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The typical crystal structures of a few representative α‐aryl‐α‐hydroxyphosphonates
Author(s) -
Rádai Zita,
Kiss Nóra Zsuzsa,
Czugler Mátyás,
Karaghiosoff Konstantin,
Keglevich György
Publication year - 2019
Publication title -
acta crystallographica section c
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.304
H-Index - 17
ISSN - 2053-2296
DOI - 10.1107/s2053229619001839
Subject(s) - aryl , crystal structure , crystal (programming language) , chemistry , materials science , crystallography , computer science , organic chemistry , programming language , alkyl
The crystal structures of seven α‐aryl‐α‐hydroxyphosphonates synthesized by the Pudovik reaction of substituted benzaldehydes and dialkyl phosphites, namely dimethyl [(hydroxy)(phenyl)methyl]phosphonate, C 9 H 13 O 4 P, dimethyl [(3,4‐dimethoxyphenyl)(hydroxy)methyl]phosphonate, C 11 H 17 O 6 P, dimethyl (1‐hydroxy‐1‐phenylethyl)phosphonate, C 10 H 15 O 4 P, dimethyl [1‐hydroxy‐1‐(4‐nitrophenyl)ethyl]phosphonate, C 10 H 14 NO 6 P, dibenzyl [hydroxy(2‐nitrophenyl)methyl]phosphonate, C 21 H 20 NO 6 P, dibenzyl [(3‐chlorophenyl)(hydroxy)methyl]phosphonate, C 21 H 20 ClO 4 P, and dibenzyl [hydroxy(4‐methylphenyl)methyl]phosphonate, C 22 H 23 O 4 P, were studied to gain a better understanding of the organization in this type of molecule in the solid state. The crystals obtained for this series of compounds show a balance between C—OH…O=P chain‐linked packing and the dimeric types of hydrogen‐bond bridges of intermolecular pairs of such functions. The description is based on primary graph‐set descriptors. Using graph‐set descriptors one level deeper ( i.e. secondary graph sets of the C—H…O type) revealed a similarity in the graph‐set descriptors, suggesting a fine interplay of substituent‐ and shape‐dependent effects on strong–weak interactions. It seems that the formation of chains or dimers is governed not only by the presence of a tertiary Cα atom, but also by the nature and crowding of the ortho substituents of the α‐aryl group.