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@article{1338639,
author = {Chaijan, Mahnaz Rostami and Pourayoubi, Mehrdad and Nečas, Marek and Damodaran, Krishnan},
article_number = {5-6},
doi = {http://dx.doi.org/10.1080/10426507.2014.991826},
keywords = {CSD; C=O center dot center dot center dot pi; phosphoric triamide; crystal structure},
language = {eng},
issn = {1042-6507},
journal = {Phosphorus, Sulfur, and Silicon and the related elements},
title = {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},
volume = {190},
year = {2015}
}
TY - JOUR
ID - 1338639
AU - Chaijan, Mahnaz Rostami - Pourayoubi, Mehrdad - Nečas, Marek - Damodaran, Krishnan
PY - 2015
TI - 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
JF - Phosphorus, Sulfur, and Silicon and the related elements
VL - 190
IS - 5-6
SP - 911-917
EP - 911-917
PB - Taylor and Francis Inc.
SN - 10426507
KW - CSD
KW - C=O center dot center dot center dot pi
KW - phosphoric triamide
KW - crystal structure
N2 - 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.
ER -
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. \textit{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.
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