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@article{964974,
author = {Pourayoubi, Mehrdad and Nečas, Marek and Negari, Monireh},
article_number = {2},
doi = {http://dx.doi.org/10.1107/S0108270111052097},
keywords = {phenyl bis(2-chlorobenzylamido)phosphinate; crystal structures},
language = {eng},
issn = {0108-2701},
journal = {Acta Crystallographica Section C: Crystal Structure Communications},
title = {The double H-atom acceptability of the P=O group in new X P(O)(NHCH2C6H4-2-Cl)2 phosphoramidates [X = C6H5O- and CF3C(O)NH-]: a database analysis of compounds having a P(O)(NHR ) group},
url = {http://dx.doi.org/10.1107/S0108270111052097},
volume = {68},
year = {2012}
}
TY - JOUR
ID - 964974
AU - Pourayoubi, Mehrdad - Nečas, Marek - Negari, Monireh
PY - 2012
TI - The double H-atom acceptability of the P=O group in new X P(O)(NHCH2C6H4-2-Cl)2 phosphoramidates [X = C6H5O- and CF3C(O)NH-]: a database analysis of compounds having a P(O)(NHR ) group
JF - Acta Crystallographica Section C: Crystal Structure Communications
VL - 68
IS - 2
SP - o51-o56
EP - o51-o56
SN - 01082701
KW - phenyl bis(2-chlorobenzylamido)phosphinate
KW - crystal structures
UR - http://dx.doi.org/10.1107/S0108270111052097
N2 - In the hydrogen-bond patterns of phenyl bis(2-chlorobenzylamido)phosphinate, C20H19Cl2N2O2P, (I), and N,N'-bis(2-chlorobenzyl)-N''-(2,2,2-trifluoroacetyl)phosphoric triamide, C16H15Cl2F3N3O2P, (II), the O atoms of the related phosphoryl groups act as double H-atom acceptors, so that the P=O(H-N)2 hydrogen bond in (I) and the P=O(H-Namide)2 and C=OH-NC(O)NHP(O) hydrogen bonds in (II) are responsible for the aggregation of the molecules in the crystal packing. The presence of a double H-atom acceptor centre is a result of the involvement of a greater number of H-atom donor sites with a smaller number of H-atom acceptor sites in the hydrogen-bonding interactions. This article also reviews structures having a P(O)NH group, with the aim of finding similar three-centre hydrogen bonds in the packing of phosphoramidate compounds. This analysis shows that the factors affecting the preference of the above-mentioned O atom to act as a double H-atom acceptor are: (i) a higher number of H-atom donor sites relative to H-atom acceptor centres in molecules with P(=O)(NH)3, (N)P(=O)(NH)2, C(=O)NHP(=O)(NH)2 and (NH)2P(=O)OP(=O)(NH)2 groups, and (ii) the remarkable H-atom acceptability of this atom relative to the other acceptor centre(s) in molecules containing an OP(=O)(NH)2 group, with the explanation that the N atom bound to the P atom in almost all of the structures found does not take part in hydrogen bonding as an acceptor. Moreover, the differences in the H-atom acceptability of the phosphoryl O atom relative to the O atom of the alkoxy or phenoxy groups in amidophosphoric acid esters may be illustrated by considering the molecular packing of compounds having (O)2P(=O)(NH) and (O)P(=O)(NH)(N)groups, in which the unique N-H unit in the above-mentioned molecules almost always selects the phosphoryl O atom as a partner in forming hydrogen-bond interactions.
ER -
POURAYOUBI, Mehrdad, Marek NEČAS a Monireh NEGARI. The double H-atom acceptability of the P=O group in new X P(O)(NHCH2C6H4-2-Cl)2 phosphoramidates [X = C6H5O- and CF3C(O)NH-]: a database analysis of compounds having a P(O)(NHR ) group. \textit{Acta Crystallographica Section C: Crystal Structure Communications}. 2012, roč.~68, č.~2, s.~o51-o56, 6 s. ISSN~0108-2701. Dostupné z: https://dx.doi.org/10.1107/S0108270111052097.
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