Extensive analysis of N-H center dot center dot center dot O hydrogen bonding in four classes of phosphorus compounds: a combined experimental and database study

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Authors

HAMZEHEE Farahnaz POURAYOUBI Mehrdad NEČAS Marek CHOQUESILLO-LAZARTE Duane

Year of publication 2017
Type Article in Periodical
Magazine / Source ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY
MU Faculty or unit

Faculty of Science

Citation
Web http://scripts.iucr.org/cgi-bin/paper?S2053229617001516
Doi http://dx.doi.org/10.1107/S2053229617001516
Keywords phosphorus compound; crystal structure; hydrogen bonding; Cambridge Structural Database; positive/negative charge-assisted N-H center dot center dot center dot O hydrogen bonds
Description The N-H center dot center dot center dot O hydrogen bond is the characteristic interaction in the crystal structures of N-benzyl-P-phenyl-N'-(p-tolyl) phosphonic diamide, C20H21N2OP or (C6H5)P(O)(NHCH2C6H5)(NHC6H4-p-CH3), (I), diphenylphosphinic 1-methylpropylamide, C16H20NOP or (C6H5)(2)P(O)[NHCH(CH3)(C2H5)], (II), (S)-1-phenylethylammonium N-[(S)-1-phenylethyl] phenylphosphonamidate, C8H12N+center dot-C14H15NO2P- or [S-(C6H5)CH(CH3)NH3][(C6H5)P(O){S-NHCH(CH3)(C6H5)}(O)], (III), and (4-methylbenzyl) ammonium diphenylphosphinate, C8H12N+center dot-C12H10O2P- or [4-CH3-C6H4CH2NH3][(C6H5)(2)P(O)(O)], (IV). This article focuses on the N-H center dot center dot center dot O hydrogen bonds by considering the structures of (I), (II), (III) and (IV), and reviewing their analogous compounds, including 43 (C)P(O)(N)(2), 102 (C)(2)P(O)(N), 31 (C) P(O)(N)(O) and 96 (C)(2)P(O)(O) structures, deposited in the Cambridge Structural Database (CSD). For the structures with a (C) P(O)(N) 2 segment, only neutral hydrogen bonds were found in the CSD. The other three classes of compounds included both neutral and 'charge-assisted' hydrogen bonds, and the (C) 2P(O)(O) structures were particularly noticeable for a high number of cation-anion compounds. The overall tendencies of N center dot center dot center dot O distances in neutral and cation-anion compounds were compared. The N-H center dot center dot center dot O hydrogen-bond angles were also analyzed for the four classes of phosphorus compounds.
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