A combined X-ray crystallography and theoretical study of N-H center dot center dot center dot OX (X is =P and -C) hydrogen bonds in two new structures with a (C-O)(2)(N)-P(=Y) (Y is O and S) skeleton

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ALVIRI Banafsheh Vahdani POURAYOUBI Mehrdad FARHADIPOUR Abolghasem NEČAS Marek BERTOLASI Valerio

Druh Článek v odborném periodiku
Časopis / Zdroj ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY
Fakulta / Pracoviště MU

Přírodovědecká fakulta

Citace
Doi http://dx.doi.org/10.1107/S2053229618014006
Klíčová slova phosphoramide; thiophosphoramide; X-ray diffraction; N-H center dot center dot center dot O hydrogen bond; crystal structure; quantum chemical calculations; Hirshfeld surface analysis
Popis The crystal structures of N,N'-(cyclohexane-1,4-diyl)bis(O,O'-diphenylphosphoramide), C30H32N2O6P2 or (C6H5O)(2)P(O)(1-NH)(C6H10)(4-NH)P(O)(OC6H5)(2), (I), and N,N'-(1,4-phenylene)bis(O,O'-dimethylthiophosphoramide), C10H18N2O4P2S2 or (CH3O)(2)P(S)(1-NH)(C6H4)(4-NH) P(S)(OCH3)(2), (II), have been investigated. In the structure of (I), with an (O)(2)(N)P(O) skeleton, two symmetry-independent phosphoramide molecules are linked through N-H center dot center dot center dot O=P hydrogen bonds. In the structure of (II), with an (O) 2(N) P(S) skeleton, the ester O atoms take part in N-H center dot center dot center dot O-C hydrogen bonds as acceptors; the P=S groups do not participate in hydrogen-bonding interactions. The strengths of these hydrogen bonds were evaluated, using quantum chemical calculations with the GAUSSIAN09 software package at the B3LYP/6-311G(d,p) level of theory. For this, LP(O) to sigma*(NH) charge transfers were studied, according to the second-order perturbation theory in natural bond orbital (NBO) methodology, for a three-component cluster of hydrogen-bonded molecules for both structures, including all of the independent N-H center dot center dot center dot O hydrogen bonds observed in the crystal packing. The details of the intermolecular interactions were studied by Hirshfeld surface maps and two-dimensional fingerprint plots.
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