The first C(O)NHP(O)-based phosphoric triamide structure with an N‒H···π hydrogen bonding: A combination of X-ray crystallography and theoretical study to evaluate the strength of hydrogen bonds

A combined X-ray crystallography and theoretical study of N—H...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

“…Quantum chemical calculations were also applied to an evaluation of N-HÁ Á ÁY P (Y = O and S) hydrogen-bond strengths, which in a typical N-HÁ Á ÁS P hydrogen bond examined is about one-half with respect to N-HÁ Á ÁO P, e.g. 4.00 kcal mol À1 (1 kcal mol À1 = 4.184 kJ mol À1 ) in [2,4,6-(CH 3 ) 3 C 6 H 2 NH]P(S)[OCH 2 CH 3 ] 2 (Torabi Farkhani et al, 2018) and 6.99 kcal mol À1 in [(4-CH 3 O)C 6 H 4 C(O)NH]-P(O)[NHCH 2 C 6 H 4 (4-CH 3 )] 2 (Taherzadeh et al, 2017). Furthermore, Shainyan et al (2010) reported the calculated hydrogen-bond energies for N-HÁ Á ÁS and N-HÁ Á ÁO within the ranges 3.8-6.0 and 4.8-8.6 kcal mol À1 , respectively, for some sulfonamide derivatives.…”

Competing and directing interactions in new phosphoramide/thiophosphoramide structures: energy considerations and evidence for CH⋯HC contacts and aliphatic–aromatic stacking

“…The reasons for the selection of these two structures 35,36 are (i) the low electrostatic potentials of both HB donor (C-H groups) and acceptor (sulfur atom) sites, which are expected to minimize the strengths of HBs, and (ii) the large number of CH units, which facilitate the formation of C-H⋯H-C interactions and raise their importance in the total interactions.…”

Evaluation of N—H...S and N—H...π interactions inO,O′-diethylN-(2,4,6-trimethylphenyl)thiophosphate: a combination of X-ray crystallographic and theoretical studies

“…So, it is necessary to use the most contemporary quantum chemical methods for a prediction of the changes in various properties of the interacting molecular systems which may provide complementary data to the experimental ones, and also, in some cases, to even initiate reanalysis of the experimental data and their reinterpretation (Pourayoubi et al, 2013). Continuing our previous studies on a variety of intermolecular interactions (Hamzehee et al, 2017;Taherzadeh et al, 2017), in this article we report on the synthesis, spectroscopic characterization and X-ray crystallography of [2,4,6-(CH 3 ) 3 C 6 H 2 NH]P(S)[OCH 2 CH 3 ] 2 (Scheme 1), namely O,O 0 -diethyl N-(2,4,6-trimethylphenyl)thiophosphate. The results of a quantum chemistry study on the hydrogenbond formation in the dimer are presented.…”