Acta Crystallographica Section C: Structural Chemistry, ( ISI ), Volume (74), No (7), Year (2018-7) , Pages (847-855)

Title : ( Evaluation of N—H···S and N—H···π interactions in O,Oʹ-diethyl N-(2,4,6-trimethylphenyl)thiophosphate: a combination of X-ray crystallographic and theoretical studies )

Authors: elham torabi farkhani , Mehrdad Pourayoubi , Mohammad Izadyar , P. V. Andreev , E. S. Shchegravina ,

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Abstract

In the crystal structure of O,Oʹ-diethyl N-(2,4,6-trimethylphenyl)thiophosphate, C13H22NO2PS, two symmetrically independent thiophosphoramide molecules are linked through N—H…S and N—H…π hydrogen bonds to form a noncentrosymmetric dimer, with Zʹ = 2. The strengths of the hydrogen bonds were evaluated using density functional theory (DFT) at the M06-2X level within the 6-311++G(d,p) basis set, and by considering the quantum theory of atoms in molecules (QTAIM). It was found that the N—H…S hydrogen bond is slightly stronger than the N—H…π hydrogen bond. This is reflected in differences between the calculated N—H stretching frequencies of the isolated molecules and the frequencies of the same N—H units involved in the different hydrogen bonds of the hydrogen-bonded dimer. For these hydrogen bonds, the corresponding charge transfers, i.e. lp (or π)→σ*, were studied, according to the second-order perturbation theory in natural bond orbital (NBO) methodology. Hirshfeld surface analysis was applied for a detailed investigation of all the contacts participating in the crystal packing.

Keywords

, thiophosphoramide; X, ray crystallography; DFT calculations; NBO; crystal structure; QTAIM; Hirshfeld surface analysis; computational chemistry
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@article{paperid:1069260,
author = {Torabi Farkhani, Elham and Pourayoubi, Mehrdad and Izadyar, Mohammad and P. V. Andreev and E. S. Shchegravina},
title = {Evaluation of N—H···S and N—H···π interactions in O,Oʹ-diethyl N-(2,4,6-trimethylphenyl)thiophosphate: a combination of X-ray crystallographic and theoretical studies},
journal = {Acta Crystallographica Section C: Structural Chemistry},
year = {2018},
volume = {74},
number = {7},
month = {July},
issn = {2053-2296},
pages = {847--855},
numpages = {8},
keywords = {thiophosphoramide; X-ray crystallography; DFT calculations; NBO; crystal structure; QTAIM; Hirshfeld surface analysis; computational chemistry},
}

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%0 Journal Article
%T Evaluation of N—H···S and N—H···π interactions in O,Oʹ-diethyl N-(2,4,6-trimethylphenyl)thiophosphate: a combination of X-ray crystallographic and theoretical studies
%A Torabi Farkhani, Elham
%A Pourayoubi, Mehrdad
%A Izadyar, Mohammad
%A P. V. Andreev
%A E. S. Shchegravina
%J Acta Crystallographica Section C: Structural Chemistry
%@ 2053-2296
%D 2018

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