek NEČAS (203 Czech Republic, guarantor, belonging to the institution) and Krishnan DAMODARAN (356 India)

Edition

Phosphorus, Sulfur, and Silicon and the related elements, Taylor and Francis Inc. 2015, 1042-6507

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Other information

Language

English

Type of outcome

Článek v odborném periodiku

Field of Study

10402 Inorganic and nuclear chemistry

Country of publisher

United Kingdom of Great Britain and Northern Ireland

Confidentiality degree

není předmětem státního či obchodního tajemství

Impact factor

Impact factor: 0.723

RIV identification code

RIV/00216224:14310/15:00086934

Organization unit

Faculty of Science

DOI

http://dx.doi.org/10.1080/10426507.2014.991826

UT WoS

000357323000056

Keywords in English

CSD; C=O center dot center dot center dot pi; phosphoric triamide; crystal structure

Tags

AKR, rivok

Tags

International impact, Reviewed

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Abstract

V originále

In the structure of C6F5C(O)NHP(O)[N(C2H5)(C6H11)](2), in addition to N-H center dot center dot center dot O=P hydrogen bond, the oxygen atom of P=O group is involved in the P=O center dot center dot center dot pi interaction (O-P center dot center dot center dot Cg = 3.507(1) angstrom, Cg is the centroid of C6F5 ring). Moreover, a noncovalent C=O center dot center dot center dot pi interaction takes part in the crystal packing, O-C center dot center dot center dot Cg = 3.159(1) angstrom. The C=O center dot center dot center dot pi interaction is the interesting feature of this structure, as a Cambridge Structural Database analysis (CSD; Allen, Acta Cryst. 2002, B58, 380-388) of 149 structures with a C(O)NHP(O)[N](2) skeleton shows that such an interaction exists only in 4 structures. The dihedral angle between the aromatic ring and the plane defined by the atoms of [C][N]C=O segment is 66.66 degrees. The C=O bond length in the present structure (of 1.2148(18) angstrom) is within the expected range for compounds with a C(O)NHP(O)[N](2) segment; however, due to the electronic effect caused by C6F5 group, it is in the region of the short bond lengths for analogous structures deposited in the CSD (1.18-1.26 angstrom). The P=O (1.4831(10) angstrom) and P-N (1.6340(12) angstrom and 1.6424(12) angstrom) bond lengths are standard for a phosphoric triamide structure and the P-N bond of C(O)NHP(O) segment (1.6980(12) angstrom) has an expected longer value relative to the other P-N bonds. The bond-angle sums around the tertiary nitrogen atoms (SUM = 2 x P-N-C + C-N-C) are 357.8 degrees and 352.0 degrees that show few deviations from the planar value of 360 degrees. The more pyramidal N atom is oriented so that the corresponding lone electron pair is anti with respect to the P=O group.